There are a lot of contributors to a Melbourne Cup victory. First and foremost, of course, is the horse actually doing the running, while years of work from the trainer also plays a pivotal role. One of the final pieces of the puzzle is the jockey, and these are some of the best of them at the Melbourne Cup over the years.
Bobby Lewis (four wins)
Few outside of the most ardent racing fans have heard of Bobby Lewis, and given he began plying his trade well over 100 years ago, that’s little surprise. Back in 1902, a 23-year-old Lewis led his aptly named mount The Victory to just that, winning his first ever Melbourne Cup in the process. Over the course of a long and established career he would go on to take out the great race on another three occasions, with 25 years spanning his first win and his last win at the event. The four victories he recorded was comfortably the most in history at the time (no one else had even managed three), and nearly 100 years later, remains the equal most ever.
Harry White (four wins)
The only jockey to have matched Bobby Lewis for success at the Melbourne Cup is Harry White, but he took a lot less time to do it. White was a dominant force in the racing scene in the 1970s, and the fact that all four of his Melbourne Cup wins came during that decade is testament to that. In 1974 he won his first on the famous Think Big, and repeated the dose the very next year. In 1978 and 1979 he once again went back-to-back, though on that occasion it was on different mounts — Arwon winning the first and Hyperno the next.
Glen Boss (three wins)
Of the host of Melbourne Cup jockeys to have won the race on three occasions, Glen Boss might have ridden the most unique path to get there. Boss was fortunate enough to saddle up on Makybe Diva in 2003, when she took out the event for the first time. She would extraordinarily go on to become the only horse to ever win the Melbourne Cup more than twice by winning it in three consecutive years, and it was Boss who went along for the ride on each occasion, making him the only jockey to ever win the race three years in a row.
Damien Oliver (three wins)
Damien Oliver has been a consistent presence on the Victorian racing scene for a number of decades, and his three triumphs at the Race That Stops a Nation are testament to the quality of his riding. He first won in 1995 aboard the Lee Freedman-trained Doriemus, while his most famous win came in 2002 when he rode Media Puzzle to victory just days after his brother and fellow jockey Jason died in a fall at Belmont. His most recent win came on Fiorente in 2013, but as an active jockey he has a chance to join the elite company on four wins in the coming years.
A number of other jockeys sit level with Oliver and Boss on three wins, including Kerrin McEvoy, Jim Johnson, William McLachlan and Darby Munro. These six all find themselves in an extremely exclusive club of riders with a trio of Melbourne Cup wins to their names, but it’s Harry White and Bobby Lewis who sit out on top as the most successful Melbourne Cup jockeys in history.