Histories Most Extravagant Jockeys

Horse racing is one of the most lucrative sports in the world with some of the top jockeys earning hundreds of millions throughout their careers. Japanese jockey Yutaka Take is the current highest earning rider, raking in an eyewatering $796m throughout his 35-year career. Considered a legend in Japan, he is known for his humility, not even owning a smartphone until 2022. In fact, there are not too many current jockeys that boast an extravagant lifestyle, mainly down to the sheer amount of work that they must put into their racing.

However, if the crown was going to go to anyone it may well be Kiwi rider James McDonald. The 29-year-old splashed out over $5m on a six-bedroom, four-car garage property complete with a pool with his TV Star girlfriend Katelyn Mallyon in 2021. It boasts amazing views out onto the Sydney Harbour Bridge, showing that McDonald has not held back in spending his career winnings. With his rides frequenting Horse racing odds betting tips, McDonald has no doubt earnt his life of luxury.

Let’s take a look at some of the other most extravagant jockeys throughout history.

AP McCoy

AP McCoy is one of the most legendary jockeys in racing history. Unbeatable 20 champion jockey titles, tens of millions in winnings and a few broken bones along the way, his career is still remembered fondly after his retirement in 2015. Along with his wife Chanelle, he built his current house from scratch after moving out of their £2.5m, 6,500sq ft home in 2011. Sitting in Lambourn, Berkshire, England, the home features a games room, a 17m wardrobe with Swarovski crystal engraved woodwork and an enormous bathroom complete with TVs. Aside from his giant house, McCoy also owns a £60k Porsche his second since he wrote off his first following another driver allegedly falling asleep at the wheel of his van. He also struck up an unlikely friendship with Brazilian soccer superstar Ronaldinho after the two played together in a charity game. McCoy’s legendary career is matched by his iconic lifestyle.

Laffit Pincay Jr

One of the most winningest jockeys in US racing history, Laffit Pincay has never been afraid of splashing the cash. Until 2018, he lived in a Spanish-Style 5,905sq ft home in Arcadia, California. Originally bought for $1,725,000, it was put up on the market for $3,788,000 five years ago. Though details on his current home are scarce, he is still living in Arcadia, an upscale town known for its excellent school districts. He earnt a whopping $237,120,625 throughout his career and is happy soaking up the sun in Los Angeles County after retiring in 2003.

John R Velazquez

John Velazquez is one of the most successful jockeys in North American racing history. Born in Puerto Rico, he moved to the US in 1990 aged 18 and embarked on one of the greatest riding careers in US history. The hall of famer is a winner of fifteen Breeders’ Cup and six Triple Crown races including 2011, 2017, and 2020 Kentucky Derbies. For his efforts he has racked up over $300 million in earnings and lives very healthily in New York with his wife Leona O’Brien. He has a host of sponsorship and brand deals to add to his wealth.

Willie Shoemaker

Willie Shoemaker was perhaps the first ‘famous’ North American jockey. Rising to prominence in the 1950s, he won eleven triple crowns spanning four different decades. He was pictured with many stars throughout his career, including former actress, singer and playboy playmate Jayne Mansfield. He amassed more than $123 million throughout his thoroughbred career and eventually moved out to San Marino, California after growing up in Texas. The city is known as one of the wealthiest in the nation in terms of household income. He often appeared in advertisements and commercials and quickly became one of the most recognisable faces in horse racing.

Frankie Dettori

The most obvious name on this list, Frankie Dettori is as close to a rock star as you can find in horse racing. The 52-year-old Italian stallion, pardon the pun, has long lived a life of luxury funded by the $212m he has accumulated from his legendary flats career. Dettori left Milan for England aged 14 to pursue a career as a jockey and has never looked back since. It has of course not come without its pitfalls however and his fast-paced lifestyle has caught up with him a few times. He has owned as many as four Ferrari’s, including a £190,000 488 Spider kept in his special heated garage. He owns a modern-day mansion with his wife after putting his former Newmarket home up for sale for £2.5m. In an interview, Dettori even remarked “Jesus Christ, why did I pick such a big house?”. Known for his party boy lifestyle, extravagancy is a word that has become synonymous with Frankie Dettori.