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The first edition of the 2024 Crosstown Classic begins Tuesday as the White Sox limp into Wrigley Field looking to snap an 11-game losing skid.

Things haven’t been much better for the Cubs, who have lost 14 of their last 19 matchups and are now in third place in the NL Central and a half-game back of the final wild-card berth.

The White Sox are big underdogs in Game 1 of the series as Chris Flexen (5.50 ERA over 54 innings) takes on Shota Imanaga (1.86 ERA over 58 innings).

Here’s a betting preview of Tuesday night’s matchup at Wrigley Field.

White Sox vs. Cubs odds

  • Moneyline: White Sox + 240, Cubs -300
  • Run Line: White Sox +1.5 (+120), Cubs -1.5 (-145)
  • Total: Over 9.5 (-105), Under 9.5 (-115)

Odds via BetMGM

White Sox vs. Cubs prediction

Maybe pitching on 11 days rest didn’t agree with Imanaga, or maybe it was the tough matchup versus a strong Brewers lineup in batter-friendly conditions. Either way, the sensational Japanese star had the worst outing of his young big-league career in his last start, as he allowed eight hits and seven earned runs in only 4 1/3 innings of work.

Imanaga will have a great opportunity to get right Tuesday versus a White Sox team that owns putrid splits versus left-handed pitchers this season. The White Sox own a wRC+ of just 71 against lefties, with an OPS of only .598. They have hit to a wRC+ of onlt 83 against lefties over the last 30 days.

The White Sox could get one key bat back Tuesday as Luis Robert could return to the lineup after serving as DH with Triple-A Charlotte on Sunday. Still, they will feature a lengthy list of absences that includes Andrew Vaughn, Eloy Jimenez, Andrew Benintendi and Yoan Moncada.

The White Sox could get Luis Robert back on Tuesday.
The White Sox could get Luis Robert back on Tuesday. (Nuccio DiNuzzo/Getty Images)

Imanaga has pitched to an xERA of 3.01 and an xFIP of 3.46. He holds a Stuff+ rating of 93 and a Location+ rating of 105.

Imanaga has a first pitch-strike rate of 69% this season, which is the fifth-highest mark among qualified starters in MLB. He has also gotten batters to chase 35.9% of the time. Working in pitcher-friendly counts while featuring excellent chase and whiff rates has allowed him to achieve a stellar 5.90 K/BB ratio.

Flexen struggled to a 6.86 ERA last season, and while a big part of that number was pitching for Colorado, he does not look to be a far superior pitcher in 2024. He owns a Stuff+ of 55 and a Location+ rating of 97, which are both worse than his 2023 marks. He has allowed a .597 slug rate on pitches inside the strike zone since the start of the last season.

Flexen has pitched to an xFIP of 4.83 in 2024 and has seen his K/BB ratio trend down to 1.91.

With no key bats on the IL anymore, the Cubs project as a fairly tough matchup for Flexen. Over the last 30 days, they have hit to a wRC+ of 101 against right-handed pitching.

White Sox vs. Cubs pick

This series could provide a little extra juice for both of these struggling sides to snap out of an ugly stretch of play.

The Cubs hold a ton of significant advantages in this specific matchup with Imanaga on the mound and have a great opportunity to grab a comfortable win.

Pick: Cubs run line -1.5 (-140 at bet365 and Caesars)



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