Who doesn’t love an underdog?
Betting on an underdog is the easiest way to get the most bang for your buck with a single wager, yet it’s always a somewhat risky endeavor. I mean, they’re underdogs for a reason, right? Still, there’s no sport where the underdog comes through more often than in baseball. It’s a 162-game season. Even the best teams are going to lose about 60 times a year.
With that in mind, here are the teams I would be gravitating towards if I were looking to back an underdog on Monday night on the DraftKings Sportsbook.
Best Underdog MLB Bets, Picks
Pirates ML (+123)
This is less an endorsement of the Pirates than it is a reflection of how little I trust the Royals. On May 12, Kansas City was riding high. The team was seven games above .500 and it seemed like the Royals were going to build on the success that got them to an ALDS series last fall. However, since that day, Kansas City is just 18-30 in its last 48 games. Across the past 30 days, the Royals’ 78 wRC+ is the third-lowest mark in MLB. Is Pittsburgh one of the two clubs below Kansas City? Yes. But at the end of the day, this is a clash between two very flawed teams. These are the kind of situations where you simply hold your nose and back the side at plus-money.
Diamondbacks ML (+101)
Look, no one has all that much faith in Zac Gallen at this point. That said, how much trust can you really have in Yu Darvish? The veteran will make his season debut for the Padres this evening in San Diego. The 38-year-old has only made five starts at the MLB level since the end of May 2024. In his last “full” season in 2023, Darvish posted a career-worst 4.56 ERA. Arizona’s pitching staff has been disappointing so far in 2025, as the team has suffered from a crushing mix of underperformance and injury. Still, the Diamondbacks’ lineup is one of the most dangerous in MLB, as evidenced by a 113 wRC+ that ranks fourth in all of baseball. This team can bang with the best of them and Darvish might get a rude welcome back to the majors on Monday night.
Guardians ML (+113)
I mean… They have to win at some point, right? Right?! Coming into Monday’s tilt with the Astros, the Guardians have dropped their last 10 games. It’s not been pretty and the bats have been virtually non-existent. Still, in terms of good news, Cleveland’s ace, Tanner Bibee, will take the mound this evening in Houston. Bibee is directly on the heels of a very bad outing against the Cubs, yet the right-hander does own a 3.13 FIP and a 25.7% strikeout rate dating back to May 22. Don’t let the 4-9 record fool you, Bibee been as solid in 2025 as he was in 2024 and 2023. On the other side, rookie Colton Gordon will toe the rubber for the Astros. The lefty is surrendering 1.79 home runs per nine and he doesn’t miss any bats, at least that’s what a seventh percentile whiff rate suggests (18.5%). The Guardians clearly have the advantage in this pitching matchup. Whether that’s enough for the team’s first win in July remains to be seen.
