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MLB Best Bets: Top Starting Pitcher Prop Bets for Monday 6/2/25

MLB Best Bets: Top Starting Pitcher Prop Bets for Monday 6/2/25

Published:

By: Zach Thompson

Monday features seven brand new MLB series across the diamonds, starting at 6:40 p.m. ET in Miami and continuing through the last game of the night, which starts at 10:10 p.m. ET in Los Angeles. With 14 hurlers ready to take the mound, let’s take a look at my top starting pitcher prop bets for the night, including options from Brady Singer, Logan Webb and Joe Ryan.

Every day of the season, DraftKings Sportsbook offers multiple ways to get in on the action with player props, Moneylines and picks against the spread from each MLB contest. You can also pick series winners, award winners and team futures, so be sure to check out all the options available on the MLB page of DraftKings Sportsbook.

Best Starting Pitcher Prop Bets on DraftKings Sportsbook

Brady Singer under 4.5 Strikeouts (-130)

Singer and the Reds host the Brewers in the first game of this NL Central matchup. The Brew Crew come in hot after sweeping the Phillies and Red Sox and winning seven straight. Over those seven games, the Brewers have just an 18% strikeout rate. They have a 21.5% strikeout rate on the season, which ranks in the middle of the pack in the majors.

Singer has a 19.6% strikeout rate with 49 strikeouts in his 58 2/3 innings this season. His strikeout numbers have been trending down, though, with four strikeouts or fewer each of his last six starts. His last start with five or more strikeouts came on April 23 against the Marlins.

Whether the Brewers stay hot and deliver as one of my top MLB DFS stacks of the day or if Singer holds them in check, he will likely be under this strikeout line based on how he’s been throwing recently and how the Brewers have limited punchouts over the last few games during their streak.


Logan Webb 6+ strikeouts (+130)

On the other side of the strikeout over/unders, I’m targeting Logan Webb’s over as one of my top starting pitcher props on Monday. He and the Giants are back home after a long road trip to welcome in the Padres, whose offense has been struggling over the last few weeks.

Webb has just a 5-5 record in his 12 starts but has been very effective with a 2.82 ERA backed up by an even better 2.19 FIP. He has a 27.9% K% and 10.31 K/9, which would both be career-highs if he maintains them the rest of the season.

In his last start, he racked up 10 strikeouts in a loss to the Tigers, raising his average to exactly 7.0 strikeouts per game. He struck out six against the Padres when he faced them in San Diego at the end of April, and that was in just five innings. If he’s able to stick around a little longer on Monday, he should be able to hit this prop at plus money.

Another reason Webb deserves a look here is the Padres’ offense. San Diego is hitting only .202 over the last two weeks, the lowest total in the majors. Their .270 wOBA is the fourth-lowest over that span, so Webb should be able to limit them and stick around long enough to get at least six strikeouts in Monday’s matchup.


Joe Ryan to record a win (+125)

Picking on the A’s has been a very viable strategy lately since they have cratered after a much stronger start. Most of their issues have been with their pitching staff, but their offense has cooled down as well. The Athletics have dropped 17 of their last 18 games, and Luis Severino has rough home splits that make it look like Ryan should have plenty of run support on Monday.

Ryan has been solid for Minnesota so far this season, picking up five wins in his 10 starts. Overall, he has a 2.57 ERA, 3.21 FIP and 0.83 WHIP, limiting opponents to a .190 batting average. He has given up zero or one run in five of his last six games since getting hammered in Atlanta. Aside from that outing, though, he has been locked in lately.

So far this season, he has pitched well enough to get more wins than he has, and since I think the Twins will have no trouble scoring runs for him on Monday against the A’s, I think he’ll be able to claim a victory in the late game.

Zach has been part of the DraftKings team since 2017 and covers baseball, basketball, golf, football and any other sport that offers DFS fun. He has been playing fantasy sports since box scores were only available in the newspaper the following day. Even though he grew up almost 8,000 miles away in Guam, he is a diehard Boston sports fan but will take a fantasy value play wherever he can get it, even if it’s from the Yankees.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user (my username is z.thompson) and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.