Million Dollar Musings: MLB DFS Picks Today for Monday 5/26

by Dave Potts (CheeseIsGood) Last Updated 2025-05-26 15:42:17 Premium Content Part of the product MLB DFS

Whether you are looking for the top pitchers or the best stacks, Dave Potts (aka CheeseIsGood) has you covered with an extensive deep dive into his MLB DFS picks. Cheese, one of the preeminent baseball minds in all of fantasy sports and a winner of a $1,000,000 1st-place prize on both DraftKings and FanDuel, is here to give you his musings on the upcoming MLB DFS slate.

Happy Monday! For this Memorial Day, the sites decided to run completely different main slates. Like, not even kind of close. DK is starting early with a 7-game day slate beginning at 1:10 PM ET. Meanwhile, FD is moving their main slate all the way back to 6:10 PM ET with a 5-game slate. What I’m going to do here is just write up each slate separately. I’ll start with the 7-game DK slate, and then after I get the smoker warmed up, I’ll come back and add in analysis for the 5-game FD slate. Then, I’ve got this massive weapon-shaped thing called a Tomahawk steak that I am going to attempt to cook.

There is one game on the DK slate that we’ll need to pay attention to on the MLB weather page. That would be CIN/KC, but for now, it is included in my analysis as if it plays. And we’ll also have some Expert tags and analysis in our MLB DFS optimizer, LineupHQ, for the later 4-game slate on DK that starts at 7:05 PM ET. Then we will have apple pie.

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Monday Early Slate Pitching: MLB DFS Picks on DraftKings

We have a pretty clear top tier of five pitchers and then a very steep drop-off to everyone else in MME-leftover territory. If there was no salary cap, my pool — even for 150 lineups — would be these top five and no one else.

TOP TIER PITCHING

• Garrett Crochet at Brewers – 28.7% K , 8.1% BB, 1.98 ERA, 3.20 SIERA
• Jacob deGrom vs. Blue Jays – 27.7% K, 5.4% BB, 2.33 ERA, 3.07 SIERA
• Clay Holmes vs. White Sox – 23.2% K, 8.8% BB, 3.13 ERA, 3.71 SIERA
• Kevin Gausman at Rangers – 24.4% K, 5.3% BB, 4.03 ERA, 3.49 SIERA
• Jameson Taillon vs. Rockies – 19.1% K, 5.2% BB, 4.13 ERA, 4.12 SIERA

Garrett Crochet projects as the top pitcher based on his strikeout ability, and while I certainly get it, I can also tell you that Jacob deGrom is my SP1. The matchup is slightly better for Crochet, adding to why he should be higher owned than deGrom. It’s all very close, and my first preference would be just to play Crochet and deGrom together and be done with it. What it comes down to is that I don’t see anything to suggest that Crochet is getting back to last season’s strikeout numbers, which leaves these two at the same level of strikeouts but with deGrom having much better control. In fact, deGrom is well ahead of Crochet in swinging strikes, and since deGrom has settled into his groove, he’s shown the same upside as Crochet. They are both great, either could strike out double-digit batters, and it’s really a coin toss to guess which one has the better start today. When in doubt, I’ll take the ace with better control who is projecting for lower ownership.

The next three are quite tricky. Clay Holmes and Jameson Taillon have the magical matchups against the White Sox and Rockies, respectively, while Kevin Gausman continues to torment game-log watchers with his ups and downs.

It doesn’t really seem like Jameson Taillon fits in this tier, but there is a lot going for him here. Obviously, just the matchup in general is great, and he also gets a good pitching day at Wrigley Field on top of it. The only realistic way the Rockies can do damage is to get some walks and hit home runs. Taillon doesn’t walk a lot of batters, and he gets home run help from the ballpark conditions. With his lower strikeouts to righties and a scary .314 ISO allowed to them this season, I’m still not going to say he’s safe, but it seems more than likely that he manages a quality start here. He’s just enough cheaper than the other top tier pitchers to make it into my primary pool, but I think he’s going to be popular, and I’m going to be under the field.

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