The Top 7 Winningest Horse Racing Jockeys of all Time

The Top 7 Winningest Horse Racing Jockeys of all Time

 Winningest Horse Racing Jockeys of all Time

Winning Horse Racing Jockeys of all Time

Famous jockeys are part and parcel of horse racing. Measuring their success is extremely subjective, however. There are different ways of looking at who is the “best” horse jockey ever without settling the debate.

One metric for ranking famous horse jockeys is the prize money they rake in. You can also look at quality and quantity of horse races won.

There’s also career longevity to consider, international success in big events and striking up memorable partnerships with famous racehorses too. Comparing jockeys from different eras and places, and with different riding styles is always difficult.

1. Russell A. Baze

Starts: 53, 578

First-Place Finishes: 12,842

Russell A. Baze began his horse racing journey back in 1974 and just recently hung up his saddle in 2016. He finished his career with the most wins in North American Thoroughbred Horse Racing history, a feat he accomplished in December of 2006. The Vancouver native went on an impressive streak of leading all North American jockeys with 13 wins from 1992 to 2014. Baze was officially honored when he was inducted into the National Museum of Racing and Hall of Fame in 1999The Top 7 Winningest Horse Racing Jockeys of all Time


2. Mike E. Smith

Proof, as if it were needed, that age is no barrier to success is embodied by Mike Smith. At the age of 52, he partnered with Justify to claim the US Triple Crown in 2018.

It was the highlight of his career despite being towards the end of it.

Smith is synonymous with success at the Breeders’ Cup too, winning 26 races at the premier Flat thoroughbred meeting in America.

Arrogate, who has won some of the richest races staged in the world, is another of Smith’s high-profile equine partners in a career that began in 1982.

He has also set a new record for most American Grade 1 successes in the saddle, surpassing honorable mention Jerry Bailey, at the end of 2019.


3. Sir Gordon Richards

Sir Gordon Richards, a 26-time champion.

Born: 05/05/1904

Died: 11/10/1986

Country: UK

Career Wins: 4,870

British Classic Wins: 14

Any list of famous horse jockeys needs to have a 26-time champion on it. That’s what Sir Gordon Richards managed during a glittering career in the saddle.

While he wasn’t as prolific in the British Classics as some of the other UK based jockeys on our list, Richards set a record that may never be broken.

Longevity and sustained success are both boxes firmly checked in this case.Richards became a fine racehorse trainer after retiring from riding and son Nicky still has stables at Penrith on the edge of Lake District.

Sun Chariot, a rare winner of the UK Fillies’ Triple Crown, and Tudor Minstrel are perhaps Richards’ most famous equine partnerships from the 1940s.


4. Chris J. McCarron

Wins: 7,141

Total Earnings: $263,986,005

Winning the Breeders’ Cup Classic once is an impressive feat, but doing the it five times is  stellar. That is the case for jockey Chris J. McCarron, who won the prized race a quintet of times between 1988 and 2001. Add two victories each at the Kentucky Derby, Preakness Stakes and Belmont Stakes, and it starts to make sense why McCarron has one of the highest total purse amounts the sport has ever seen. He was inducted into the National Museum of Racing and Hall of Fame in 1989


5. Bill Shoemaker

He rode 11 US Triple Crown winners, but never captured all three prizes in the same season.

Although he is only third on the all-time list of winning most American Flat jockeys, Shoemaker had a career strike rate over 21 percent.

In other words, about one in every five horses he ever rode won their races.

He topped the earnings table 10 times in his career in the saddle, holds a deserved place in National Museum of Racing and Hall of Fame and was champion US jockey five times in the 1950s.

Shoemaker went on to earn more than treble what he made riding as a racehorse trainer once he retired after 41 years of being a jockey.


6. Lester Piggott.

Lester Piggott takes the second spot in our list of famous horse jockeys, because he not only had longevity, sustained success at the top in the UK and Ireland but international success too.

Piggott’s way of riding racehorses has been imitated ever since.

With 30 British Classics under his belt, including the UK Triple Crown of 2,000 Guineas, Epsom Derby and St Leger with Nijinsky in 1970, he partnered many of the best Flat thoroughbreds in Europe over four decades.

An 11-time UK champion Flat jockey, Piggott even has the British horse racing awards – the Lesters – named after him. And with nine wins, he is the most successful rider in Epsom Derby history.

Piggott also holds the record for most victories in the Ascot Gold Cup (11), Dewhurst Stakes (10), July Cup (10), Coronation Cup (nine) and many other Group 1 races.


7. John R. Velazquez – jockey

No jockey on planet earth can claim to have bagged more prize money than John Velazquez.

The Puerto Rico native has in excess of $415,000,000 in career earnings and counting.

With well over 6,000 winning rides, Velazquez is still seeking the career Triple Crown in the USA.

Just glory in the Preakness Stakes eludes him with two wins apiece in the Kentucky Derby and Belmont Stakes. Velazquez has topped the prize money charts twice in America and remains consistent as ever.

Kitten’s Joy and Scat Daddy, who have both become huge influences on thoroughbred breeding as sires of great racehorses since going to stud, are among his most famous equine partners.

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