You’d think that the Home Run Derby would be a pretty straightforward sporting event to handicap, but the reality is that it’s a crapshoot, especially with the new format.

Last year’s Derby, the first under the new format, was won by Teoscar Hernandez, who had the sixth-longest odds of any player in the field.

Even more surprising was the fact that none of the four favorites entering the competition – Pete Alonso, Adolis Garcia, Marcell Ozuna, and Gunnar Henderson – made it out of the first round. 

Perhaps it was just a weird outlier, but the fact that none of the projected favorites, including a two-time winner in Alonso, made it out of the opening round suggests that this new format breeds more chaos than previous iterations.

Instead of pitting individuals against one another from the outset, the current format gives each of the eight players three minutes and a maximum of 40 pitches (whatever comes first) to hit as many home runs as possible. After the limit is reached, they get a bonus period to add to their total before recording three outs (non-home runs). 

The four players who hit the most homers are then seeded and put into a bracket, with each round (1 vs. 4, 2 vs. 3) following the same format as the first, but with a shorter clock (two minutes or 27 pitches).

Whatever the reason, these new rules seemed to benefit the underdogs, and it was Hernandez and Bobby Witt Jr. who made it to the final, which was won by Hernandez, 14-13.

None of the players from last year’s Derby are participating in 2025, which levels the playing field even further.

Seattle’s Cal Raleigh is the current betting favorite at +295. Raleigh leads the Major Leagues with 38 home runs, which is already four more than his previous career high. 

Pittsburgh’s Oneil Cruz, who has just 16 home runs but leads the Major Leagues in average exit velocity, is right behind Raleigh at +320.

James Wood, a rising star for the Washington Nationals, is the third choice at DraftKings with +475 odds.

Matt Olson (+800), Brent Rooker (+850), Byron Buxton (+950), Jazz Chisholm Jr. (11/1), and Junior Caminero (12/1) round out the field. 

There is no right or wrong way to handicap the Home Run Derby, but it does seem like a good idea to swerve the chalk. Raleigh, because of his home-run total, and Cruz, because of his batted-ball stats, are logical favorites, but this isn’t a competition that is always ruled by logic, and we’d want a bigger payout in an event that is a guessing game.

Continuing the process of elimination, we’ll draw a line through Jazz Chisholm Jr., who has been battling injuries and just isn’t a prolific home run hitter. If you were going off true odds, Chisholm would likely be the biggest price, but since he’s getting hit with a Yankee Tax. 

By throwing out the three players at the top, we’ve whittled down our choices to five players between +800 and 12/1.

The four participants left in our pool have similar stats, but a couple of things stand out to help direct us to our two picks for our best bets on Monday night.

Matt Olson is our first pick at +800.

A late replacement for the injured Ronald Acuna Jr., Olson is playing in his home park, which could give him enough of a leg up against the rest of the pack to make this price worth a wager. Olson also boasts the second-best average exit velocity in the field behind Cruz.

The other player we’re backing is Caminero. With 23 home runs and strong batted ball stats, there’s not much that separates the Tampa Bay Ray from the rest of this field. He’s just not as well-known as some of the other participants, which is allowing us to get him at a discounted price.

Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry. He loves using game theory to help punters win bracket pools, find long shots, and learn how to beat the market in mainstream and niche sports.