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Chicago White Sox vs New York Yankees Prediction and Picks - September 23, 2025

By: Dean Whitaker Published 09/23/2025, 07:30 AM ET
Aaron Judge looks to lead the Yankees over the White Sox

Major League Baseball action on Tuesday evening, and we have a Chicago White Sox vs New York Yankees Prediction ready to rock and roll. It has been a very rough year for the White Sox, who come in with the 2nd worst record in the league at 58-98. The Yankees currently own the top Wildcard spot in the American League but they still have their sights set on the AL East, sitting just two game behind the Jays. Read on to see our White Sox vs Yankees prediction.

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White Sox Staring Down 3rd Consecutive 100 Loss Season

The White Sox dropped their home finale on Sunday, falling 3–2 to the Padres despite a late push in the seventh inning. Sean Burke allowed three runs (two earned) over four innings, and the offense was held to just five hits. Chicago’s only scoring came via bases-loaded walks to Miguel Vargas and Andrew Benintendi, highlighting the team’s ongoing struggle to generate runs through contact. With 98 losses on the season, the Sox are staring down a third consecutive 100-loss campaign, and their margin for error is razor-thin with six games remaining.

Now heading to the Bronx, the White Sox begin a three-game set against a Yankees team still chasing the AL East crown. Chicago has gone just 2–8 over its last 10 games and owns a dismal 33–48 road record. The lineup has been inconsistent, though Lenyn Sosa and Chase Meidroth have shown flashes of production in recent weeks. Defensively, errors continue to haunt them—two more on Sunday pushed their season total to 94. The pitching staff has been stretched thin, and the bullpen has struggled to hold leads, making early run support a critical factor if they hope to compete.

Shane Smith will start for Chicago, entering with a 6–8 record and a 4.06 ERA across 135.1 innings. He’s struck out 129 and held opponents to a .220 batting average, relying on a mix of sliders and changeups to keep hitters off balance. Smith has been more effective on the road than at home, and he’ll need to be sharp against a Yankees lineup that’s been punishing mistakes. His ability to navigate the top of the order—especially Judge and Bellinger—will likely determine how deep he can go.

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Yankees' Magic Number Is Five

The Yankees return to the Bronx riding high after a dramatic 7–1 extra-inning win over the Orioles on Sunday. Rookie Ben Rice delivered the knockout blow with a grand slam in the 10th inning, while Jazz Chisholm Jr. added a solo homer and Anthony Volpe chipped in with an RBI single to cap a six-run outburst. Cam Schlittler pitched 5.1 innings of one-run ball, and the bullpen combined for 4.2 scoreless frames, continuing a dominant stretch that’s been key to New York’s late-season surge. The win gave the Yankees three of four in Baltimore and kept them just two games behind Toronto in the AL East.

With six games remaining, the Yankees hold the top AL Wild Card spot and are firmly in control of their postseason destiny. Their magic number to clinch a playoff berth is 5, meaning any combination of Yankees wins and losses by trailing teams that adds up to five will secure their spot. They’ve gone 10–5 over their last 15 games and have leaned heavily on a balanced lineup and elite bullpen depth. Ben Rice has emerged as a clutch bat, driving in five runs on Sunday and raising his season total to 62 RBIs. Aaron Judge continues to anchor the offense, while Cody Bellinger and Trent Grisham provide left-handed power and defensive versatility. The infield defense has tightened up, and the Yankees have been executing well in late-game situations.

Luis Gil gets the start Tuesday, entering with a 4–1 record and a 3.42 ERA over 76 innings. The hard-throwing righty has struck out 88 while walking 31, and he’s been especially tough on right-handed hitters, holding them to a .198 average. Gil mixes a high-90s fastball with a sharp slider and occasional changeup, and he’s shown the ability to pitch out of jams with poise. Against a White Sox lineup that’s struggled to make solid contact and has been prone to chasing, Gil has a chance to dominate early and give the Yankees a strong start to their final homestand.

Chicago White Sox vs New York Yankees Pick

White Sox vs Yankees Moneyline Pick

  • White Sox +1.5 (4 Units)

White Sox +1.5 over the Yankees is a sharp value play for Tuesday night, especially with Shane Smith on the mound against Luis Gil. Smith has quietly delivered quality starts in 3 of his last 5 outings, and while his ERA sits at 4.21, he’s shown improved command and strikeout efficiency against power-heavy lineups. The Yankees lead MLB in home runs and slugging, but they’ve also struck out 9.0 times per game, ranking 28th in plate discipline. If Smith can keep the ball down and limit long-ball damage, Chicago’s bullpen—despite its volatility—has held opponents to just 2.8 runs per game over its last six outings. That gives the White Sox a path to stay within a run even if they don’t pull off the upset.

Offensively, Chicago has struggled overall, but they’ve shown flashes against right-handed pitching, and Luis Gil has been inconsistent in recent starts—allowing 13 hits and 7 earned runs over his last 9.1 innings. The Yankees have covered the run line in just 6 of their last 10 games, and with a total set at 8.5, oddsmakers are projecting a tighter contest. Lenyn Sosa and Andrew Benintendi have both hit safely in four of their last five games, and if the White Sox can scratch out early runs, they’ll force New York into a more aggressive bullpen rotation. With Gil’s volatility and Chicago’s ability to manufacture runs late, the +1.5 offers solid value in a game that could easily finish 5–4 or 4–3 either way.

White Sox vs Yankees Over/Under Pick

  • Under 9 (5 Units)

Under 9 in Tuesday night’s Yankees–White Sox matchup is a sharp lean given the pitching setup and recent scoring trends. Luis Gil has held opponents to a .237 batting average and owns a 3.33 ERA, while Shane Smith has quietly delivered three quality starts in his last five outings. Both teams have leaned on their bullpens effectively—Chicago’s relief corps has allowed just 2.8 runs per game over its last six, and New York’s staff ranks top-10 in strikeouts per nine. Offensively, the White Sox rank 26th in runs scored and 29th in slugging, while the Yankees have hit the Under in seven of their last ten games. With cooler weather and two capable starters on the mound, this one profiles as a 5–3 or 4–2 finish—making the Under 9 the sharper side.

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