The first-ever virtual “Kentucky Derby” will be broadcast on NBC on May 2 when the 13 Triple Crown winners will square off in a simulated race. This wildly entertaining showdown features some of the most renowned Thoroughbreds that ever set foot on U.S. soil. And on top of every great horse, was a great rider.
Here is how I rank the Triple Crown-winning jockeys:
  1. Eddie Arcaro -- The lone pilot to guide home two Triple Crown winners (Citation and Whirlaway) tops the list. Regarded by many historians as the greatest jockey in the history of American Thoroughbred racing, the Italian-American booted home five Kentucky Derby winners among his 17 classic wins during an illustrious career. “The Master” retired in 1962 with more than 4,700 career victories and got his Hall of Fame call in 1958. 
  2. Johnny Longden -- One of the top riders in history, “The Pumper” amassed in excess of 6,000 wins in his lifetime. He was a champion jockey on multiple occasions who rode some of the top runners of his generation, led by 1943 Triple Crown star Count Fleet. A founding member of the Jockeys’ Guild, Longden became the first person in history to both ride and train a Kentucky Derby winner after Majestic Prince captured the 1969 Run for the Roses. He became a Hall of Fame member in 1958. 
  3. Jean Cruguet -- A standout rider in Europe, Canada, and the United States alike, Cruguet is best known domestically for his efforts aboard the superb Seattle Slew, who in 1977 became the first undefeated Triple Crown winner in history. Known for his low and tight riding style, the French native compiled more than 2,400 lifetime victories. And he is also regarded as the first pilot to stand in the stirrups and wave his crop in the air in celebration after crossing the wire first, a common practice for today’s riders. 
  4. Steve Cauthen -- It didn’t take long for this all-timer to make his presence felt on the racetrack. “The Kid” booted home his first winner in 1976, and he immediately was the champion apprentice and jockey the following season. To emphasize just how good Steve Cauthen was in the saddle, it must be noted that he was both the 1977 Associated Press Male Athlete of the Year, as well as Sports Illustrated’s 1977 Sportsman of the Year. Also a three-time British Champion Jockey who rode 10 English classic winners, this genius was atop Affirmed for his 1978 Triple Crown sweep. His Hall of Fame induction came in 1994. 
  5. Ron Turcotte -- Canadian-born sensation is a Hall of Fame member in his native land, and in the United States, as well. “Ronnie” captured the Kentucky Derby and Belmont Stakes in 1972 with Riva Ridge, but he became an international hero because of his work atop the immortal Secretariat in 1973. The brilliant pilot brought home 3,032 winners before his riding career was cut short following an horrific injury in 1978. 
  6. Mike Smith -- “Money Mike” seemingly doesn’t age. One of two current jockeys on this list, Smith continues to ride at the highest level well into his 50’s and received his Triple Crown glory aboard Justify in 2018. The author of more than 5,400 wins to date, he has been on the backs of countless standout horses while earning notable wins in the United States, Canada, Ireland, and Dubai. Smith has been a Hall of Fame member since 2003.
  7. Earle Sande -- South Dakota native entered the Thoroughbred game in 1918 and was champion jockey on three occasions (1921, 1923, 1927). Following his final retirement from riding in 1932, Sande became a conditioner and earned top trainer marks in 1938. The 1955 Hall of Fame recipient was in the silks for nine classic wins, including each leg of the Triple Crown atop Gallant Fox in 1930
  8. Victor Espinoza -- The third time was the charm in 2015 for this Mexican native, who had arrived at Belmont Park on two previous occasions with a chance to capture the Triple Crown. He would not be foiled with the uber-talented American Pharoah, however, who broke a 37-year Triple Crown drought. The seven-time classic winning pilot is among the top riders of this century and was inducted into the Hall of Fame in 2017. 
  9. Charles Kurtsinger -- Bluegrass-bred won six Triple Crown races in total, including three when piloting home the mighty War Admiral in 1937. “The Flying Dutchman” had a superb 7-year run as a jockey, but his career was cut short due to injury in 1939. He was inducted into the Hall of Fame in 1967.
  10. William Saunders -- “Smokey” is a member of the Canadian Horse Racing Hall of Fame and is forever etched in Triple Crown lore after sweeping the classics atop Omaha in 1935. Born in Calgary, Alberta, Saunders had his career interrupted after joining the United States Army for a 4-year term. He retired in 1950. 
  11. Johnny Loftus -- The jockey responsible for the first Triple Crown winner aboard Sir Barton in 1919, Loftus had an excellent, though brief, career. The Chicago native piloted 580 first-place finishers during his 10-year run, eventually retiring at the conclusion of 1919 to become a trainer. He was voted into the Hall of Fame in 1959. 
  12. Warren Mehrtens -- Brooklyn native guided 614 winners home in his career before retiring in 1952 to work as a race steward at Keeneland Race Course. He rose to national prominence after piloting Assault to Triple Crown glory in 1946.