Home Run Derby Roundtable: Our Editors’ Picks and Best Bets

The 2021 Home Run Derby will take place on Monday night, and the field is loaded with some of the game’s best power hitters. 

This year, Major League Baseball has opted for a bracket format which allows for several intriguing matchups.

It also gives certain players easier paths to the final round than others, which certainly plays into who you decide to bet on as the winner. Right now, WynnBET has Los Angeles Angels two-way sensation Shohei Ohtani as the favorite to win the Home Run Derby at +225 odds. 

If Ohtani lives up to the hype and makes the final round, it means we won’t be seeing a repeat champion as 2019 Home Run Derby winner Pete Alonso would need to knock out Ohtani in the semifinals to defend his title. 

There are also some intriguing prop bets for the Home Run Derby on WynnBET, including the most home runs in an individual round and the longest home run. 

If you’re looking for some picks to make, or even to fade, here’s what our editors are taking tonight: 

Matt Olson to Win (+700)

Matt Olson is the one player I haven’t heard anyone talk about betting on in tonight’s home run derby, but I think he’s clearly the best value bet. A huge advantage for Olson is that he’s on the weaker side of the bracket, in my opinion. 

Ohtani is the clear cut favorite, and past winner Alonso could also do some damage. Olson doesn’t have to face either of those competitors until the final matchup.

Furthermore, Olson has a relatively easy first round matchup as he’s set to take on Trey Mancini of the Baltimore Orioles, who has had the benefit of playing in the hitter-friendly Camden Yards. 

Olson is truly one of the more underrated hitters in all of baseball, and he’s on pace to set a personal best for dingers in a single-season, despite playing his home games at the Oakland Coliseum, one of the most pitcher-friendly parks in the Majors. He’s the best value on the board in what should be an electric event to watch. -- Iain MacMillan

Trevor Story to Win (+650)

Story has seen his odds fall from +500 in the past few days, but I still love his chances to win the event, and he's providing great value now at +650. Story has the benefit of avoiding Ohtani and Alonso in the bracket, similar to Olson, and if he can get past Joey Gallo in the first round, there’s a chance he finds himself in the final. 

The added altitude in Denver could play into some fatigue for players in this event, and Story has a major advantage in that aspect as well since he will be at home. It’s common to see players wilt in the later rounds, but Story is accustomed to the altitude at Coors Field.

Ballparks certainly play a major role in the derby, and Story has the benefit of playing at Coors Field year round. While the shortstop hasn’t displayed major power numbers this season, he gets to take batting practice at Coors Field all the time, which should have him prepared for the feel of the field and where in the park he can take advantage of his power. 

On top of that, Story will have the support of the home crowd propelling him. It’s always nice to have some extra support and motivation in these events, and hometown players have actually fared very well in recent years. 

Since 2015, two players, Todd Frazier and Bryce Harper, have won the Home Run Derby at their home park. It’s not a fluke that players tend to hit better where they are comfortable, and that should play to Story’s advantage in this year’s Home Run Derby. -- Peter Dewey

Longest Home Run Will Be Over 510.5 Feet (-140)

Rather than lock in on a player to win, I'll focus on a prop bet that I wrote up in detail here at BetSided.

Only once has a home run in the Derby travelled more than 510.5 feet, which is what WynnBET has listed for their "Length of Longest Home Run" prop. Coors Field's temperature at the start of the event is projected to be in the low-90s in the best hitting ballpark in the Major Leagues.

This number is a steal at Wynn, and is already listed as high as 515.5 feet at other sportsbooks which would set an all-time derby record.

Additionally, Major League Baseball has already confirmed that the humidor (which helps provide an even playing field for pitchers in the thin altitude) is unplugged, giving the baseballs an even larger boost to leave the yard.

I anticipate we'll see plenty of moonshots this evening in Denver, with the over on 510.5 feet hitting as early as the first round! -- Ben Heisler

Joey Gallo to Win (+475)

Despite the No. 1 seed Shohei Ohtani getting most of the love in tonight’s Home Run Derby, I’m going with the No. 2 seed Joey Gallo. He’s been on a tear for the last month and a half and is coming into the Derby in a great rhythm. 

Gallo started off slowly in the first two months of the season, only hitting nine home runs in his first 52 games. Over his last 32 games, he’s hit 15 home runs.

WynnBET is giving Gallo the third-best odds to win the Home Run Derby with +475 odds. He is sitting behind Ohtani (+225) and Pete Alonso (+400).

Gallo is going to have a difficult first round facing off against Story, who’s hitting in his home park. However, Gallo’s bat has power behind it, hitting in the 95th percentile of maximum exit velocity. Gallo in essentially batting practice should be just fine. -- Donnavan Smoot

Who are you picking tonight?

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