White Sox vs. Guardians MLB picks: Surging Cleveland could take first place in AL Central on Monday

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The White Sox and Guardians are going in opposite directions entering Monday's big game

Sep 14, 2026 at 9:43 am ET • 4 min read

The first game of Monday around MLB is also probably its most important as the first-place Chicago White Sox open a huge AL Central series at second-place Cleveland. They are definitely headed in opposite directions of late, and I'd guess this series winner does capture the division.

At DraftKings, 59% of handle and 66% of bets are on Cleveland -155, while 97% of money and 69% of wagers are on Over 7. Looks like a beautiful night by the lake: Mainly clear. Low 57F. Winds ESE at 10 to 15 mph. Bet $5+ on any of Monday's games and get $200 in bonus bets when you bet at DraftKings Sportsbook:

The surprising Pale Hose (76-73) had been leading the Central comfortably for a while, but they have started crashing back to earth and hold a half-game edge. The Guardians (76-74), meanwhile, are one of those clubs that always seems to "wake up" at the right time of the season, and that has occurred. They have a roster chock full of guys with experience in big games/series like this.

However, Chicago leads the season series 6-4 and thus would have to get swept in these three to lose that tiebreaker as this set concludes it. The team that doesn't win the Central may well earn the AL's third wild-card spot --- the Yankees and Red Sox will take the first two – and the Guardians currently hold it by a game over Toronto. For any playoff spot, they are -180. 

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White Sox vs. Guardians MLB same-game parlay

• Cleveland to not bat bottom 9
• Under 1.5 first-inning runs
• Alt Under 10.5

DraftKings SGP price: +167 (subject to change)

Frankly, this is all gravy for the White Sox (-500 for playoffs), as they are a year ahead of schedule in their rebuild. Manager Will Venable's team had a win total of only 67.5 in the spring. Venable is the -190 favorite for AL Manager of the Year, and deservedly so. Chicago has massively surprised offensively thanks in large part to rookies Munetaka Murakami, Tristan Peters and Sam Antonacci. The pitching staff is starting to develop major cracks, though.

Trade deadline acquisition Luis Castillo was supposed to stabilize that group but has been a bust. The entire rotation has been an issue since the team hit a high-water mark of nine games over .500 on Aug. 29 with a victory in the Twin Cities. Veteran lefty Sean Newcomb (2.4, 2.77 ERA) gets the start tonight but won't come close to qualifying for a win as he's a pseudo-opener with a season high of 3.0 innings.

Newcomb has been lousy in four August appearances at 0-1 with a 9.95 ERA in 6.1 innings. But he has a 1.23 ERA this year in six outings spanning 7.1 innings against Cleveland. Right-hander Sean Burke (8-7, 3.58 ERA) is expected to follow him as the bulk guy. Perhaps Burke's starting confidence is shaken after getting hammered for seven runs and eight hits in 1.1 innings of a usual start last time out vs. Pittsburgh. 

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Cleveland has been a completely different team since a 1-0 home loss to San Francisco dropped the Guardians to 61-66 and 5.5 games out of the Central lead and into third place. Should we really be surprised by the late turnaround? The franchise did the same thing in 2025 to chase down Detroit and win the Central. Sadly, I expect the Guardians the win the division now even as +145 underdogs. Experience matters.

"Last year helps a lot because we had the huge comeback," said utility man David Fry entering this matchup. "But it doesn't really matter who we're playing because we're in the division and the wild card, so every win is big."

One of my favorite AL pitchers to back (at home anyways) goes tonight in righty Gavin Wiliams (13-7, 3.78 ERA, plus-$466). He is working off back-to-back quality starts, both at Progressive Field, with a 1.38 ERA this month, and has struck out double-digit batters in eight of his past 11 overall.

Williams' turn was originally to be Saturday, but the Guardians wanted to give him a bit more rest for this big opener. He has not gotten a decision in three 2026 starts against Chicago and has a 4.11 ERA and .232 OBA over 15.1 innings. Miguel Vargas, a huge part of Chicago's season success, has good splits off him at 5-for-12 with a homer.

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Seems like every edge belongs to the home side, including hand-picking the starting pitcher and a pretty rested bullpen after Sunday's blowout win at the Twins. Check out other expert picks in the SportsLine daily newsletter.