Ricky Dimon
A new week in Major League Baseball gets underway with a modest 9-game slate on Monday. It includes Blue Jays vs Rays, Reds vs Cardinals, Rangers vs Astros and Phillies vs Dodgers. The Pickswise team is on an 32-16 run in this MLB best bets series. Let’s build on that momentum and hopefully deliver some more winners today!
Make sure you also check out our MLB picks for every game on Monday, September 15.
MLB best bet: Chicago Cubs ML over Pittsburgh Pirates (-126)
Odds available at Bet365 Sportsbook at time of publishing
With the occasional exception, I am happy to fade Pittsburgh whenever Paul Skenes is on the mound. Monday is not one of those exceptions. The Pirates stink, and they are a horrendous 1-8 in their last 9 games. Braxton Ashcraft is getting the start and he is basically a long reliever. The right-hander has made 23 appearances this season (6 starts) and has never logged more than 5.2 innings. He has worked more than 3.0 innings only 3 times. That does not bode well for a Pittsburgh team that is sporting a 4.06 bullpen ERA. The Pirates’ last 5 losses have all come by 1 run, and they have used a ton of relievers in lots of high-leverage situations throughout these close contests. That kind usage is a recipe for disaster heading into this matchup.
The Cubs are more than capable of taking advantage. Whereas Pittsburgh has long since been eliminated from postseason contention, Chicago isn’t going to catch Milwaukee in the National League Central, but it still has everything to play for as it tries to wrap up the #1 wild card and secure home-field advantage in a first-round series. The Cubs have won Jameson Taillon’s last 3 starts, during which he has allowed just 4 runs in 15.1 innings.
MLB best bet: Baltimore Orioles ML over Chicago White Sox (-142)
Odds available at FanDuel Sportsbook at time of publishing
The other club from Chicago, on the other hand, is going nowhere fast. Nobody in Major League Baseball other than the Rockies is even close to as bad as the White Sox (57-93). They had had actually been playing decent baseball in September but are now coming off a 3-game sweep at the hands of Cleveland, during which the crossed the plate a grand total of 3 times. Speaking of sweeps, the Sox are 0-3 against the Orioles so far this year.
Head-to-head dominance should continue for Baltimore in this series opener. The O’s are going with Kyle Bradish, who has impressed in 3 appearances since returning from Tommy John surgery. Bradish has a 2.65 ERA, 0.94 WHIP and a 21-to-4 strikeout-to-walk ratio in 17.0 innings. The White Sox are countering with Sean Burke, who is 4-10 with a 4.35 ERA and 1.47 WHIP a strikeout-to-walk ratio worse than 2-to-1 (115 Ks, 58 BBs). Chicago lost his previous outing against Baltimore in 2025 and will likely do the same on Monday.
