The Preakness Stakes is the second leg of the prestigious Triple Crown series and almost always features a surprise or two. This year’s Kentucky Derby Presented by Woodford Reserve winner Medina Spirit will attempt to capture the Preakness this Saturday at Pimlico in Baltimore. Medina Spirit and his jockey John Velazquez will have plenty of competition trying to derail their Triple Crown bid. Let’s take a closer look at all of the riders who’ll attempt to claim the spotlight at the Preakness Stakes.

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John Velazquez

Age: 49

Originally from: Puerto Rico

Previous rides in Preakness: 10

Best finish: 2nd in 2011 (Animal Kingdom), 2013 (Itsmyluckyday) and 2020 (Authentic)

His 2021 Preakness horse: Medina Spirit

Newly-minted four-time winning Kentucky Derby jockey John Velazquez is still in search of an elusive Preakness Stakes victory. He finished second in the race last year while riding eventual Horse of the Year Authentic. This year, he’ll again have a strong chance in the race while riding Derby winner Medina Spirit. Originally from Puerto Rico, Velazquez launched his riding career in 1990 and fairly quickly established himself as one of the top jockeys in the country. He earned the Eclipse Award for outstanding jockey in 2004 and 2005. By 2012, Velazquez had been inducted into the Hall of Fame. He has maintained his status as an elite rider since and, in addition to his four Kentucky Derby victories, he has a pair of Belmont Stakes triumphs included among nearly 6,300 career wins.

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Irad Ortiz Jr.

Age: 28

Originally from: Puerto Rico

Previous rides in Preakness: 2

Best finish: Fifth in 2018 (Lone Sailor)

His 2021 Preakness horse: Midnight Bourbon

Irad Ortiz Jr. is considered by many to be the best jockey in America right now. He’s won three consecutive Eclipse Awards for Outstanding Jockey and he leads all riders in wins in 2021 by a wide margin. At just 28 years old, Ortiz already has 11 wins at the Breeders’ Cup and a Belmont Stakes victory (Creator, 2016). However, Ortiz has only had two prior rides in the Preakness Stakes and he’s yet to make a major impact in the middle jewel of the Triple Crown. This year, he’ll be aboard Midnight Bourbon in the Preakness. The horse finished sixth in the Kentucky Derby (Mike Smith was his rider there) which was pretty impressive considering he was bumped at the start of the race and travelled fairly wide throughout. A less adventurous journey in the Preakness could lead to an even better result for Ortiz and Midnight Bourbon. 

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Joel Rosario

Age: 36

Originally from: Dominican Republic

Previous rides in Preakness: 6

Best finish: Second in 2014 (Ride On Curlin), 2015 (Tale of Verve) and 2019 (Everfast)

His 2021 Preakness horse: France Go de Ina

It would be hard to ride as well as Joel Rosario has in the Preakness Stakes without having yet emerged victorious in the race. Rosario has only finished outside of the top four once in his six career Preakness starts, and three times he’s finished second. This year, he’ll be on longshot France Go de Ina who will be making his first U.S. start following four races in Japan and Dubai. Regardless of the outcome, Rosario is well on his way to a Hall of Fame career. He has won the Kentucky Derby, owns a pair of victories in the Belmont Stakes and has 13 wins in the Breeders’ Cup. 

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Jose Ortiz

Age: 27

Originally from: Puerto Rico

Previous rides in Preakness: 3

Best finish: Fourth in 2018 (Good Magic)

His 2021 Preakness horse: Risk Taking

Jose Ortiz is the younger brother of Irad Ortiz and it has become common for them both to have rides in America’s biggest races. Jose entered 2020 off of three consecutive years in which he finished first or second in the nation in purse earnings. In 2017, he won the Eclipse Award as the top jockey in the nation. He’s also a three-time Breeders’ Cup winner, a Belmont Stakes winner (2017, Tapwrit), and has captured multiple riding titles in New York. When it comes to the Preakness Stakes, Jose’s best finish in the race came in 2018. He was fourth that year with the Chad Brown-trained Good Magic. Ortiz and Brown will reunite at the Preakness again this year with Risk Taking, who won the Withers Stakes in February.

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David Cohen

Age: 36

Originally from: California

Previous rides in Preakness: none

Best finish: n/a

His 2021 Preakness horse: Keepmeinmind

Fresh off of his first start in the Kentucky Derby, journeyman jockey David Cohen is about to experience riding in the Preakness for the first time. Cohen’s career dates back to 2004 when he started riding in California. He ultimately moved East and went on to win riding titles at Delaware Park and Philadelphia Park (Parx Racing). In 2009, Cohen ranked sixth in the country in wins while moving to New York, site of his dead-heat victory aboard Golden Ticket (at odds of 33.50-to-1) in the 2012 Travers Stakes. But in 2014, an injury combined with personal considerations led to a three-year hiatus from racing. He returned in late 2017 and posted back-to-back 100-win seasons in 2018 and ’19. He has also scored four graded stakes victories since his comeback began, the most recent of which was aboard Keepmeinmind in the Kentucky Jockey Club Stakes last November. Cohen and Keepmeinmind will team up again in the Preakness after a respectable seventh-place finish in the Kentucky Derby at odds of 49-to-1.

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Javier Castellano

Age: 43

Originally from: Venezuela

Previous rides in Preakness: 8

Best finish: Won in 2006 (Bernardini) and 2017 (Cloud Computing)

His 2021 Preakness horse: Crowded Trade

A member of horse racing’s exclusive 5,000-win club, Javier Castellano also owns one of the more impressive Preakness résumés of any jockey in this year’s race. Castellano made his first splash at Pimlico when he won the 2006 Preakness aboard Bernardini. Eleven years later, Castellano and Cloud Computing were overlooked by bettors when they won the 2017 Preakness at odds of over 13-to-1. Notably, Cloud Computing was owned by Klaravich Stables and trained by Chad Brown. Those same connections own and train Crowded Trade, who’ll be Castellano’s horse in this year’s Preakness. The horse has only run three times in his career and figures to be among the top contenders to pull off a mild upset at Pimlico.

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Mike Smith

Age: 55

Originally from: New Mexico

Previous rides in Preakness: 18

Best finish: Won in 1993 (Prairie Bayou) and 2018 (Justify)

His 2021 Preakness horse: Concert Tour

Both John Velazquez and Mike Smith are testaments to the old adage that age is just a number. At 55, Smith is the most senior rider in this year’s Preakness and he’s still at the top of his game. Inducted into the Hall of Fame in 2003, Smith has racked up more than 5,600 career wins. He’ll forever be remembered for winning racing’s Triple Crown aboard Justify in 2018. That year’s Preakness was impacted by a massive downpour of rain before the race and thick fog during the race. Smith and Justify emerged from it in front and went on to win the Belmont Stakes three weeks later. This year, Smith will be aboard Concert Tour, another highly-regarded horse for seven-time Preakness-winning trainer Bob Baffert.

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Ricardo Santana Jr.

Age: 28

Originally from: Panama

Previous rides in Preakness: 2

Best finish: Third in 2018 (Tenfold)

His 2021 Preakness horse: Ram

Ricardo Santana Jr. has made the most of his two opportunities to ride in the Preakness Stakes but he’ll riding a longshot this year for Hall of Fame trainer D. Wayne Lukas. The horse’s name is Ram and his career started with eight straight losses. He comes in off of two consecutive wins against lesser competition. As for Santana, he’s become one of the top riders in America – leading the Oaklawn Park jockey standings in wins from 2013-18 and again from 2020-21 – and he picked up a second Breeders’ Cup win last year while riding Fire at Will in the Juvenile Turf Presented by Coolmore America. Their odds that day were 30.20-to-1. So, if you’re looking for a rider who’s capable of winning aboard a longshot, Santana might be your guy.

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Flavien Prat

Age: 28

Originally from: France

Previous rides in Preakness: 0

Best finish: NA

His 2021 Preakness horse: Rombauer

Already regarded as one of the best jockeys in North America at age 28, Flavien Prat will be making his first appearance in the Preakness Stakes. Originally from France, Prat initially came to the U.S. in 2009 and began riding periodically during the winter in Southern California. His first full season in North America was in 2015, and he finished second in the standings of the Del Mar summer meet. In the years since, he’s won multiple riding titles in California. Prat’s crowning achievement came in 2019 when a disqualification led to him and his horse Country House winning the Kentucky Derby. This year, Prat’s Preakness hopes rest on the ability of Rombauer to improve off of a third-place finish in his most recent start, the Toyota Blue Grass Stakes at Keeneland in early April.

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Luis Saez

Age: 28

Originally from: Panama

Previous rides in Preakness: 1

Best finish: Second in 2018 (Bravazo)

His 2021 Preakness horse: Unbridled Honor

In a short period of time, Luis Saez has made a name for himself as one of the best riders in the country. Just 28 years old (he turns 29 four days after the Preakness), Saez has already won more than 2,600 races including over 120 victories in graded stakes races. He recently finished fourth in the Kentucky Derby aboard the favorite Essential Quality. Since that horse isn’t coming back to challenge Medina Spirit in the Preakness, the opportunity to ride another horse presented itself to Saez. He’ll be aboard late closer Unbridled Honor. The horse finished second in the Stonestreet Lexington Stakes in his start prior to the Preakness.