MLB Predictions and Moneyline Picks for Memorial Day

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Memorial Day is generally seen as the end of the first quarter of the MLB season, which isn’t entirely accurate, but it serves as a tidy delineation point to help analyze which teams are in the hunt and which ones have work to do.

With 13 games on the slate, I’m eyeing my favorite MLB moneyline picks to cover the entire day of action.

It’s all part of our full MLB picks for Monday, May 25.

MLB moneyline picks for Memorial Day, May 25

Prices courtesy of Polymarket as of 5-24.

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Expert MLB moneyline picks for Memorial Day, May 25

Cubs vs Pirates: Pirates (+100)

Pirates win probability: 49%

Saying the Chicago Cubs have to eventually snap their running eight-game losing streak is true, but using it as a reason to pick them to win any particular game is foolish. Since scoring 10 times in their last win on May 15, the Cubs have plated 23 runs over the eight losses. That’s 2.87 runs per game, and that includes one in which they scored eight! The Pittsburgh Pirates are a bit of a mess, and Ben Brown has pitched well for the Cubs, but I need Chicago’s offense to show me something, anything, before it can regain my trust.

Rays vs Orioles: Rays (-122)

Rays win probability: 55%

The Tampa Bay Rays are an enigma. No one projected them to even be in the race, and here they are leading the AL East in late May. They’ve been demonstrably better than the Baltimore Orioles, who do not have a starter announced. At this number, with Shane McClanahan on the bump for Tampa, there was never an alternative option.

Twins vs White Sox: Twins (-108)

Twins win probability: 52%

Many of these picks will focus on the starting pitcher matchups, and in this case, it’s a matter of favoring Minnesota Twins righty Zebby Matthews over Chicago White Sox left-hander Anthony Kay. Matthews probably should have opened the season in Minnesota’s rotation, and he’s looked sharp in two starts since getting the call. He induces soft contact, doesn’t walk anybody, and probably has more strikeout upside than he’s shown in 13 innings.

Cardinals vs Brewers: Brewers (-194)

Brewers win probability: 66%

I would love to find an angle to confidently take the St. Louis Cardinals in this spot, but Milwaukee Brewers righty Jacob Misiorowski is simply too overpowering to ignore. Cardinals lefty Matthew Liberatore is who he is, and that’s a guy who allows a lot of baserunners and often sees them cross home plate. He’s allowed eight runs over his last two starts, and an early hole will doom St. Louis against “The Miz.”

Yankees vs Royals: Royals (+127)

Royals win probability: 43%

Michael Wacha’s arsenal can give the New York Yankees fits. He has six pitches and can be expected to rely less upon his four-seamer when facing a Yankees lineup that generally crushes heaters. A healthy dose of a rock-solid change, curveball, and slider will keep New York off-balance.

Reds vs Mets: Mets (-156)

Mets win probability: 61%

New York Mets right-hander Nolan McLean is coming off his worst start of the season, allowing eight hits and nine runs (six earned) against the Nats. But with the Cincinnati Reds answering with southpaw Nick Lodolo, McLean has enough of an overall edge in the pitching matchup. I am a huge Lodolo fan, but he hasn’t looked right in three starts since returning from a blister that kept him on the shelf for the first month and change of the season. He issued five walks in his most recent outing, and until he figures out his command, he’s almost an instant fade candidate.

Diamondbacks vs Giants: Giants (-133)

Giants win probability: 56%

Landen Roupp has been one of the lone bright spots for the San Francisco Giants in 2026, boasting a 3.27 ERA and 1.15 WHIP over his 10 starts. He doesn’t generate a ton of whiffs, but he limits hard contact with the best of them while keeping the ball on the ground at a 55.7% rate (94th percentile). This helps him exponentially at Oracle Park. The Arizona Diamondbacks lineup isn’t terrible, but it’s closer to league average (100 wRC+). And while it’s not predictive, it’s encouraging to know Roupp held the D-Backs to one run while scattering seven hits in his last outing on May 19 in Phoenix.

Nationals vs Guardians: Guardians (-170)

Guardians win probability: 63%

Cleveland Guardians right-hander Tanner Bibee is the weirdest pitcher in MLB this season. Somehow, he is 0-6 despite a 3.75 ERA and a generally solid FIP. He’s not an overpowering hurler, and the Washington Nationals have a dangerous offense, but he’s not going to 0-7. I just don’t see Zack Littell keeping Cleveland off the board. The only area where Littell thrives is in his 71st-percentile walk rate, which can be construed as a negative. He lives in the zone, and he gets killed in there.

Phillies vs Padres: Phillies (-113)

Phillies win probability: 53%

Philadelphia Phillies left-hander Jesus Luzardo is the second-weirdest pitcher in MLB this season. His 4.85 ERA is certainly quite poor, but everything under the hood looks solid. He ranks in the 82nd percentile or better in fastball velocity, exit velocity, chase rate, whiff rate, strikeout rate, walk rate, and hard-hit percentage. He’s a buy-low candidate in fantasy baseball and a chief reason why I like the Phillies over the San Diego Padres here.

Astros vs Rangers: Rangers (-133)

Rangers win probability: 56%

I’m tempted to go with the visiting Houston Astros here with no starting pitcher officially announced for the Texas Rangers, but I don’t yet trust Tatsuya Imai (8.31 ERA, 16.9% walk rate, four home runs allowed in 17 1/3 innings), and Yordan Alvarez may either miss the game or be limited in the wake of back spasms that forced him to leave Saturday’s game early.

Marlins vs Blue Jays: Blue Jays (-163)

Blue Jays win probability: 61%

Trey Yesavage has been a breath of fresh air for the Toronto Blue Jays since getting healthy, going 2-1 with a microscopic 1.07 ERA and a 28.7% strikeout rate in 25 1/3 innings. It’s a small sample size, but with the Miami Marlins traveling north after a finale against the Mets in South Florida, I expect the Blue Jays’ bats to get the job done against Janson Junk while Yesavage holds serve.

Note: While Vladimir Guerrero Jr. did exit Sunday’s game after being struck by a pitch, he’s optimistic about playing against the Marlins. I still like Toronto if Vladdy doesn’t play, but we might get a better number if he sits.

Rockies vs Dodgers: Rockies (+233)

Rockies win probability: 28%

We have a couple of things working against us up front, all of which can be summed up with it’s the Colorado Rockies visiting the Los Angeles Dodgers. But that’s more or less baked into the line, and we’re not going to touch the Dodgers at -270. L.A. starter Emmet Sheehan has been up and down over his nine starts, and his 4.93 ERA can be explained away by an elevated 1.77 HR/9. This is all about value, recognizing Sheehan as the Dodgers’ most vulnerable starter, who even a dismal Colorado offense can squeak out some runs against.

Mariners vs A’s: A’s (+104)

A’s win probability: 48%

The Seattle Mariners are deploying starter Luis Castillo as an opener in front of Bryce Miller in the latest gambit to get the veteran right. So far, nothing’s worked, as he’s 1-5 with a 6.41 ERA in 46 1/3 innings, and the numbers under the hood aren’t much better. The A’s, notably Nick Kurtz and Shea Langeliers, will feast on Castillo early at Sutter Health Park in what could be a laugher.

Odds are correct at the time of publishing and are subject to change.
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