Which current jockey has won the Cheltenham Gold Cup most often?
The most successful jockey in the history of the Cheltenham Gold Cup was Pat Taaffe, who partnered the legendary Arkle to three consecutive victories in 1964, 1965 and 1966 and added a fourth, courtesy of Fort Leney, also trained by Tom Dreaper, in 1968. However, of jockeys still riding, two have won the Cheltenham Gold Cup twice apiece.
The first of them is four-time British Champion Jockey Richard Johnson, who won the Cheltenham Gold Cup for the first time on Looks Like Trouble, trained by Noel Chance, in 2000. A 30-length winner of what is now the Brown Advisory Novices’ Chase at the 1999 Cheltenham Festival, Looks Like Trouble was pulled up in the King George VI Chase at Kempton, but made it 2-2 at the Festival when staying on gamely to beat Florida Peark by 5 lengths.Later in his career, in 2018, won the Cheltenham Gold Cup again, on Native River, trained by Colin Tizzard, who got the better of an epic duel with Might Bite to win by 4½ lengths.
The second dual Gold Cup winning jockey in the current ranks is, of course, Paul Townend, who recorded back-to-back victories on Al Boum Photo in 2019 and 2020. On the first occasion, Al Boum Photo was only third choice of four runners trained by Willie Mullins but, nevertheless, ked turning for home and stayed on strongly to win by 2½ lengths. Later that year, Townend succeeded Ruby Walsh as stable jockey to Willie Mullins and rode at his first Cheltenham Festival in that capacity in 2020. As defending champion, Al Boum Photo was sent off favourite for the Gold Cup and, although all out in the closing stages, held on to win by a neck.