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On Friday evening, October 5, 1894, Sir John arrived in London from Scotland, where he had been shooting, and returned to his residence, Park Place, to prepare for his trip to Kempton Park races the following day to see the Duke of York Stakes. Servants would later recall how he appeared to be in the best of health, not once complaining of any indisposition.
John enjoyed his day at the races though persistent rain had literally dampened the occasion. The baron arrived back home in very wet clothes and for the first time complained of not feeling well. The servants helped him to bed, leaving a glass of warm milk, laced with whisky, by his side.
He was in desperate trouble the next morning, and the services of Sir William Broadbent, M.D. were requisitioned by his physician, Dr. McGuire. Lady Astley and his son were both sent an urgent telegram, but, at six o'clock Wednesday morning, October 12, before they arrived, Sir John Astley died. He had been suffering from Bright's disease which supervened on the chill sustained at Kempton Park.
Sir John was buried on Tuesday, October 16 at Elsham, Lincolnshire. The coffin, which was covered with a Union Jack, was carried from Elsham Hall to the churchyard, a distance of about a quarter of a mile, by employees of the estate.
The eldest son of Sir Francis Astley, Sir John was born on Pincian Hill, Rome, on February 19, 1828, and succeeded his father in 1873. He was educated at Eton and Christchurch, Oxford. In 1858 he married Eleanor, by whom he left several children.
Recalling Sir John's addiction to cigars, a friend said: 'He was never without one. He must have smoked more miles of cigars than any man living.'
Sir John was an enthusiastic patron of the turf and owned several top-class horses including Laura, dam of Petrarch, which won the Two Thousand Guineas and St Leger of 1876.
That year saw Hopbloom carry Sir John's colours - canary jacket, green cap - to victory in the Royal Hunt Cup, but its preparation for the race had not been without incident. Sir John had run Hopbloom in the Ascot Stakes just the previous day, but the horse, ridden by young Hopkins, ran out near the stables before tumbling into the gorse and heather. Hopkins, sent flying, was quickly on his feet and grabbed its bridle. Both horse and jockey seemed okay that evening and Sir John, knowing that Hopwood had an excellent chance in the next day's Royal Hunt Cup, resolved to let the horse run. Hopkins rode an excellent race, winning cleverly, and landing Sir John some £4,000 in bets.
Sir John was to win the race a second time: in 1881, the heavily-weighted Peter, ridden by the legendary Fred Archer, tried to pull up during the race and it took all of Archer's cunning to cajole a winning run from his reluctant partner.
Sir John also owned Hesper (then one of the greatest hurdlers ever seen), Scamp (Goodwood Cup), Blackdown (which landed Sir John the biggest stake of his life in bets when winning the Goodwood Stakes), Gladiator, Actæa and Ostregor, perhaps the best of all. Sir John gave 2,000 guineas for him in 1867 - Ostregor went on to land the 1869 Chesterfield Cup at Goodwood.
In 1879, The Bibury Club Dinner was held at the Grosvenor Arms Hotel in Stockbridge, and it was here, after much good wine had been enjoyed, that a wager between Sir John and his lifelong friend, Caledon Alexander, was struck. For a stake of £500, Sir John would ride his horse Drumhead, a six-year-old, against Caledon's five-year-old mare Brigalia over the Suffolk Stakes course at Newmarket. On the day, Sir John weighed in at 16 stone 6 lbs, while Caledon was 16 stone exactly. The slender Brigalia was simply not built to carry such a weight and, having made the early running, was soon in trouble, leaving Sir John to score an effortless victory.
Elated by this success, a second match was arranged, this time against Billy Bevill on Soloman over the last two miles of the Cesarewitch course. Soloman was an enormous coach horse, as slow as a man but every inch a stayer. Two lengths behind coming to the Bushes, Sir John asked Drumhead for a final effort. instead, the horse faltered and broke down. Sir John recalled the horse as the kindest and quietest of horses who once had been given some whisky before he ran at Shrewsbury. Drumhead liked it so much that he followed Sir John around the paddock for another swig.
Sir John never raced competitively again.
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