White Sox vs. Cubs Prediction, Odds, Probable Pitchers and Prop Bets for Friday, May 16

Iain MacMillan | May 16, 2025

The White Sox are big underdogs against the Cubs in the first game of this week's Crosstown Classic. / Peter Aiken-Imagn Images

The first Crosstown Classic of 2025 is set to take place this weekend as the Chicago White Sox head across the city to take on the Chicago Cubs at Wrigley Field.

The first game will take place on Friday afternoon and as you might expect, the Cubs are significant favorites. With that being said, are the White Sox worth a bet? I'm here to argue exactly that. Let's dive into it.

White Sox vs. Cubs Odds, Run Line, and Total

Odds via FanDuel Sportsbook

Run Line

• White Sox +1.5 (-108)
• Cubs -1.5 (-111)

Moneyline

• White Sox +188
• Cubs -225

Total

• 12.5 (Over -115/Under -105)

White Sox vs. Cubs How to Watch

• Date: Friday, May 16
• Game Time: 2:20 PM EST
• Venue: Wrigley Field
• How to Watch (TV): Marquee Sports Network, CHSN, MLBN (out-of-market only)
• White Sox Record: 14-30
• Cubs Record: 25-19

White Sox vs. Cubs Probable Pitchers

• White Sox: Shane Smith, RHP (1-2, 2.08 ERA)
• Cubs: Cade Horton, RHP ( 1-0, 6.75 ERA)

White Sox vs. Cubs Best Prop Bet

• Lenyn Sosa OVER 1.5 Total Bases (+115)

One of the few bright spots of the White Sox offense has been Lenyn Sosa, who has a .267 batting average on the season and has recorded 2+ hits in four of his last five games. This seems like a great opportunity at plus-money to bet on him to record at least two bases on Friday afternoon.

White Sox vs. Cubs Prediction and Pick

In today's edition of Walk-Off Wagers, I broke down why I'm backing the White Sox as big underdogs at Wrigley Field:

Call me crazy, but I think +188 is a great price on the White Sox in this spot. They'll be rolling with Shane Smith as their starter, who has been a pleasant surprise for them this season. He has a strong 2.08 ERA and 1.085 WHIP in eight starts this season and if he can string together another impressive start, he's going to give the White Sox a chance to win.

He'll face off against Cade Horton, who allowed three earned runs in his 4.0 innings he pitched in his first appearance this season. I firmly believe the White Sox have the advantage in the starting pitcher category.

It's also worth noting the Cubs' offense has cooled off a bit compared to their hot start to the season. They're just 17th in OPS over the past two weeks. That's enough to leave an opening for the White Sox to win this one as significant underdogs.

Pick: White Sox +188

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