Imagining What Major Stakes Horse Races Look Like as March Madness Games

TORONTO — By Matthew Lomon

We’ve reached that magical time of year when the Cameron Krutwig’s and Doug Edert’s of the world rise from the depths of obscurity to national superstardom, even if only for a moment. To celebrate the most exciting three weeks in collegiate sports, your pals at MyRailbirds took five historic matchups from the Division I Men’s NCAA Basketball Tournament and reimagined them as major stakes races.

A pair of unimaginable upsets, slam-dunk favorites, and one mild miracle await below.

Unimaginable Upsets

Horse: T J’s Lucky Moon, 2002 King’s Plate (82-1)

Game: No. 16 UMBC (+20.5) defeats No. 1 Virginia, 2018 Round of 64

Quick show of hands, who knows what UMBC stands for? Those who said University of Maryland, Baltimore County would be correct. Bonus points to the folks that added “Retrievers” at the end of their answer. Jokes aside, you get the point.

Led by senior guard Jairus Lyles, UMBC dismantled number one seeded Virginia 74-54. On top of being 20.5-point underdogs, the Retrievers sat at +2500 on the money line. The Cavaliers, on the other hand, closed at -10,000.

Much like fans of both programs will never forget the events of March 16, 2018, the same can be said for those who witnessed 82-1 lottery ticket T J’s Lucky Moon win the 2002 Queen’s Plate. Captained by rider Steve Bahen, the second longest shot on the board pulled off a miracle to stun the field and return a whopping $166.

But the good times didn’t last long for the gelding or UMBC. The former never won another race and the latter got bounced by Kansas State in the Round of 32.

Horse: Rich Strike, 2022 Kentucky Derby (80-1)

Game: No. 16 Farleigh Dickinson (+23.5) defeats No. 1 Purdue, 2023 Round of 64, 63-58

Let’s show some love to Hackensack, New Jersey, the town of 45,000, otherwise known as the home of Farleigh Dickinson University. The 16-seeded Knights became an overnight sensation after besting reigning Naismith Trophy winner Zach Edey and the Purdue Boilermakers 63-58 in the opening round of last year’s tournament.

Coming in, Purdue had the fourth-best odds of winning the whole thing at +1000, while FDU found itself in the “Everyone else” category at +20,000 or longer. With the win, Farleigh Dickinson pulled off the largest upset in NCAA Tournament history by point spread (+23.5).

While not quite the biggest upset in Kentucky Derby history, Rich Strike, at 80-1, pulled off the impossible as the board’s least favored runner in 2022. In what was his debut at the Grade 1 level, Rich Strike authored one of the finest rallies in Derby history to steal the $3 million contest by three-quarters of a length.

The monumental score paid a jaw-dropping $163.60. The same $2 bet on FDU money line at +2000 resulted in a $42 payout.

Slam-Dunk Favorites

Horse: Big Brown, 2008 Preakness, (1-5)

Game: No. 1 Duke (-5.5) defeats No. 6 Michigan, 1992 Championship Game

The formula for winning a national title is a mystery that eludes 63 programs each year. Fortunately for Duke, and other Yankees/Cowboys/Lakers fans, the formula begins and ends with coach Mike Krzyzewski. While the variables change each year, the 1992 Blue Devils found the perfect balance with Christian Laettner and Bobby Hurley.

Inside a rocking H.H.H. Metrodome, the three-headed monster trounced the Michigan Wolverines 71-51 to hand Coach K his second of five NCAA Tournament titles.

Speaking of trouncings, 1-5 favorite Big Brown made quick work of 11 running mates in a 5 ¼-length Preakness triumph at Pimlico back in 2008. The Richard E. Dutrow Jr. charge, who won seven of eight career races, including four Grade 1 contests, barely broke a sweat in the $1 million affair to reward his backers with $2.40.

There was no crumbling under the pressure for these two champions. It was nothing more than a simple clock-in and clock-out.

Horse: American Pharoah, 2015 Belmont, (3-5)

Game: No. 1 Villanova (-6.5) defeats No. 3 Michigan, 2018 Championship Game 79-62

Unless you have a connection to the school, watching the pre-tournament favorite hoist the trophy isn’t exactly the most thrilling conclusion to the average fan. Then again, there’s usually a good reason the favorite is the favorite, and that was clear with the 2018 Villanova Wildcats.

Equipped with five future NBA players, the Jay Wright-led squad ran the Michigan Wolverines out of the Alamodome in a 79-62 rout. With the 17-point victory, the Wildcats won all six of their tournament matchups by double-digits.

Eleven starts, nine wins, and $8.6 million in earnings later, singling out one moment from the sea of dominance that was American Pharoah’s career wasn’t easy, but the 2015 Belmont is a mighty fine choice. Closing as the 3-5 favorite, the revered Zayat Stables product toyed with the competition in a front-leading 5 ½-length drubbing. The sizable score ended up being the sixth of American Pharoah’s eight wins at the Grade 1 level.

While bettors’ faith may have been rewarded, their pockets didn’t see much of a boost with a $3.50 return.

Mild Miracle

Horse: Drosselmeyer, 2011 Breeders’ Cup Classic (14-1)

Game: No. 3 Syracuse (+5.5) defeats No. 2 Kansas, 2003 Championship Game, 81-78

Carmelo Anthony never got to experience the glory of lifting the Larry O’Brien over his 19 NBA seasons, but he was able to win the National Championship in his lone season at Syracuse. Regarded as the best player ever produced by the Orange, a then-freshman Anthony willed his team to an 81-78 victory over Kansas as 5.5-point dogs in 2003’s edition of the big game.

At that margin, Syracuse didn’t necessarily pull off the upset of the century, yet they still benefited from a mild miracle in the form of 18 missed Jayhawk free throws to make it happen.

Drosselmeyer, at 14-1, found himself grouped in the middle-tier of contenders for the 2011 Breeders’ Cup Classic. Unlike Syracuse, however, the William Mott trainee delivered his own mild miracle. Running from the seventh position down the stretch, Drosselmeyer found another gear late to zoom past the pack for his second Grade 1 trophy.

Like Anthony, Drosselmeyer couldn’t have asked for a better way to go out. The final race of the Kentucky-bred’s career fetched a return of $31.60.