Welcome to The Leadoff, a daily column featuring our top experts’ MLB picks, predictions, and best bets for today’s slate.
With Sean Zerillo making significant changes to the structure of Opening Pitch, we thought we could use another similar daily piece breaking down a few of our favorite bets on the day’s top games.
Each day, Monday through Sunday, one of our top staff members will provide news, notes, and betting analysis on that day’s group of games.
Jon Anderson has that job for Monday, May 25.
MLB Predictions, Picks for Monday, May 25
Follow me in the Action Network App for additional bet notifications.
- Brown Over 5.5 Strikeouts (+114)
- Misiorowski Under 8.5 Strikeouts (-117) | Contreras Over 0.5 Hits (-280)
- White Sox Over 1.5 Team HR | White Sox TT Over 4.5 | Murakami HR | Montgomery HR
- +410 SGP: Schwarber HR & Phillies ML
- Pederson Over 1.5 Total Bases (+164)
- Diamondbacks/Giants Under 7.5 (-108)
- Sheehan Over 6.5 Strikeouts (-126) | Sheehan Over 17.5 Outs (-113)
Cubs vs Pirates Picks
This one gets us started at 1:35 p.m. ET. It's Ben Brownagainst Carmen Mlodzinski in PNC Park. The Cubs are scuffling hard, and they've turned to Brown to fill a void in the rotation. And he's been very good. He has a 30% K% with a 7.5% BB% and a .245 xwOBA allowed in the last three starts since his pitch count really started ramping up. His velo was also up last start to 97.4 on the sinker and 96.7 on the four-seamer.
Brown has a vicious curveball, but he could never get much going for himself because he was super predictable. He threw four-seamers and curves last year. Now, with this sinker, he's much less predictable, and I think it's going to pay off big time for him.
The Pirates have hit right-handed pitching well, but they're missing Ryan O'Hearn right now. Oneil Cruz and Brandon Lowe, among others, offer lots of power upside, but it's a pretty high strikeout rate lineup right now.
I'm betting on Brown here, specifically. I'm not going to pick a winner of the game because the Pirates can get pretty nice outings of Mlodzinski and the Cubs can't seem to hit anything right now.
Pick: Ben Brown Over 5.5 Strikeouts (+114)
Cardinals vs. Brewers Picks
Can the Cardinals end the run of scoreless innings for Misiorowski? He hasn't given up a run since April 25th, when he gave up three against the Pirates. He still struck out nine in that one. The young flamethrower sports a 1.90 ERA and 0.88 WHIP this year with a 39% strikeout rate. It's video game stuff.
And with these kinds of numbers come crazy betting lines. The O/U on the strikeouts is at 8.5 for -109 on the over and -117 on the under. My projection for him is 7.1 strikeouts.
So we can lean into that. It feels dumb to go under on a guy throwing 103 MPH fastballs with a 19% SwStr on the year. But regression is a factor. The Mizz won't stay at a near 40% K% all year, and this line is just too high.
The guy I like to get the offense going for Milwaukee is William Contreras. This matchup with the soft-tossing lefty is perfect for him. Contreras is hitting for a .348 xwOBA against lefties this year with a 91% Zone-Contact%. Liberatore will come right at you, and he's very hittable.
Pick: Misiorowski Under 8.5 Strikeouts (-117) | Contreras Over 0.5 Hits (-280)
Twins vs White Sox Picks
It's going to be hot in Chicago today. This will be Zebby Matthews' first start away from home. And Zebby has been great through two outings this year. Just two runs given up in 13 innings against the Marlins and Astros.
This is a tougher matchup for him. The big problem for Matthews in his big league sample has been home runs. He's a fly-ball pitcher who has gotten hit very hard by lefties. And that's not the kind of problem you want to have against this White Sox lineup. It's a group of hitters who can strike out a lot, no doubt, but they're mashing homers at a very high rate, and they match up very well with Matthews in particular.
Dating back to last year, Zebby has a .359 xwOBA allowed with a homer given up once to every 22 left-handed batters. Munetaka Murakami has a 21% Brl% against righties this year, Colson Montgomery is at 16%.
I think the White Sox are going to do some round-tripping in this one.
Pick: White Sox Over 1.5 Team HR | White Sox TT Over 4.5 | Murakami HR | Montgomery HR
Diamondbacks vs. Giants Picks
Landen Roupp is one of the toughest pitchers to take deep. He's given up just two homers this year, and only one at home. He keeps the ball on the ground, and his stuff moves a lot to make it really tough to square up. Hitters have a .309 xwOBA against him, and he has a decent K% this year at 23%. So I like his chances to survive this Diamondbacks lineup in San Francisco.
Merrill Kellypitches for the Snakes, and he's really hit a groove. Just five earned runs in his last three starts without a walk in his last two. He shook off the slow start, and that changeup is back to doing real damage.
I don't see much run scoring in this one.
Pick: Diamondbacks/Giants Under 7.5 (-108)
Phillies vs. Padres Picks
The Phillies had to travel across the country to San Diego for this game. But they get greeted by a series opener against Randy Vasquez. Vasquez is a right-handed pitcher with a mid-90s fastball and not much else going for him. The Phillies are popping in my matchups model big-time. Schwarber, Harper, and Marsh have historically crushed the type of pitches Vasquez throws, which narrows it down to the specific movement profiles of those pitches.
So I like the Phillies for some loud contact and run scoring today. They're only -126 on the moneyline behind Jesus Luzardo, so that's pretty appealing. The travel and the fact that Luzardo isn't consistent make you pause a little bit there. But I feel good about it.
Let's go with a Schwarber bomb and a Phillies win.
SGP: Schwarber HR & Phillies ML (+410)
Astros vs. Rangers Picks
You know who is hitting the ball pretty well recently? Joc Pederson! He has a .268 xBA and a .375 xwOBA with a 12.5% Brl% in his last 75 PAs. He's looked totally cooked since last season, but he's showing us that there's still some thump in the bat.
The matchup with Imai looks good to my model. Pederson is on the BOOM HITTER list, which identifies the best hitter spots for extra bases.
Imai pitched a lot better last time out, finally finding the strike zone. But so far, it's been bad for him. There's no reason to avoid him with opposing bats.
Pick: Pederson Over 1.5 Total Bases (+164)
Rockies vs. Dodgers Picks
The splits on Emmet Sheehan are pretty wild to see this year. He has a 3.76 ERA at home with a 33% strikeout rate. On the road, it's an ERA of 6.52 with an 18% strikeout rate. That doesn't make much sense to me, and I think it's mostly random.
But there might be something going on there. What’s certain is that this will be his softest matchup of the year. The Dodgers host the Rockies, who have had some really, really awful offensive numbers away from Coors Field the last couple of seasons.
Sheehan is ready to feast in this one.
Pick: Sheehan Over 6.5 Strikeouts (-126) | Sheehan Over 17.5 Outs (-113)
Jon Anderson's MLB Picks and Predictions for Monday, May 25
Follow me in the Action Network App for additional bet notifications.
- Brown Over 5.5 Strikeouts (+114)
- Misiorowski Under 8.5 Strikeouts (-117) | Contreras Over 0.5 Hits (-280)
- White Sox Over 1.5 Team HR | White Sox TT Over 4.5 | Murakami HR | Montgomery HR
- +410 SGP: Schwarber HR & Phillies ML
- Pederson Over 1.5 Total Bases (+164)
- Diamondbacks/Giants Under 7.5 (-108)
- Sheehan Over 6.5 Strikeouts (-126) | Sheehan Over 17.5 Outs (-113)














































