Kings of the Turf

A History of the AJC Derby From 1861 to 1980

1877 – The Defeat of Chester!

1877 was remarkable for the presence of two very high-class racehorses – each amongst the best gallopers to race in Australia in the nineteenth century – in Chester and First King.  At that time in Australia’s history, nothing added spice to the game of racing more than a dash of inter-colonial rivalry conducted across the banks of the Murray River.  Given that Chester hailed from N.S.W. while First King came from Victoria, opinions on the merits of each colt varied markedly according to geography.  The two colts each happened to make their racing debut on New Year’s Day, albeit one at Randwick and the other at Flemington.


Chester (Racehorses in Australia)

Chester was a fine big raking son of Yattendon from the imported English mare Lady Chester, a daughter of Stockwell.  Bred and initially raced by Edward Cox of Fernhill, he was a dark bay or brown colt standing nearly 16 hands, with proportionate power all around, albeit offset by a rather plain head.  Etienne de Mestre, who was then only in his mid-forties, and beginning to cast a giant shadow across the Australian Turf, trained Chester at Terrara in the Shoalhaven district of NSW.  Although Chester was beaten a head upon debut by Viscount, a horse raced by Sir Hercules Robinson, Chester created a big impression.  The Stockwell blood was legendary, and considering the colt’s size and scope, astute racing men concluded that he merely needed time to furnish into the best horse in the land.  The NSW Governor, Sir Hercules Robinson, ruefully came to the same conclusion, despite Viscount’s victory.  The irony was that Robinson had been offered Chester as a yearling upon his own terms, but His Excellency had thought little of the son of Yattendon at the time.

Etienne de Mestre, Phoebe Rowe & Clara Rowe c1854 (The Master’s Touch)

If Chester beguiled the Sydney racing public, then First King no less bewitched their Melbourne brethren.  The first son of King of the Ring to appear on a racecourse, this homebred from the St Albans stable of James Wilson was a half-brother to the former champion two and three-year-old filly, Maid of All Work.  A larger edition of his sire, First King brought with him from St Albans a reputation as the best youngster ever trained at that notable establishment and was duly supported into odds-on. He won effortlessly on debut.  He followed it up by taking the Barwon Plate at Geelong.  Alas, any clash with Chester was not destined to occur until the Victoria Derby as James Wilson had not nominated First King for any of the two or three-year-old classics at Randwick, and Chester wasn’t slated amongst de Mestre’s team to represent Terrara at the autumn gathering at Flemington.  The absence of any reward to the breeder of the Sires’ Produce Stakes’ winner at either Flemington or Randwick in those days, often led them failing to nominate stallions, and the races becoming less competitive as a result.


First King (Racehorses in Australia)

In Chester’s absence, First King’s unbeaten juvenile season on the Turf culminated with a victory in the Ascot Vale Stakes, despite the added impost of a 5lb penalty.  In turn, First King’s absence enabled Chester to rout the opposition at the Randwick Autumn Meeting when he snaffled in quick succession the Champagne Stakes, Breeders’ Plate and Sires’ Produce Stakes, netting his lucky breeder/owner £1770 in stakes.  So impressive was Chester during that week that the Hon. James White, who was just then beginning his extraordinarily rich foray into thoroughbred ownership, offered Edward Cox the princely sum of 2000 guineas in exchange for the wonder colt. It was an offer that Cox could not refuse.  Indeed, so taken was White with the pedigree that during the same week at Messrs Clibborn and Company’s annual sale of yearlings, he also paid 1150 guineas to Cox for Chester’s full brother, the appropriately named Roodee, then the highest price ever given for a yearling in Australia.

Despite rumours to the contrary following the sale, Chester remained in the stables of de Mestre, and both he and Roodee were despatched by special steamer to Terrara to be prepared for the spring.  No sooner had the autumn meeting concluded at headquarters, than bookmakers installed Chester as short as 7/2 for the Derby.  As good as he looked, however, when the Melbourne Cup weights came out in mid-June the V.R.C. handicapper rated First King as the best two-year-old of the season with 7 st. 1lb, while Chester was rated 3lb inferior on 6 st. 12lb.  Whatever the handicapper may have thought, associates of the Terrara stable soon busied themselves in heavily supporting Chester for the rich spring plums – and not just the A.J.C. Derby, but the Victoria Derby – Melbourne Cup double as well.


The 1877 A.J.C. Derby field and race conditions appear in the table below:


Ten horses were declared for the A.J.C. Derby.  Chester’s jockey in the race was George Donnelly, an associate of the de Mestre stable for some seasons but at thirty-four-years of age, was nearing the end of his active life in the saddle.  Donnelly had successfully partnered Chester in the autumn and often acted as travelling foreman for the Terrara operation as well as the stable rider.  Donnelly’s duties didn’t end there as he often took charge of the horses when they first arrived at Randwick or Flemington for their engagements, in the weeks before de Mestre himself journeyed from the Shoalhaven.

Donnelly had ridden Tim Whiffler and Dagworth in most of their races, and the ill-fated Robin Hood on the occasions of the Victoria Derby and AJC St Leger for de Mestre.  In the late 1870s, there were far fewer race meetings held, and in taking the mount on Chester, Donnelly had done little or no race riding since the previous Randwick fixture.  As a result, during the winter months, Donnelly had put on considerable weight. When he belatedly learned that despite the change in Chester’s ownership he was still to retain the mount, Donnelly had to strip the more than half a stone from his frame in the course of little more than a week or so.  It left him in a somewhat weakened state and unable to do full justice to Chester, particularly in the dramatic last furlong of that memorable Derby.

Heavy rain had fallen at Randwick in the week preceding the opening of the A.J.C. Spring Meeting that year and a soft track awaited the ten that confronted Mr Want’s flag.  Chester had retained his hold on the public’s imagination right to the death, while the best-backed horse to beat him was Woodlands.  A son of Maribyrnong, Woodlands failed to attract the judge’s attention in his only two juvenile outings but had emerged as a genuine contender by winning the Maiden Plate and Hawkesbury Guineas at the Clarendon course upon resumption.  The only other colt under double figures was the sole Victorian challenger, Salisbury, trained by Bob Sevior at Flemington.  It was disappointing that more horses from Melbourne hadn’t ventured north but the fact that the railway on the NSW side didn’t extend to Albury, and the risks inherent in a voyage by sea rendered the journey quite difficult.  De Mestre’s stable had a useful second string to its bow in Cap-a-Pie, a minor place-getter in the Sires’ Produce Stakes in the autumn on the same course. Andrew Loder started two representatives in the race, Black Eagle and The Dean, both sons of Yattendon; with Black Eagle the more fancied of the pair on the strength of his second in the Hawkesbury Guineas.  Michael Fennelly’s stable hope was the long-priced, roguish Ingomar, while Byron Lodge started Amendment.

In cold and miserable weather, the horses were walked to the Derby start in blankets with the jockeys following on foot.  After an even start, Salisbury, drawn on the extreme outside, promptly took up the running, a role that he fulfilled for the first ten furlongs of the trip and which for much of the time he was pulling his jockey out of the saddle.  Meanwhile, Donnelly held Chester in a good position on the outside.  As the field climbed the hill at the back of the course, the lead of the Victorian representative was considerably reduced and as the field tightened Cap-a-Pie cannoned into Amendment, costing that horse three or four lengths.  After Salisbury compounded passing the ten furlongs post, Chester and Cap-a-Pie raced towards the lead with Woodlands challenging on the extreme outside and joining the Terrara pair at the Leger.  In an exciting last furlong, the race remained in doubt until the last stride when Woodlands just managed to prevail.  The finish was so close, however, that several telegrams announcing Chester’s success were despatched from the course before the judge hoisted the number 6, much to the relief of the fielders.  No sooner had the result been announced, than the public recriminations against Donnelly’s inept handling of the favourite began.  It was just about the last mount that the hapless Donnelly ever accepted in a race.  Never reckless with his earnings, he later became the licensee of the A.J.C. Hotel at Randwick, and for a few years quite successfully trained a small team of horses on the side.


The winner of the Derby was a dark brown colt standing about 15.1 hands, a son of the wonderful stallion Maribyrnong from the good producing mare, The Alpaca.  Mr Thomas Lee had bred him at Bathurst, and Joe Burton had broken-in the colt.  The Alpaca was a mare by Kingston from Lilla, the dam of the 1871 Derby winner Javelin, and Commodore, winner of the 1873 St Leger at Randwick.  Thus, in victory Woodlands had proved himself a worthy scion of a classic-winning family.  The Alpaca belonged to a very old Lee-breed and descended from a mare that was supposed to have been bred at Camden Park and was said to have been thoroughbred.  Bought from his breeder as a youngster by the well-known Sydney bookmaker, Joe Silberberg, Woodlands had already passed through the hands of two trainers before entering the Sydney stables of Joe Cook.  James Wilson, the master of St Albans, prepared Woodlands for his racecourse debut in the Maribyrnong Plate in which he ran badly.  A dispute then saw the colt transferred to Sevior’s Flemington establishment, although without any marked change in his racing fortunes, for at his next appearance he proceeded to get lost in the Champagne Stakes at Randwick won by Chester.  It was after that autumn meeting that Silberberg decided to leave the colt in Sydney to be trained by Joe Cook. Silberberg won a poultice on the result; he was a tremendous gambler who had risen from the ranks and climbed into money rapidly, and no one but a desperate speculator would have risked a parcel of money on any colt to beat Chester that day.

For Cook the Derby represented his first important training success; he had begun stable life as a headman for Tom Lamond at Waterloo soon after Lamond moved to Sydney in the early 1870s.  In fact, it was only a short while before Woodlands’ Derby that Cook had even decided to strike out on his own and the manner in which he produced the son of Maribyrnong at both Hawkesbury and Randwick suggested a promising career was in store.  Never overseeing a large string, Cook in the years that followed made a name for himself from his Waterloo stables.  Apart from Woodlands, his best horse was arguably Little Bernie with whom he won both a Metropolitan and a Summer Cup in the early nineties.  Cook was the first of three successive generations of the family to win big staying races at Randwick.  His son Joe junior owned and trained Amounis at the very start of his career and a little later won a Sydney Cup with Winalot.  Joe junior’s son, Clyde Cook, was to prepare Persian Lyric to win the 1960 A.J.C. Derby, while Clyde’s daughter married the high-profile race broadcaster, Ken Howard.


The subsequent form of the Derby colts on the remaining three days of that 1877 A.J.C. spring fixture suggested that it was a quality year for three-year-olds.  On the second day of the meeting, Amendment won the Great Metropolitan Stakes while Woodlands made it four wins in a row when he took out the Maiden Stakes.  On the third day, Chester – with the rising young jockey Paddy Pigott replacing Donnelly in the irons – got his revenge on Woodlands when he comfortably won the Mares’ Produce Stakes (10f).  It was then on to Melbourne and that much-awaited clash with First King.


De Mestre arrived in Melbourne in late September with Chester and five other horses, stabling them initially in boxes at the Racecourse Hotel at Flemington before venturing out to Williamstown where the horse did his final gallops away from the general body of touts.  The Terrara stable had learnt the lesson of matching an unfit jockey with a very fit horse and Piggott had been retained for all of Chester’s Melbourne engagements.  Woodlands arrived in Melbourne about a week after Chester, and Joe Silberberg made no secret of the fact that he wasn’t anxious to try his luck against either the Hon. James White’s putative champion or Melbourne’s wonder colt in the Victoria Derby.  Silberberg had backed Woodlands heavily for the Melbourne Cup and preferred his chances in that race at the weights, given that his colt received 19lb from Chester and even 3lb more from First King.  As it turned out, Woodlands almost missed the entire Flemington meeting when he was the subject of a bungled nobbling attempt on the previous Saturday evening. Malefactors managed to open the window of his box and throw half a beer bottle, jagged-edged, as well as several large oyster shells onto the floor in a bid to inflict injuries if the colt happened to tread or roll on the objects.  But apart from a few scratches on his quarters, he emerged unscathed.

There were also disquieting rumours concerning the well being of First King out at St Albans, although given the absolute secrecy that surrounded the workings of that stable nobody could be sure.  The truth was, however, that a split hoof had severely interrupted First King’s Victoria Derby preparation.  The problem compelled him to run in plates while Chester ran barefoot in what proved a hollow victory for the Sydney colt in a time that was the fastest on record.  On the same programme, Woodlands ran a good second for the Melbourne Stakes against the older horses at weight-for-age.  The Derby result, in particular, had considerable influence on Cup betting and Chester was elevated to equal favouritism with Savanaka, the three-year-old grey colt that had been the subject of a sensational betting plunge by the St Albans confederacy.

Owned by the V.R.C. committeeman and steward, Herbert Power, Savanaka was a brother to Lecturer and Kingsborough – yet unlike either of that pair, he was a narrow and weedy type.  James Wilson very early on concluded the horse wasn’t up to Derby weight but would be well suited in the Melbourne Cup under handicap conditions. His entire racing programme had been calculated to getting this son of Kingston into the 1877 Cup with nothing on his back; he had only raced twice as a two-year-old, finishing unplaced in the Maribyrnong Plate and then, later at the same meeting, showing he could gallop by taking out the Flying Stakes.  Within a matter of days of the Cup weights being declared, Savanaka had been backed to win over £40,000, and the bulk of the money was taken within just a few minutes on a June Saturday evening at Tattersall’s in Melbourne.

With so much money at stake, it was hardly surprising that the Melbourne Cup that year proved such a dirty business.  The public had followed the St Albans stable lead in the betting ring supporting the colt into 5/1 equal favouritism with Chester and would have gambled more had they known that Wilson had tried the horse to beat Don Juan’s Cup record time on his private training track by fully three seconds.  Chester brought the plunge unstuck, but only just – and not before a Cup brimful of incidents.  The course remained greasy after the rain, and de Mestre elected to run Chester again without plates, although on this occasion he took the precaution of having a few nails hammered into the hooves to prevent the colt from slipping.

Thirty-three horses faced the starter, and Chester won rather cleverly at the end, although the margin of a half-head over Savanaka could have been so much more, had Pigott not left off riding when he thought the race was won.  Nonetheless, Savanaka was desperately unlucky, having suffered interference when a horse fell back on him sharply after passing the sheds and a stride past the winning post he was in front.  Woodlands ran well to the distance but then dropped out of it.  In winning, Chester became only the third horse – after Lantern and Briseis – to take the Derby/Cup double, although in Lantern’s year it should be borne in mind that the Derby was run after the Cup.  Owner James White wasn’t present for the running of either race.

The press was not averse to giving the St Albans stable some criticism for the secrecy and plotting behind the Savanaka coup. The Australasian summed up the general mood when it commented: “Certain we are that with the general public there is a feeling of intense satisfaction that the clever party at St Albans, whose deeds are dark and ways mysterious, got bowled over for once, and that de Mestre won the Cup for a man who races for sport, not money.”  Herbert Power bridled at this sort of criticism, replying in a letter to the same paper that St Albans “is not a lounge for touts and sporting correspondents – an advantage I hope it may continue to have for many years to come.”  Of course, Power wasn’t to know it at the time, but a small measure of revenge would be extracted when Savanaka, in receipt of 12lb, later beat his Melbourne Cup conqueror in the 1879 Sydney Cup, landing a more modest plunge in so doing.

The fall-out over the failed Melbourne Cup plunge on Savanaka tended to deflect attention at the time from the successful one landed on Chester.  For never in the annals of the Australian Turf had there been such heavy settling for a V.R.C. Spring Meeting, and the fact that the bookmakers’ obligations were met so promptly said something about the resources of the Melbourne ring.  Long before noon on the following Monday, a large crowd had assembled ‘under the verandah’ in Collins-street. One of the first transactions to be settled was the payment by Joe Thompson of £10,000 in banknotes to Septimus Stephen, the representative of James White, who had taken £10,000 to £400 about Chester for the Cup. Within an hour Thompson had paid out between £20,000 and £30,000 while others of his brethren had parted with big money as well.  In collecting such a large sum, Septimus Stephen had taken the sensible precaution of taking along Jem Mace, the famous prize-fighter, to act as a bodyguard.

After the Cup meeting, Chester was not brought back to Sydney but was left at Williamstown to be prepared for the Champion Stakes, for which he was made an even-money favourite.  That race, in early January, held out the promise of a return clash with First King.  By then First King’s split hoof had healed, and James Wilson was able to give his charge the requisite amount of track work.  It was on the strength of First King running three miles at St Albans in a very smart time on the tan, that James Wilson accepted £3,000 to £500 about him for the Champion Race, declaring to his close friends that neither Chester nor any other horse could beat him.

In the trial, it was rumoured that he had conceded 28lb to Savanaka and beat him with consummate ease.  Wilson’s confidence was well based, as First King’s time in winning the Champion Race by four lengths from Chester was 8 ½ seconds faster than three miles had ever been covered anywhere in Australia. It was such that the V.R.C. Secretary, Mr Bagot, ordered the Flemington course to be re-surveyed only for it to be found to be one link more than the official figure.  While Chester was matching strides with First King in the Champion Race, Woodlands was winning the Maiden Plate at the Hawkesbury Midsummer Meeting.  It seemed an appropriate reflection on the way their respective careers had progressed since that fateful Derby Day at Randwick.


First King’s dominance over Chester continued in the V.R.C. St Leger two months later, with a victory by a short head after a cracking race in which the only other starter was Pardon, a stablemate of First King, who had been entered by James Wilson as a pacemaker.  Nonetheless, many maintained that the verdict would have gone the other way had Pigott waited longer.  A few days later with no Chester, First King claimed the Australian Cup as well.  Arguably it was the hard run in the Cup that led to Chester easily upsetting the St Albans’ crack in the Town Plate (2m) on the last day of that V.R.C. Meeting, although the 7lb penalty the Champion Stakes winner was required to carry didn’t help matters.  After his tough campaign, First King wasn’t part of the St Albans’ assault on the Randwick Autumn Meeting.

De Mestre wasn’t hard on Chester once he got the colt back to Sydney to be freshened-up for the St. Leger at Randwick.  Albert Cornwell whispered to his close friends that Cap-a-Pie, whom he had taken over from de Mestre to train on behalf of Andrew Town, would beat Chester in the race if de Mestre persisted with his laid-back approach.  And so it proved – in a race in which the Derby winner, Woodlands, ran last. Handicapped with 8 st. 9lb for the Sydney Cup, James White didn’t allow Chester to take his place but chose to rely instead on Democrat, a lightweight with 6 st. 5lb and a comparative outsider.  In winning the race, Democrat capped a remarkable few months for White.

Chester instead was held over to match strides again with Cap-a-Pie in the Cumberland Stakes, and the men from Richmond put their money down for another upset but the St Leger gallop had stirred Chester up, and he managed to collar Cap-a-Pie on the line to make a dead-heat of it.   A run-off was demanded, and Chester was kept moving about until they went to the post, and in the re-run, James White’s representative reigned supreme.  He showed just what a cast-iron customer he was on the fourth day of that autumn meeting when he again ran over the same horse in the three-mile A.J.C. Plate to complete his three-year-old season.

Chester’s string of victories saw the colt finish the season as the highest stakes winner, although his tally was about £1,000 below Richmond’s three-year-old haul.  In so doing, Chester ensured Yattendon topped the winning stallions’ list and promoted James White to become the leading owner for the season in Australia for the first time.  White won the title with five individual winners of nineteen races and began a dominance that was to last over a decade.  In winning this first title, White relegated his own trainer, Etienne de Mestre, into second place on the owners’ list.


Chester’s subsequent career was largely restricted to the best weight-for-age races run at Randwick and Flemington, in which he was invariably difficult to beat, although he did run unplaced as top-weight in both the 1878 and 1880 Melbourne Cups- two of the only three occasions that the great horse finished unplaced.  It was in that 1878 Melbourne Cup won by his stablemate Calamia, that Chester ran into a post leaving his jockey Joe Morrison with a badly broken leg that slowed, and eventually, ended his riding career.  Morrison was never the same after that, often requiring a walking stick to get around.  It was after the incident with Chester that the V.R.C. took steps to rail in the entire Flemington course.

After that Cup crash Chester was given a spell, and when he came back into work didn’t return to Terrara but went instead into the stables of Michael Fennelly, James White’s key retainer in the training ranks. Fennelly was to enjoy a remarkable success with White’s team in a relatively short career, and Chester proved no exception for he managed to rekindle the big horse’s spirit to again prove dominant in the weight-for-age ranks.  It was in that first campaign for Fennelly – at the 1879 A.J.C. Autumn Meeting – that Savanaka eventually got his revenge on Chester for that famous Melbourne Cup loss when he easily beat the crack in the Sydney Cup when in receipt of 12lb.

Intermittent lameness was to mar his last season on the Turf and in his last important win – in the 1880 Melbourne Stakes – he arrived in the paddock with his legs swathed in bandages, only for the bandages to come off in the race itself; he won by a neck and walked tenderly afterwards. Chester was eventually retired to the stud for the 1881 breeding season after a career of 30 starts resulting in 19 wins, 7 seconds, and one third for winnings of £7,887 and his victories ranged over distances from five furlongs to three miles.  James White installed Chester as the foundation stallion at what would become Kirkham Stud, at Narellan, near Camden, which in the early 1880s he began to develop as a thoroughbred nursery.

Chester (Graham Caves Collection)

The triumphant story of that enterprise will be left to later pages but let me observe here that Chester got a host of winners from the well-bred English mares that White imported there.  The best unquestionably was the mighty Abercorn, but other good colts included the likes of Camoola and Stromboli, while rarely did a season go by when he didn’t have a brilliant juvenile to represent him as the likes of Titan, Acme, Autonomy and Uralla attest.  Chester died at Kirkham in November 1891 as a result of peritonitis, causing a rupture of the stomach and diaphragm.  An impressive memorial stone still stands at Kirkham proclaiming that Chester lies buried underneath.


Chester’s Grave At Kirkham c. 1900


Before leaving this chapter, permit me a word on Woodlands.  Although much inferior to Chester and regarded as a lucky Derby winner, Woodlands was nonetheless a very good racehorse.  At the 1877 Spring Meeting, he won the V.R.C. Handicap against older horses and the following season the Wagga Cup, in the days when it was regarded as a quality race.  Woodlands was also first past the post in the 1878 Hawkesbury Grand Handicap, but his jockey was unable to draw the correct weight, and the horse was disqualified; even with the bridle, Bricky Colley fell short by 3 ounces.  That incident caused a great sensation at the time and the decision cost owner Joe Silberberg a fortune in bets.

The Hawkesbury scales were only new, and it was thought their stiffness prevented correct weight being signalled.   In fact, Silberberg was poorly done by, for the following year the scales were found to be defective.  A big gambler – that Hawkesbury loss was the beginning of Silberberg’s downfall.  He dropped a bundle at the 1880 A.J.C. Autumn Meeting and had to ask for time to settle, which he subsequently did in full but not before selling all he possessed including his bloodstock. Woodlands, at that time off the scene and having had both his forelegs fired, went to a Melbourne buyer for an undisclosed sum while The Alpaca, dam of the Derby winner, went to the Hon. James White for 525 guineas.  Silberberg died some years later a broken man.

Woodlands fared somewhat better.  Pin-fired or not, the old warhorse was still good for one last controversy on the racecourse even in new ownership.  It came in the 1881 Caulfield Cup; the second conducted that year after the V.A.T.C. decided on a switch from the autumn to the spring.  Woodlands made a late run in the race and in the opinion of most onlookers got up on the line.  It seemed that the judge was the only man on the course that didn’t see Woodlands; he failed to place him in the first two while refusing to award a third placing.  As Maurice Cavanough wrote in his book “The Caulfield Cup”: “the very strong consensus of contemporary opinion was that Woodlands was first past the post.”  When Woodlands was finally retired from racing, Norman and Harold Armytage purchased him for their Afton Downs station in the Hughenden district of North Queensland, where he managed to get plenty of local winners from among the station mares.


1876 – The Adventures of Robinson Crusoe!


1878 – The Rise of the Master of Terrara!


  1. Mrs Helen Engle

    Fantastic article. My GG Grandfather Henry Bellingham was a groom at Kirkham and I have inherited an inkstand made from of one of Chester’s feet as a family heirloom. I was wondering if you have any knowledge of my GG Grandfather.
    Regards Helen Engle

    • Ian Ibbett

      Hi Helen, Thanks for your feedback. Your great-great-grandfather is mentioned in two other chapters of Kings of the Turf viz. 1889 ‘The End of an Era’ and 1964 ‘A Pretender Crushed and A Sovereign Crowned’. I’ll check to see if I have anything else in my notes and let you know.
      Regards, Ian

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