Cubs Face A Wrigley Test That Could Shift Chicago Momentum

As the White Sox and Cubs clash at Wrigley Field, an intriguing lineup decision raises questions while new acquisition Luis Castillo faces crucial pressure to deliver against familiar foes.

The White Sox are keeping things tilted toward the right side Monday night at Wrigley Field.

After sweeping the Detroit Tigers, Chicago heads into the Crosstown matchup with the Cubs and a lineup built to attack left-hander Shota Imanaga. The White Sox are at 65-58, while the Cubs come in at 72-53. First pitch is set for 7:05 CT, with CHSN and WCIU TV carrying the game and ESPN Chicago WMVP 1000 AM on the radio.

Will Venable’s order starts with Chase Meidroth at second base, then Munetaka Murakami at first and Miguel Vargas at third. Randal Grichuk gets the DH spot and bats fourth. He has not homered since June 24, but he has been productive over his last 30 games, hitting .299/.319/.493 in that stretch.

Braden Montgomery, who is in a mini hot streak, follows in the fifth spot. One notable absence is Colson Montgomery, who sits out Monday despite the fact that he has hit better against lefties and is likely getting a scheduled day off.

Tristan Peters is also out, while Brenton Doyle gets the nod in center field. Sam Antonacci stays in the lineup as Venable gives him more chances against southpaws.

Luisangel Acuña and new catcher Jake Rogers fill out the bottom of the order.

Rogers has been solid in a small sample against lefties this year, slashing .261/.333/.435 in 23 at-bats.

The Cubs counter with Pete Crow-Armstrong in center, Seiya Suzuki in right and Michael Busch at first. Alex Bregman bats cleanup, followed by Ian Happ, Nico Hoerner, Pedro Ramírez, Michael Conforto and Carson Kelly.

Luis Castillo is the other big name in this one, and the White Sox need the version they got in his last outing. Since coming over from the Seattle Mariners at the trade deadline, Castillo has already shown both sides of the coin. He was tagged for five runs in four innings against the Boston Red Sox in his first start, then followed that with a gem against the Cincinnati Reds: seven shutout innings, one hit allowed and 10 strikeouts.

Chicago will need the second version if it wants to beat the Cubs.

There’s also some familiarity here. Castillo has seen plenty of this Cubs group from his time with the Reds, and Alex Bregman, Michael Busch, Michael Conforto and Ian Happ have all homered off him in their careers. Nico Hoerner has also had success against him in 11 at-bats.

Imanaga, meanwhile, is coming off seven strong starts after a rougher patch. He owns a 3.74 ERA in 24 starts, and while he has settled in lately with a 2.31 ERA over his last seven, the home run ball has still been an issue. He has allowed 28 this season, and he also gave up seven runs in just three innings in the teams’ last meeting in 2025.

If the ball starts carrying at Wrigley, the White Sox could be in position to make some noise.

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