October 31 has delivered a strange mix of White Sox history over the years - from tragedy, to award races, to a World Series spotlight, to a managerial hire that pointed the franchise in a new direction.
The earliest note on the date comes from 1937, when Ed Arthur Walsh, the son of White Sox Hall of Famer Ed Walsh, died of rheumatic fever after falling into a coma at his childhood home in Meriden, Conn. He was 32.
The younger Walsh never fully escaped his father’s name, but he carved out a real athletic résumé of his own. At Notre Dame, he made the football team as a punter under Knute Rockne and went 18-6 pitching for a Fighting Irish baseball team managed by his father.
The White Sox signed him after graduation in 1928, and he reached the majors that same season, debuting on the mound on July 4. Walsh spent four seasons with the club and finished with an 11-28 record, a 5.57 ERA and 0.1 pitching WAR.
He was gone from the game just five years after his final big league appearance, while his father lived until the White Sox pennant-winning season of 1959, 22 years later.
Another October 31 memory belongs to one of the great Cy Young races in White Sox history. In 1972, Gaylord Perry narrowly beat Wilbur Wood for the AL honor, 64 votes to 58.
The numbers were close enough to make the vote sting for White Sox fans. Wood actually threw 34 more innings, started nine more games and logged three more shutouts.
Perry, though, had the cleaner run prevention line, with a 1.92 ERA to Wood’s 2.51, along with advantages in ERA+ and WHIP. Perry also finished just ahead in WAR, 10.8 to 10.7, and placed sixth in AL MVP voting to Wood’s seventh.
What made the result harder to take was the team context. Perry’s Cleveland club finished sixth in the AL East at 72-84, while Wood’s White Sox were 87-67 and ended up second in the AL West. Had Wood won, he would have become just the second White Sox pitcher ever to take home a Cy Young, joining Early Wynn from 1959, and he would have paired with Dick Allen as a major award winner for the 1972 club.
Fast forward to 2005, when the White Sox were in the middle of their run to their first World Series title in 88 years. Sports Illustrated put Scott Podsednik and his game-winning home run from Game 2 on the cover, with the headline: “World Series.
In A Match Up Of Two Title Hungry Teams, The White Sox Struck First, Dramatically Downing The Astros In Games 1 And 2.” The next week, though, the magazine barely acknowledged the championship at all, giving the Sox only a small circle photo of the celebration in the corner of the cover.
The main feature was Peyton Manning and Tom Brady, previewing a regular-season NFL game.
Then came 2011, when former White Sox manager Tony La Russa announced his retirement three days after guiding the Cardinals to another World Series title. He would not stay retired.
Most recently, on Oct. 31, 2024, the White Sox officially introduced Will Venable as the 44th manager in franchise history. Venable arrived from the Rangers, where he had served as associate manager under Bruce Bochy and helped Texas win the 2023 World Series. Before that, he coached in the Red Sox and Cubs organizations after nearly a decade as a big league outfielder.
The reaction to the hire was strong, and for good reason. Venable was viewed as one of the game’s rising names, and he stepped into what many saw as the toughest job in baseball after the White Sox lost a record 121 games in 2024. The move was followed by a 19-win improvement in 2025 and another 24 wins in 2026.
That same day, the White Sox also bought out Yoán Moncada’s contract for $5 million instead of paying him $25 million for the 2025 season. Moncada’s White Sox tenure never matched the promise that came with his reputation as the overall No. 1 prospect in baseball, and he is commonly viewed as a bust. Still, the raw value tells a different story: he was paid $71.1 million during his White Sox career and produced 14.5 WAR, which works out to $4.9 million paid per WAR - a slight bargain for the club.
In Other News...
White Sox Just Got An Early 2027 Reality Check
After a 24-win jump from 2025 to 2026 and a return to the postseason for the first time in five years, the White Sox had reason to feel like the rebuild was finally turning into something sturdier. The next step, though, is proving that last season was not just a one-year spike, and the early 2027 conversation already has a cautionary tone around Chicagos place in the league.
ESPNs first pass at the 2027 landscape put the White Sox 13th, a reminder that the market is still waiting to see whether this roster can hold its ground. The concerns are familiar for a team trying to stay on the rise: pitching depth needs attention, and the offense still has to clean up the strikeouts that can flatten an otherwise promising lineup. The offseason is going to matter here, because Chicago is trying to do more than repeat what it did in 2026, it is trying to make sure that progress actually sticks. [Read more 🡒]
White Sox First Offseason Move Could Shape Their Next Core
The White Sox have made their first notable offseason move by hiring Matt Roffe as their new scouting director, a job that puts him in charge of an area that has to hit for a club trying to rebuild its next core. He takes over for Mike Shirley, who left earlier in the year, and the hire signals that Chicago is treating talent evaluation and the draft as a priority rather than a background task.
Roffe arrives with a reputation for helping sharpen a scouting operation, coming from Milwaukee after serving as its assistant director of domestic scouting. His background includes involvement in one of the Brewers more notable recent draft successes, and the White Sox are clearly betting that kind of eye for value can help them uncover the next wave of players who fit their timeline. [Read more 🡒]
Will Venable Just Gave The White Sox Rebuild Another Huge Test
Will Venables first season steering the White Sox through the rebuild did more than steady the ship. Chicago took a meaningful step forward under his leadership and reached the AL Division Series in 2026, a sign that the organizations long reset is starting to produce real traction rather than just hope. The progress has shown up beyond the dugout, too, with Chase Meidroth, Munetaka Murakami, Sam Antonacci, Tristan Peters and Miguel Vargas all drawing award consideration after the season.
Now Venable is in position to get some individual recognition of his own, which only adds another layer to the White Soxs turnaround story. For a club trying to prove its rebuild is arriving on schedule, the managers place in the league-wide conversation matters almost as much as the wins themselves, and the next round of voting will tell whether Chicagos rise has caught the attention of the rest of the sport. [Read more 🡒]