Caleb Wilfinger
The second half of the 2025 MLB season continues rolling along, and Monday features an 11-game slate of action for us to enjoy. I’m 81-57-1 on my MLB best bets this year and the Pickswise MLB handicapping team as a whole is currently on a 24-11 run! Let’s keep it going as we get into today’s top MLB predictions on Monday, September 8.
You can also find out our MLB picks for EVERY GAME today.
MLB best bet: Boston Red Sox -1.5 over Athletics (-125)
Odds available at DraftKings Sportsbook at time of publishing. Playable to -130.
For my first MLB best bet today, we’ll focus on this AL matchup between the Red Sox and Athletics from Sacramento. Boston has been up and down of late, but it’s hard to ignore backing the Red Sox with Garrett Crochet on the mound. The young ace is coming off his worst outing of the year by a considerable margin, but most of that damage came in one single inning — which gives me confidence in Crochet’s ability to bounce back from a disappointing result. While he’ll be going up against a sneaky good Athletics offense, Crochet should get some much-needed run support from his offense against Luis Morales (4.13 xERA) and the A’s bullpen. All things considered, I’ll lay the wood with the better team in this one.
MLB best bet: Seattle Mariners -1.5 over St. Louis Cardinals (+100)
Odds available at FanDuel Sportsbook at time of publishing. Playable to -110.
For my second MLB best bet on Monday, we’ll target the Mariners to win by at least 2 runs over the Cardinals. Seattle has been up-and-down of late, but I love the matchup the Mariners have against Miles Mikolas (5.46 xERA, bottom 5% whiff rate, strikeout rate and barrel rate) — a pitcher whom I have consistently faded all season to profitable results. As for the home team, Seattle is countering with Bryan Woo — who holds a 3.02 ERA and has surrendered more than 3 earned runs just once over his last 9 outings dating back to July. Woo is terrific at avoiding walks and generating strikeouts, and he should thrive against a Cardinals lineup that ranks 27th in slugging and 24th in OPS for the season. Let’s back Seattle to roll at home.
