There have been few more colourful characters to cross the Australian or New Zealand Turf than ‘Lucky Dan’ O’Brien, owner and trainer of the 1895 A.J.C. Derby winner, Bob Ray. Most racing men today recognise the name Dan O’Brien as the first owner of Carbine, but there was so much more to his colourful life in racing than that chapter. He was born on 16 January 1847 in Lonsdale-street, between Elizabeth and Queen-streets, in the inner Melbourne suburb of Carlton; it was roughly in line with where Kirk’s Bazaar stood for so long on the north side of the Bourke-street hill in the area now occupied by Hardware-street. How fitting that the man who was to become perhaps the shrewdest horsetrader of his times on both sides of the Tasman, should have been born within a stone’s throw of the most famous bazaar in the colonies for the buying and selling of draught, saddle and thoroughbred horses. Every week in the years of O’Brien’s early childhood, hundreds of horses of all breeds were driven down from the country and hills for sale there. At the northern end of the bazaar was a ‘bull-ring’ for unbroken horses while a shoeing forge stood at the Little Bourke-street end, or what is now Hardware-street. This was then a tan strip where the horses were paraded for the benefit of buyers. These were scenes familiar to O’Brien in his childhood.
The location made sense for Dan O’Brien’s father, Denis, who was an overland horse and cattle drover, and mother, Anne. Daniel O’Brien was of Irish parentage and inherited to the full the Irishman’s natural affinity with the horse. Alas, young Daniel was orphaned at the age of ten and was adopted by an uncle, David Gorman, and he spent the balance of his youth in Beveridge, a small town along the Hume Highway some 26 miles north of Melbourne. Named after a Scottish sheep farmer who built the Hunters’ Tryste Inn in 1845, Beveridge is best known as the birthplace of the bushranger, Ned Kelly, who was seven years younger than Daniel O’Brien. O’Brien often saw the notorious Kelly boys in his youth. His first association in a racing stable was at Beveridge, and his abilities with horses eventually landed him a job as a jockey working in Melbourne with the Maribyrnong Stud. It was in the palmy days of the establishment when the brothers Charles (CB) and Hurtle Fisher owned the best team of racehorses in the land prepared by William Filgate, and a stud that had no equal outside of England itself. O’Brien rode the unplaced Fisherman’s Daughter for Hurtle Fisher in the 1865 A.J.C. Derby, in what was generally regarded at the time as the first official running of the race. O’Brien’s successes in the saddle under the rose and black banner of Maribyrnong were circumscribed by the fact that he enjoyed only second call behind Joe Morrison, but nonetheless, he did win the 1865 Victoria Oaks on Lady Heron and the inaugural running of the Champagne Stakes in 1866 at Randwick on Fishhook, among other good races for the stable.
When landing, Fishhook with 8 st. 7lb, a winner of the A.J.C. Champagne Stakes as the 6/4 favourite, Dan O’Brien was nineteen and already getting too heavy to pick-up many rides on the flat. It was within a year or two that increasing weight and the lure of the New Zealand goldfields saw him cross the Tasman to try his luck. In the roaring days during and immediately after the rush in Central Otago, gambling in all of its manifestations thrived. It was the site of New Zealand’s most significant gold strike and was at its peak during the years of 1861-1864. Starting at Gabriel’s Gully and rapidly spreading, it saw Dunedin quickly grow to be the country’s largest city. The gold fever and panic had somewhat subsided by the time O’Brien arrived, but it was very much a lively place in the wake of the rush. There were flat races and cross-country hurdles as well as trotting events for horses; and foot races aplenty for men of an athletic bent. Dan O’Brien, a natural athlete and a young man in a hurry, made himself into the right person in the right place at the right time and tried them all, making and losing small fortunes as he was swept along in the frenzy of the gold rush.
There were some good racehorses tried on the goldfields’ courses too, and one horse that O’Brien trained and rode there was Flying Jib, winner of the 1868 New Zealand Derby and Cup. Having observed the methods of William Filgate and the Maribyrnong Stud first hand, O’Brien knew how to prepare a racehorse. By around 1875, O’Brien had transferred his adventures to Christchurch and teamed up with Jack Ward, a professional wrestler who owned a first-class racehorse in Tambourini. O’Brien trained and rode the horse to a string of wins for Ward before buying him, and then proceeded to win more good races under his own colours including the 1874 New Zealand Cup and 1875 Wellington Cup. Tambourini won some thirty races from fifty-seven starts and did much to lay the foundation of O’Brien’s fortune. When it came to riding and training, O’Brien was from the beginning a man of disciplined energy, distilled from the trials of his somewhat stormy youth, and it was to give him an enduring strength. I might add that the colours O’Brien chose to register as his own were the very same rose and black stripes of his old employer at Maribyrnong. And what luck O’Brien was to enjoy with that livery! Fishhook was the next good galloper he got his hands on – a son of Traducer that he named after his old Maribyrnong favourite and a horse with whom he won the Dunedin Cup and Forbury Handicap of 1877. O’Brien then proceeded to sell Fishhook and all his horses to the English cricketer W. F. Neilson in November 1878 after the Christchurch meeting, although he did repurchase Fishhook some two years later for 250 guineas. But by then the horse’s best days were behind him. In total, Fishhook won 27 races from 51 starts and £2,787. The end came when he broke his leg running in the Inangahua Cup and had to be shot.
Testimony to Dan O’Brien’s judgement of a racehorse next came with Tasman, a son St Albans and Zillah. Bred by John Field of Deloraine, Tasmania, and foaled in 1878, Tasman was sold as a yearling for £35 to a Mr C. G. Eady. On the day of the sale when a number of yearlings were knocked down, the perspicacious correspondent for the Cornwall Chronicle expressed the opinion that Eady ‘got the bargain of the day’. And he did although he wasn’t to derive the greatest benefit. Eady sent the horse to New Zealand where Tasman passed through another owner’s hands before Dan O’Brien got him for 100 guineas. Tasman won thirty-one races for O’Brien including the first New Zealand Cup (previously called the Canterbury Jockey Club Handicap) in 1883, the Timaru Cups of 1883 and 1884, and the Wellington Cup and Dunedin Jockey Club Handicap in 1885. He proved quite a bargain. Tasman augmented the O’Brien fortunes at stud as well where he produced among other good gallopers, Florrie and Philson, each of whom carried O’Brien’s rose and black livery with distinction. Florrie won the 1891 C.J.C. Champagne Stakes in the autumn and in summer of the same year, both the C.J.C. Oaks and Derby; while Philson won the 1893 C.J.C. Canterbury Welcome Stakes.
Mention of Florrie recalls her distinguished dam, Rubina, an early example of O’Brien’s unerring eye for a thoroughbred. He was first attracted to any racehorse by its physicality, rather than its pedigree. If the horse passed the ‘looking-over’ test, the pedigree came later. Of course, not all of the horses he looked over, he bought, but as Mae West once observed: “it’s better to be looked over than overlooked.” Minor physical blemishes never worried O’Brien either, for such faults often rendered the individual in question a bargain. Rubina was a case in point. An Australian-bred filly foaled in 1880, she was by the 1874 A.J.C. Derby winner, Kingsborough, out of an English daughter of Caractacus, the winner of the 1862 English Derby. O’Brien bought her out of a claiming race at Riccarton and then promptly saddled her up to win the very next event. In all, O’Brien trained her to win more than twenty races, and the gallant mare put the seal on her fame by winning the 1885 C.J.C. Great Autumn Handicap over a mile-and-a-half. At stud, she went on to produce not just Florrie for O’Brien but Vandal as well. Afterwards, when at the Wellington Park Stud, she foaled the outstanding Machine Gun.
It was mainly as a result of his winnings with Tasman that in February 1883 Dan O’Brien was able to take over the Racecourse Hotel at Riccarton from a Mr Seabright. The stabling connected with the hotel was first-rate and being so adjacent to the racecourse was to prove a great convenience to Dan, as well as all those visitors having horses in training who temporarily resided there in the years to come. Indeed, the 1880s came to represent O’Brien’s golden epoch on the Turf, and the Racecourse Hotel played an essential part. A team of other good horses followed after Tasman and Rubina during that decade including Trenton, Gipsy King, Sextant, Freedom, Carbine and Loyalty.
We have already met Trenton in this chronicle. Bred by the brothers, Thomas and Samuel Morrin, at their Glen Orchard Stud in Auckland, Trenton was from Musket’s second New Zealand crop. His dam, Frailty, was a particularly well-bred mare and was one of that batch of yearlings brought to Auckland by Mr E. Perkins. Trenton’s racecourse debut came in the Welcome Stakes at the Auckland Racing Club’s 1883 Spring Meeting sporting the colours of the Thames identity, Captain William Fraser. Nine juveniles comprised the field, and no less than six of them were by Musket including the favourites, Woodnymph, a sister to Martini-Henry, and Krupp. Trenton’s win was altogether unexpected, for most of his stable companions beat him in his trials and so little was thought of his chances that Colonel Fraser, who liked to have a bit on, failed to win more than a couple of hats besides the stake. A feature of the race was that Jack Chaafe, the veteran trainer who had served both Justice Cheeke and Andrew Town in New South Wales, trained all three placegetters. A unique feature of Trenton’s two-year-old season is that he raced in different ownership on all three occasions. His second appearance came in the Midsummer Stakes at the Auckland Summer Meeting, this time under the registration of Mr W. Somerville. Again he took the public by surprise when he got up and paid a dividend of £8/14/- on the Totalisator. It was a few days after this meeting that the leading Canterbury sportsman, George Stead, bought Trenton for an undisclosed sum, but rumoured to be £400. Trenton’s third and final race for the season came at the Canterbury Jockey Club’s Autumn Meeting when he won the Champagne Stakes by a length with two others preferred in the betting. It was a few days after this performance that George Stead submitted Trenton along with some of his other horses for auction with Messrs C. Newton and Son in Cashel-street, Christchurch.
The son of Musket was run up to 750 guineas, which Dan O’Brien bid for him, but Stead bought him in at 850 guineas. After another of his horses, Aimee fetched only 25 guineas, Stead withdrew all his other horses from the sale. O’Brien negotiated privately afterwards and secured Trenton for 850 guineas. It was a stiff price at the time, but O’Brien had great faith in the horse. It was a faith sorely tested as Trenton was plagued by leg and feet problems throughout his career. O’Brien backed Trenton heavily for the New Zealand Derby at Canterbury and coupled him in doubles with Tasman and others for the New Zealand Cup in the spring of 1884, but as fate would have it, the horse’s near foreleg filled both above and below the knee and he didn’t start again that year. O’Brien did manage to get him to Dunedin racecourse twice in the late summer and autumn of 1884 where he ran second in the Dunedin Cup and won the Challenge Stakes. Long before, O’Brien had made a tryst with destiny and had promised himself that when the right horse came along, he would return to Melbourne, the city of his birth, and try for the Melbourne Cup. Now, in possession of Trenton, the time had come for redeeming the pledge. O’Brien set the horse for a good old-fashioned betting plunge in the 1885 running of the Cup. New Zealanders are remarkably loyal to their horses when they travel abroad, and to a man, they were particularly sanguine about this one. Purportedly the best galloper in the Shaky Isles, the chortling could almost be heard from across the Tasman when Trenton was handicapped at only 7 st. 13lb in Australia’s richest race.
Trenton opened his Australian account in the Melbourne Stakes, easily defeating Sheet Anchor and the best Australia could offer. After this, his jockey Alec Robertson stood him out for a lot of money, investing no less than £1,100 of his own, which, with presents, would have returned the ill-fated rider nearly £15,000 – had he got home. How unlucky Dan was on that Tuesday! A huge field of thirty-five lined up for the Cup that year. Trenton was a very lazy horse that required no end of riding. Although passing the abattoirs in the Cup Trenton was in a forward position, it was there that Robertson dropped his whip. Perhaps never before has more money been offered for a whip up the length of the Flemington straight but none of Robertson’s fellow postillions obliged. Sheet Anchor, Grace Darling and Trenton finished as one, with only short heads separating them in that order. The time for the race was 3 minutes 29 1/2 seconds – the first time that a Cup winner had cracked 3 minutes 30 seconds. Later in the week, Trenton hinted at the travesty of the result when he won the V.R.C. Royal Park Stakes on Thursday and then bowled over the great Nordenfeldt at weight-for-age in the V.R.C. Canterbury Stakes on the last day of the Flemington Spring Meeting. Trenton set an Australian record for the two-and-a-half miles that day. It was the last time the great horse carried O’Brien’s colours. Returned to Riccarton, O’Brien was getting the bay galloper ready for another tilt at the Melbourne Cup when Sir William Cooper interceded in mid-July 1886 and bought Trenton for an undisclosed sum, but reported to be 2300 guineas. The horse then left O’Brien’s stable and went across to Randwick and Tom Lamond. Considering Trenton’s subsequent career both on the course and at the stud in Australia and England, despite the sum, no one could doubt that old Dan got the worst of that particular transaction.
Dan O’Brien’s next Australian odyssey came courtesy of another son of Musket – and the daddy of them all – in Carbine. Bred at Sylvia Park by the New Zealand Stud Company and offered through the Durham saleyards in Auckland on January 7, 1887, the yearling that was destined to become Australasia’s greatest ever thoroughbred was bought by Lucky Dan for 620 guineas, and at the price, the mealy-bay colt was far from the most expensive Musket sold that year. In repose, there was nothing very striking about him, while his imperfect front legs were a decided detraction on first impressions. Moreover, an indifferent hind action when walking meant he hardly improved upon further acquaintance. But O’Brien saw beyond those fault lines, and it was to his everlasting credit that he did so, for the colt wasn’t made for walking but for running. Appearing five times as a juvenile in New Zealand, he finished the season unbeaten. O’Brien entered him for both the Victoria Derby and Melbourne Cup in 1888, but for all of his juvenile precocity, Carbine wasn’t rated the best of his age by the Melbourne handicapper. Although weighted at 4lb more than weight-for-age for the Cup, it wasn’t enough to trump the Hon James White’s classy filly, Volley – another of Musket’s progeny – who got 9lb more than the scale. But at those weights, it was never O’Brien’s intention to start Carbine for the Cup, and as early as July he very publicly withdrew him, which led most people – bookmakers included – to assume that the colt wasn’t coming across the water at all. But the Victoria Derby remained very much the object of desire that spring for Dan O’Brien, perhaps because Melbourne was the city of his birth. In those days the Derby was a popular medium for speculation, and it was possible to back a candidate for thousands of pounds even months before the race. And thereby hangs a tale.
The Carbine commission was got on even before the colt had left New Zealand. All the big bookmakers were secured but had the purveyors of prices entertained the slightest suspicion that Carbine was half as good as he was, or even that he was coming at all, we can be sure that much less than tens would have been offered against him. Throughout winter, Volley had been a warm favourite at about 4/1 with Lonsdale at fives the only other under double figures. However, when Melos emerged on the scene at the Hawkesbury and Randwick Spring Meetings, he displaced the filly as the pea at an equally short price. The Carbine commission was started the week before the A.J.C. Derby was conducted and continued at the settling over the A.J.C. Spring Meeting, while at the same time a few men got to work in Melbourne. A lot of money was booked down to fives even when a point less was hardly obtainable. Once the money was on, Carbine set out for Sydney, leaving the Shaky Isles on Monday immediately after Melos had taken our Derby but not arriving aboard the steamer, Huaroto, until the following Sunday evening along with O’Brien, groom Vincent and jockey Bob Derrett. The champion colt was quartered for a while at the A.J.C. Hotel with Dan O’Brien in close attendance. He didn’t start in Sydney on that trip; it was merely used as a staging post en route to Melbourne. When the coterie got to the southern capital, their troubles started even before Carbine raced. Feisty and secretive as ever, old Dan objected to William Dargin witnessing the wonder colt doing a working gallop at Caulfield racecourse shortly after his arrival, and words between the two men soon gave way to fisticuffs, with the fracas being splashed across the newspapers of the day.
In commenting upon this little squabble the Canterbury Times remarked: “Most of our contemporaries have had something to say about a little exchange of fisticuffs between Mr D. O’Brien, the late owner of Carbine, and Mr Dargin, a well-known New South Wales sportsman, which took place at Caulfield just before the recent V.R.C. Spring meeting. It appears that Mr O’Brien attempted to escape the scrutiny of the touts by trying Carbine during the small hours of the morning, but Mr Dargin was altogether too smart for the New Zealander. This inquisitive gentleman, whose modesty is never likely to seriously interfere with his acquisition of knowledge, not only obtained a view of the gallop but actually proceeded to make a close inspection of the colt after he pulled up. Under the circumstances, it is not surprising that Mr O’Brien attempted to instil a little sense of decency into the brazen front of the New South Welshman; that he failed is rather the misfortune of Mr Dargin and his associates than of anyone else. The incidents of the maul are of no public interest, but the subject of the dispute is of considerable moment to every owner of racehorses, and we are surprised that our contemporaries -without a single exception, so far as we have seen – should side with Mr Dargin in his implied interference with the business of other people. It is recognised by sportsmen all over the world that watching a trial without the expressed or implied permission of the owner is at least a breach of racing etiquette in this country, and in England, it is made an offence and a very serious one, too, against the written rules of the sport. Mr O’Brien’s remedy was not, perhaps, the wisest that could have been applied, but it was probably the best, and certainly the speediest, and one that will not be very seriously condemned by those who have witnessed the results of appeals to milder and more orthodox means of protection.”
“This question of touting is a difficult one to deal with. The Caulfield racecourse, it seems, is on a public reserve, and on this account (our contemporaries contend) Mr Dargin had a perfect right to see all he could. This is rather a dangerous doctrine, and capable of a broader construction than even the friends of this amateur tout could desire. Our roads and parks are public reserves, but no sane man will exercise the right he may possess under the letter of the law to thrust his head into the window of a private carriage on the one, nor force his presence upon a picnic party in the other. Had Mr Dargin been guilty of either of these impertinences, everyone would have applauded the author of a prompt and effectual correction. It appears to us that his conduct at Caulfield was no more creditable and if he had fared much the worse from the resort to active hostilities, he would have deserved all he received. How is it, some of our readers will ask, that holding these view we publish at certain seasons of the year accounts of the work on the training tracks? Well, in the first place a newspaper has a few more obligations and a little greater liberty than a private individual. Our readers demand certain news which we can legitimately supply, and we supply it. It is, however, the constant care of our representatives to avoid the publication of information which cannot fairly be claimed as public property. We should never think of prying into the details of a private trial, and least of all should we think of claiming as a right the courtesies that are invariably extended to our reporters by owners and trainers in all parts of the country.”
The Victoria Derby that year was looked upon as a match between Carbine and Melos, but on Derby Eve some big money came for Ensign, another of the Hon. James White’s horses to be ridden by Tom Hales. It is history now how a lapse of judgement on the part of Kiwi jockey Bob Derrett when he relaxed and sat up on the horse believing the race to be won, allowed Ensign to nose him out on the post. Derrett panicked when he eyed Ensign coming at him and in an effort to quicken Carbine, inadvertently struck the colt in a tender part of his anatomy. Later at the same meeting Carbine won the weight-for-age Flying Stakes (7f) and the Foal Stakes (10f). Alas, the stakes on those races hardly compensated O’Brien for his Derby betting losses, and he put the colt up for sale. Carbine’s performances at the meeting were enough to convince the Hon. Donald Wallace, M.L.C., and a prominent Victorian sportsman, to give 3000 guineas for the horse. Unlike O’Brien, Wallace was flush with funds at the time, after his own horse Mentor had won the Melbourne Cup, that year called the Centenary Cup in honour of the founding of Australia. To mark the occasion, the Victoria Racing Club had again increased the prize money by adding 3000 sovereigns to the sweepstakes, thus making the race the most valuable handicap in the world at the time. Besides, Wallace had won a fortune in bets on Mentor and was rumoured to have given his winning jockey as much as £2,500. At the time nobody could blame Dan O’Brien for grabbing such a pot of gold, but given Carbine’s subsequent achievements, it was the biggest mistake of his life.
After the Carbine trip, Dan O’Brien became a regular visitor to Australia. As we have seen, in the autumn of 1890 he brought across Gatling and Whimbrel to contest some of the major two-year-old events at Flemington and Randwick. Each horse performed well, but when Old Dan returned to New Zealand, he went without the horses – leaving them to be sold through Tom Clibborn at Fennelly’s Bazaar. While neither colt changed hands at the fall of the hammer, William Gannon created a sensation a few days later when he paid 2000 guineas for Gatling. Although he ran second in the A.J.C. Derby that year, the chestnut colt never won a decent race. Considering that Old Dan had only paid 260 guineas for Gatling as a yearling, it was a nice bit of horsetrading. It was around this time that some journalists on both sides of the Tasman began to refer to him as ‘Lucky Dan”. He maintained the course of his racing fortunes had little to do with luck and much to do with judgement. Despite his Irish antecedents, his motto, which might have been graven on his heart, was “luck is the superstition of the incompetent.”
Shrewd judgement was certainly to the fore in August 1893 when Dan again crossed the Tasman by the steamer Hauroto bringing two horses with him in Loyalty and Launceston. While Launceston, a four-year-old son of Tasman and Rubina, proved a disappointment, Loyalty, a promising three-year-old colt was a revelation. A slashing individual by St George out of Fair Nell, standing a bit over 15.2, he had only cost O’Brien 160 guineas. The stallion St George, a full brother to Chester that never raced, was sent to New Zealand from New South Wales in 1879 and for some years stood at the Middle Park Stud. Fair Nell, the dam of Loyalty, was a half-sister to the great Sir Modred who was so successful in America. Before leaving his homeland, Loyalty had won the rich C.J.C. Challenge Stakes, over which protracted litigation ensued between O’Brien and the Canterbury Jockey Club concerning the proper prize money to be paid for the race. This contretemps revealed another character trait of O’Brien. When he firmly believed he was in the right, he would pursue that right to the very end. Loyalty wasn’t entered for the Derbies, but he campaigned successfully at both the A.J.C. and V.R.C. Spring Meetings. At Randwick on Derby Day, he won the Spring Stakes and later at the meeting the Craven Plate. Taken to Melbourne, on the day that Carnage won the Victoria Derby, Loyalty appropriated the Melbourne Stakes. Later in the week, he also won the V.R.C. Flying Stakes. As was typical of ‘Lucky Dan’, at the close of the Melbourne Spring Meetings he put Loyalty up for sale at Messrs W. C. Yuille and Company but only a bid of 1750 guineas was made for him, and O’Brien wanted more. The following year in New Zealand, Loyalty won the A.R.C. Auckland Plate and the A.R.C. Great Northern Derby.
O’Brien was plying the Tasman so often, and staying in Sydney and Melbourne so long, that he decided to return permanently to Australia. In October 1893 Dan O’Brien purchased Mount Vernon, an imposing brick residence fronting Botany-street, Randwick for £2,050. The land itself enjoyed a frontage of 124 feet to Botany-street and 156 feet to Bradley-street. In February 1894 he commenced building gilt-edged stabling thereby adding eight roomy, loose boxes with saddle, feed, and other rooms attached. Mr Lewis, the architect, was responsible for the stable design – a building of bright red brick, with the white lines, clearly defined and somewhat in the Gothic style, topped by red French roof tiles from Marseilles. A large dome surmounted the main stable building in the centre with movable ‘lights’, so arranged as to draw out all foul and noxious vapours, so common in confined quarters in hot weather.
A staircase led to the first floor and thence an additional climb to the top of the dome. A magnificent view could be obtained on all sides: to the left was Botany Bay and the Heads in the distance; to the right was a splendid view of Centennial Park and the city. However, it was the view directly ahead that made it Dan O’Brien’s eyrie as it afforded a panoramic view of the racecourse. It was quite a lookout tower, and from it, with a good glass, Dan could easily observe everything that occurred on the training track. The racing correspondent for Truth visited the house and stables in April 1894. He wrote: “The house is snugness itself, beautifully furnished, and the walls of the dining room are covered with the counterfeit presentment of many an equine hero of the dear, dead days of the past. Glorious days many of them were for Dan O’Brien.” The pictures included Tambourini, Tasman and Rubina. The Truth correspondent added: “Perhaps the most interesting of all the collection, however, is a photograph of Mr O’Brien’s stables at Riccarton, Christchurch, with all the then occupants in front, conspicuous among them being the mighty Carbine as a yearling.”
Many Dan O’Brien’s best purchases were out of mares that had not particularly distinguished themselves either on the Turf or at the time of his purchase, at stud. O’Brien purchased them as young horses entirely on their shape and breeding. It amounted to skill and judgement, and both qualities were to the fore when he attended the sale of some Neotsfield yearlings in March 1894. One of those on offer was a little fellow by the great New Zealand racehorse, Welcome Jack, out of a daughter of Gildermire, who ran a dead-heat for an English Oaks before Hurtle Fisher imported her into Australia for his Maribyrnong Stud. O’Brien remembered the grand dam from his youthful days at Maribyrnong, and while most of those attending the sales were put off by this youngster’s lack of size and the fact that he was already a gelding, O’Brien took a fancy and for a paltry 35 guineas secured possession. He named the rising two-year-old Bob Ray, after a well-known figure on the New Zealand racing scene. Bob Ray, like Dan O’Brien, had been one of the earliest professional jockeys in the Shaky Isles and Dan had known him from his days on the goldfields circuit. Later Bob Ray became an owner-trainer, and he owned the inaugural winner of the N.Z. Grand National Steeplechase, Medora in 1875, when none other than O’Brien himself partnered the mare. Bob Ray had also been a part-owner and one-time trainer of Welcome Jack during his racing days and was then living in Australia. So, for a number of reasons, the name seemed most suitable. However, just what Bob himself thought of an emasculated gelding bearing his name, is by no means clear.
Nobody knew much about Bob Ray the first time he appeared on a racecourse; the race chosen was a two-year-old stakes event at the Tattersall’s Club Meeting in September 1894. The knowledgeable ones got 8 to 1 to their money and plenty of it. Although only small, Bob Ray was powerfully built, and he won easily from a big field; O’Brien then took the gelding to Melbourne for the V.R.C. Spring Meeting but the company was a bit hot for him in the Maribyrnong Plate and Flemington Stakes in which he was unplaced. Bob Ray then appeared at the A.J.C. Summer Meeting to run second in the December Stakes to Georgic, a filly that Henry White later raced successfully in England, winning the valuable Prince Edward Handicap as well as carrying off the Cambridgeshire. But it was really at the A.J.C. Autumn Meeting that Dan O’Brien’s powerful little gelding came right into his own. The liberally endowed Champagne Stakes that year only attracted five runners and was looked upon as a testimonial for the crack Victorian youngster, Wallace, whom bookmakers sent to the post at 5/4. Wallace, a son of Carbine, bred and owned by W. R. Wilson at his St Albans Stud, was named after Carbine’s owner, the same Donald Wallace that had bought Carbine from Dan O’Brien a few years before. Under leaden skies, Bob Ray upset the odds although he only got home by a long head from the public fancy, who fought on doggedly after Bob Ray seemed to be cantering at the furlong post. Bob Ray then placed the seal on his merit when, later at the meeting and despite a 7lb penalty, he carried off the Seventh Biennial Stakes (6f) easily in quick time. Dan O’Brien then put the gelding away until Derby Day.
The Derby field that year was a decidedly lacklustre affair on paper and given the failure to nominate Wallace for the race, the assembled cast seemed a bit like a production of Hamlet minus the Prince of Denmark. Favourite for the race was Form; a chestnut son of Cranbrook raced by Henry White, a younger brother of the Hon. James White, and trained by John Allsop. Form owed his market pre-eminence to a brilliant gallop at Randwick on the previous Tuesday rather than anything that he had shown in his races. As a two-year-old, he had finished unplaced behind Bob Ray in the two races at the A.J.C. Autumn Meeting before being taken to Queensland for the Sires’ Produce Stakes at Eagle Farm, in which he spread-eagled the field. His only appearance at three had been an unplaced run in the weight-for-age Hampden Stakes at the Tattersall’s Meeting. The second fancy in the classic was Toreador, carrying the colours of Samuel Hordern. Out of the good producing Kirkham matron, Tempe, Toreador was a brother to Titan and Trieste and had cost his owner 775 guineas. He was only produced late in his juvenile season, when unplaced in two races, but had scrambled in to win the H.R.C. Clarendon Handicap at his most recent start. Mannlicher, the New Zealand representative of George Stead, followed Bob Ray on the third line of betting for the Derby. Mannlicher was unbeaten having won the Champagne Stakes and Challenge Stakes at the Canterbury Jockey Club Autumn Meeting at his only starts at two, and the Derby marked his seasonal reappearance. An impressive colt, Mannlicher was out of a V.R.C. Oaks winner and was a younger brother of Blue Fire, the champion filly of her year who had won the Oaks and Derby Stakes at Canterbury, New Zealand. George Stead had come across the Tasman to watch his prize colt run. Victoria was represented in the race by Onward, of whom James Scobie rather asked much as a juvenile when the horse was unplaced in no fewer than fourteen starts.
The 1895 A.J.C. Derby field and race conditions are set out in the table below:
Derby Day dawned in unclouded splendour and was rather unseasonably warm, causing a number of the horses in the classic to sweat freely even before the flag had fallen. None more so than Bob Ray and his excitability caused some delay at the post before Mr Watson could give his signal. It was the first Derby where owners and trainers of the horses engaged, were not permitted to go on to the course proper before the race, the committee issuing a minute the previous November debarring the practice. Mannlicher set the pace and led Form out of the straight with Bob Ray back running last with Flintlock, although the field was rather well compacted. Bob Ray fought for his head early but was eventually induced to settle. Ernie Huxley laid out a good course for himself that day on Dan O’Brien’s gelding and was happy for Mannlicher to pilot the field for most of the running. The New Zealand colt still held a slight advantage when the field turned for home, with Bob Ray by then about four lengths in arrears. Huxley brought the son of Welcome Jack with a run inside the distance and without ever fully extending his charge, won going away in the final half-furlong. Upon returning to scale, the winner was roundly applauded as Lady Darley, wife of the Lieutenant Governor, decorated him with the blue riband. The Derby that year wasn’t worth much more than half the sum offered for the Epsom, run on the same card, but O’Brien had supplemented the prize with some well-placed bets.
I have already touched on Bob Ray’s breeding, but perhaps a little more might be said. His sire, Welcome Jack, was easily the best horse that Traducer ever got at stud. Welcome Jack was one of the great champions of the New Zealand Turf in the nineteenth century and enjoyed a most distinguished three-year-old season when he won the Canterbury Jockey Club Handicap, the C.J.C. Great Autumn Handicap, Au.R.C. Great Northern Derby, and Auckland Cup among other races. As an older horse, he twice won the C.J.C. Canterbury Cup among other rich events. Gage d’Amour, the dam of Bob Ray, had been a speedy mare by Grandmaster, but once put to stud duties by Henry Dangar at Neotsfield, she became an absolute virago in the paddock when suckling Bob Ray, bullying every mare around. But she threw her weight around once too often, and one morning was found dead near one of those beautiful Neotsfield plantations with poor little Bob standing over her and looking forlorn. One or more of the other mares had kicked her to death. The future Derby winner was thus an orphan at just two months old. Nonetheless, the stud groom ensured the little fellow got his share of milk and human kindness and in due course he came up for sale with the other Neotsfield yearlings. An August foal, Bob Ray was the cheapest of the three youngsters by Welcome Jack offered by Dangar that year.
Bob Ray’s fall from grace after his Derby laurels was as dramatic as it was unexpected. Either during the Derby or on the way home to the Mount Vernon stables after it, the horse smashed a small bone in his knee and was struck out of the remainder of his three-year-old engagements. He missed all of his four-year-old-season as well. After this lengthy furlough, which he spent in the paddocks at Ellengerah on the Macquarie River, old Dan brought him back to work in late 1897, but he failed to show sufficient dash in his gallops. O’Brien then put the gelding up for sale in January at Chisholm’s Newmarket yards but declined to part with him for less than £100 and decided to persevere a bit longer. He did get him to the course once that autumn, but the five-year-old failed to flatter and was sold shortly after the Randwick Autumn Meeting. After a couple of more failures in Sydney, Bob Ray eventually went to race in Queensland where he enjoyed some success sporting the colours of E. G. Blume, including six wins on the reel at the Rockhampton Tattersall’s and Spring Meetings in 1899.
Given that Bob Ray was hors de combat for the balance of his three-year-old season, the course was cleared in the remaining classics for the colt that he had upset so spectacularly to win the Champagne Stakes the previous season, Wallace. Wallace was the finest animal sired by Carbine in his four seasons at stud in Australia, and 1895 was a fateful year for the horse, his owner and breeder, W. R. Wilson, and the stud where Wallace was bred, St Albans at Geelong, Victoria. Wallace was one of the very first of Carbine’s foals in the stallion’s first season at stud and was out of Melodious, a sister to Melos. The colt had created something of a sensation when he won the weight-for-age Flying Plate against older horses during the 1894 V.R.C. Spring Meeting and before his fateful clash with Bob Ray in the Champagne Stakes, had been started for the Doncaster Handicap only two days earlier. Wallace had not been entered for the A.J.C. Derby, and indeed his entire spring campaign that year had been uncertain because of the announcement in early March of the intention of his owner, W. R. Wilson, to retire from the Turf and thus dispose of his extensive holdings including the famous St Albans stud and stables together with all of his horses.
At the time, St Albans was the most famous stud in the southern hemisphere and though it failed to produce a winner of the A.J.C. Derby during the height of its fame, its influence on Australian bloodstock had been profound. W. R. Wilson had acquired the property in 1890 for £70,000 and had then set about restocking the stud, outlaying a further £30,000. By 1895 however, the economic recession was taking its toll on racing with the V.R.C. slashing prize money, and yearling prices plummeting. This together with other financial pressures prompted the Master of St Albans to liquidate the enterprise, choosing the novel concept of a lottery to dispose of the estate and its horseflesh. There were 125,000 tickets of £1 each with 130 prizes. Wallace, then a crack two-year-old, was listed as the ninth prize in descending order of value with the lottery draw taking place in the Centennial Hall, Brisbane, by George Adams one week before the Melbourne Cup. Doubtless, with the wisdom of foresight, Wallace, given his remarkable three-year-old season, and even more remarkable career at stud, should have topped the prize list. A syndicate of four people from Creswick won the colt, and W. R. Wilson promptly renegotiated a buyback for £2,500 plus winning contingencies, as he did with a number of other prizes including the estate itself for just £24,000. The engagements at the V.R.C. Spring Meeting of Wallace and other racehorses involved in the lottery had stood during the course of the draw and its aftermath. Thus Wallace, who had earlier in the season won the Caulfield Guineas effortlessly before being raffled, proceeded on his glorious way to winning the Victoria Derby, C.B. Fisher Plate, Champion Stakes, A.J.C. St Leger, Sydney Cup and the Cumberland Stakes in a magnificent season. As a four-year-old Wallace failed to stand a preparation and after just one appearance was retired to stud.
The domination of Wallace that season was such that none of the horses that ran in the 1895 A.J.C. Derby ever won a principal race afterwards. However, I should mention that Form, whom Henry White bred at his Havilah Stud, later won good races in England, including the Westmoreland Plate, carrying his breeder’s colours. Mr F. W. Day trained Form in the Old Country. Henry White, like his older brother James, was determined to crack the English racing scene and he did enjoy a fair measure of success there over the years, not just with Form but more particularly, Paris, and Georgic. Like his brother, he mated mares with Australian stallions to English time, but he had no more luck in winning an English classic with such a deliberate policy than did James himself.
Along with Bob Ray, Dan O’Brien decided to sell his fashionable Mount Vernon residence and stables and move back to Riccarton in New Zealand. Although the establishment was passed in at £2,800 when first submitted for sale by Messrs Richardson and Wrench, O’Brien eventually let the place to John Gough, who at the time had a fairly large string of horses in work at Randwick. But it wasn’t the last that Australia saw of this peripatetic adventurer from across the Tasman. In January 1908 O’Brien decided to return to live in Sydney, selling out of the Hotel Criterion in New Plymouth, N.Z., and buying the Hotel Victoria in George Street. But O’Brien hadn’t just come here for the ambience of Sydney hotel life. He had also arranged for Maranui, a horse he bred and owned in New Zealand to relocate here as well. Not a particularly well-performed galloper – he had failed in the A.J.C. Derby the year before – O’Brien managed to get him into the Caulfield Cup with just 7 st. 11lb and had backed him for the big spring races even before he had left New Zealand.
Why didn’t it come as a surprise when Maranui, after the Cups weights had been declared, fared much better at the A.J.C. Spring Meeting than hitherto disclosed form suggested he was capable? The horse managed to run third in both the Spring Stakes and The Metropolitan. Meanwhile, O’Brien had helped himself freely to some long-priced wagers about his charge in the Caulfield Cup, which that year was particularly weak. When race day came around, Maranui had shortened in the betting to be the second favourite, and he had the Cup in his keeping a long way from home. Bookmakers were again reminded – as if they should have needed it – that the passing of the years hadn’t diminished the genius of ‘Lucky Dan’ O’Brien for planning a plunge. But for going lame a few days after the Caulfield race, Maranui may well have avenged Trenton’s narrow defeat in the Melbourne Cup twenty-three years earlier. O’Brien had purchased Grafin, the dam of Maranui, at the dispersal sale of Donald Wallace’s Lerderderg Stud in March 1895. She was by Carbine and thus in some small measure assuaged O’Brien for peremptorily parting with his former champion.
Maranui’s victory ensured that no mortgage remained on the Hotel Victoria, located between Hunter and Wynyard Streets, and one of the foremost public houses in the Sydney of the day. O’Brien decorated the walls of the new premises with photographs and mementoes celebrating his glory days on the Turf. Pride of place in the smoking room under a painting of Carbine was the framed agent’s receipt for the 620 guineas O’Brien had paid to secure the great son of Musket when he was sold as a yearling by the New Zealand Stud Company. Later on, in 1910 O’Brien was also the licensee of the Crown Hotel on the corner of Crown and Cleveland Streets. On many a cold winter’s night, in front of a crackling log fire and warmed by a glass of ale, mine host would regale especially favoured patrons with his tales of derring-do on the Turf. Dan O’Brien ended his days in Sydney, and died at Lewisham Hospital, in August 1916 after a very lengthy and painful illness, leaving a widow and a daughter. He had been operated on for cancer in the jaw, repeatedly, but the malignant roots had got into the tissues of his throat, and the knife proved unavailing though it did prolong his life for a time. He was sixty-eight, and his remains were interred in Waverley Cemetery. Dan O’Brien had retained his love of racing and boxing to the very end. His last good winner had been with a horse of his own breeding when Respect won the 1910 Gimcrack Stakes at Randwick. Tom Willis (‘Milroy’ of the Sydney Mail) once discussed writing O’Brien’s life with him, but the idea was scuttled by a publisher wanting the cream of any profits. More is the pity, as it would have been an invaluable addition to the literature on Australian and New Zealand Turf lore of the late nineteenth century.