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Which horse was the biggest long shot to win the Preakness Stakes?

The Preakness Stakes has historically been a tough one for underdogs, but it’s not impossible.

2013 Preakness Stakes Set Number: X156521 TK2 R1 F406

The Preakness Stakes will take place at Pimlico Race Course this weekend as Kentucky Derby winner Mage goes for the second leg of the coveted Triple Crown. In a field of just eight horses, Mage is the favorite with 8-5 odds. The horse with the longest odds in this year’s race is Chase the Chaos, who comes in at 50-1, and is one of just three horses with odds of 15-1 or longer.

The Preakness hasn’t traditionally been very favorable to the underdogs. Only four winners have started the race with odds of 15-1 or higher. Last year’s winner, Early Voting, entered with 7-2 odds. But that’s not to say it can’t happen.

In 2013, Oxbow had struggled through spring races before arriving in Maryland. With 15-1 odds, the horse seemed like an afterthought heading to the starting gate at Pimlico. However Oxbow surged at the 138th Preakness Stakes, coming from the sixth post position to win by a comfortable 1 34 lengths.

In 1972, one year before Secretariat’s Triple Crown win, Riva Ridge looked to be on his way to horse racing’s ultimate prize after a dominating win at the Kentucky Derby. However, Pimlico went wild when Bee Bee Bee went off a 19-1, leaving the favorite in the dust.

The biggest long shot to win the Preakness Stakes was in 1975 when Master Derby had the seventh longest odds at 23-1 in a 10-horse field. Just an afterthought. But he came on strong out of the gate, holding off a late surge by the favorite Foolish Pleasure to win by a length.

The Preakness Stakes is Saturday, May 29, with a post time of 6:50 p.m. ET. Live coverage is available on NBC. Live streaming coverage can be found on or the NBC Sports app.