White Sox take 2-0 ALDS lead as Venable's team closes in on first ALCS since 2005

The Chicago White Sox, managed by Will Venable, will host the Cleveland Guardians in Game 3 of the American League Division Series on Wednesday, October 7, with a chance to reach the AL Championship Series for the first time since 2005. Chicago won 4-3 in Cleveland on Monday to take a 2-0 lead in the best-of-five series. For a team that set a modern MLB record with 121 losses in 2024, one more win would mark an extraordinary postseason advance.

The White Sox have won all four of their games this postseason, each on the road, according to MLB's Game 2 account. Their next game is at Rate Field in Chicago, where a victory would end the series. A fourth game is scheduled there for Thursday if Cleveland extends it. Chicago has put itself in position to clinch, but it has yet to do so.

How Chicago won Game 2 in Cleveland

Cleveland scored twice in the first inning on Monday. MLB reported that Chicago had not trailed in its first 27 innings of the 2026 postseason before the Guardians took that lead. The White Sox recovered in the sixth: rookie Braden Montgomery hit an opposite-field double that scored two runs and put Chicago ahead 3-2, then Chase Meidroth drove in another run with a single.

Sean Burke gave Chicago 5 1/3 innings in relief, allowing one run and one hit while striking out six and walking one, according to MLB. Closer Grant Taylor secured the 4-3 result with a 1 1/3-inning save. MLB noted that Taylor had also pitched four innings in Saturday's Game 1, making his contribution across the two games unusually substantial for a closer.

What Venable brought from Princeton basketball

Venable's account of his approach reaches back to Princeton, where he played basketball from 2001 to 2005 while also earning All-Ivy honors in baseball. The Guardian reported that he was a first-team All-Ivy basketball player, reached the NCAA Tournament and once scored 21 points against Duke. He later spent eight years in the major leagues, mostly with the San Diego Padres.

Venable told the Guardian that basketball taught him to pay attention to spacing, timing and small details. He connected those lessons to positioning, movement before a pitch and timing at the plate. The Guardian described Chicago's postseason pitching as a collective, matchup-driven approach, with pitchers used in shorter stretches rather than a fixed sequence built around a long start. Those are Venable's explanation and the newspaper's analysis of his methods; the results cannot be assigned to any single tactic.

His manner has also shaped how players describe the team. Designated hitter Andrew Benintendi told the Guardian that Venable is ‘the same guy every single day,’ calling him steady and even-keeled. Venable credited players working together and for one another rather than presenting the turnaround as his achievement alone. He also praised Montgomery's confidence in a major playoff moment; Montgomery, in turn, said he valued his manager's trust.

From 121 losses to an ALCS opportunity

The scale of Chicago's change is clear in its recent record. MLB reported that the White Sox lost their 121st game of 2024 on September 27, setting the modern-era single-season losses record. The Guardian reported that the club finished that year 41-121, won 60 games in 2025 and improved to 84-78 in the 2026 regular season, one game behind Cleveland in the AL Central. Venable took over a club still losing heavily and has described the improvement as an organizational effort that includes general manager Chris Getz's plan.

The White Sox last reached the ALCS in 2005, the year they won the World Series. MLB's historical figures favor teams in Chicago's position: clubs with a 2-0 lead in a best-of-five postseason series have advanced 83 times in 93 attempts. Division Series teams that won their first two road games under the current 2-2-1 format advanced 17 times in 19 attempts. Those records describe past series; Chicago still needs to win one of the remaining games against Cleveland.