White Sox vs. Yankees Prediction, Odds, Probable Pitchers and Prop Bets for Wednesday, Sept. 24

The Yankees are massive favorites on Wednesday night.

New York Yankees designated hitter Aaron Judge is a great prop target on Wednesday. / Tommy Gilligan-Imagn Images

The New York Yankees clinched a playoff spot with a win on Tuesday night, and they’re just one game out of top spot in the AL East heading into Wednesday’s game against the Chicago White Sox.

Chicago is 41 games under .500 this season, and it’s set as a massive underdog in New York against Yankees lefty Max Fried, who has a 2.92 ERA in 2025. 

Fraser Ellard (4.50 ERA) will get the ball as an opener for the White Sox in this matchup. Chicago’s bullpen hasn’t been terrible (4.05 ERA this season), but can it hold down a Yankees lineup that is No. 1 in MLB in runs scored and OPS in the 2025 season?

Oddsmakers don’t seem to think so. 

Here’s a breakdown of the odds, players to watch in the prop market and my prediction for this American League battle on Wednesday. 

White Sox vs. Yankees Odds, Run Line and Total

Odds via DraftKings Sportsbook

Run Line

• White Sox +1.5 (+138)
• Yankees -1.5 (-169)

Moneyline

• White Sox: +294
• Yankees: -385

Total

• 8 (Over -115/Under -105)

White Sox vs. Yankees Probable Pitchers

• Chicago: Fraser Ellard (0-2, 4.50 ERA)
• New York: Max Fried (18-5, 2.92 ERA)

White Sox vs. Yankees How to Watch

• Date: Wednesday, Sept. 24
• Time: 7:05 p.m. EST
• Venue: Yankee Stadium
• How to Watch (TV): YES, CHSN
• White Sox record: 58-99
• Yankees record: 89-68

White Sox vs. Yankees Best MLB Prop Bets

Yankees Best MLB Prop Bet

• Aaron Judge OVER 1.5 Total Bases (-125)

There isn’t a team in MLB with a better OPS against left-handed pitchers like Ellard than the Yankees, and Judge leads the way with a 1.221 OPS against lefties this season.

The reigning AL MVP is hitting .375 with five home runs over the last two weeks, and I think he’s a great bet to get to this White Sox pitching staff on Wednesday. Judge has 170 hits and 120 walks in the 2025 season, leading MLB in batting average, OPS, OBP and slugging percentage. 

Of his 170 hits, a whopping 80 have gone for extra bases. I think that makes the Yankees star an easy target to pick up two or more bases on Wednesday, especially since he’ll be facing a lefty in his first at-bat. 

White Sox vs. Yankees Prediction and Pick

Look, bettors are going to have to lay some juice if they want to back the Yanks in this one, but it’s hard not to trust New York in this spot with Fried on the mound.

Not only are the Yankees right back in the mix to win the AL East, but they have dominated when Fried gets the ball, winning 21 of his 31 starts. Of those 21 wins, 18 of them have come by two or more runs this season.

Meanwhile, the White Sox are just 25-51 on the road, and they’ve dropped nine of their last 10 games overall. 

New York should be able to roll in this matchup, especially with how Fried has pitched as of late. After some struggles in August, the lefty has a 2.05 ERA in four starts in September, tossing at least seven innings in three of those outings. The Yankees have won all four of those starts.

I’ll back New York to cover the run line and remain in the mix for the AL East title this season. 

Pick: Yankees -1.5 (-169 at DraftKings)

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Odds refresh periodically and are subject to change.

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