The White Sox have touched them all since 2000, hitting it out of the park with a World Series title in 2005, striking out looking with a modern-day record for losses in 2024 and pulling off too many “in all my years watching baseball there’s something I’ve never seen” moments in between. Jerseys shredded by a protesting All-Star pitcher’s pocketknife, the unforeseen and controversial return of Tony La Russa, an unsolved stadium shooting and Drake LaRoche all made back-page headlines in between.
There were just five postseasons — four of them one-and-done bow-outs — one owner, four general managers and seven managers.
Here are the 25 most significant moments in the last 25 years:
25. Oct. 3, 2000
A 95-67 record and an American League Central title sent “The Kids Can Play” Sox to the AL Division Series, where Mariners manager Lou Piniella psyched out reliever Keith Foulke with an unusual on-field visit with Mike Cameron on first base in the 10th inning of Game 1 at Comiskey Park. Cameron stole second a pitch later, and Edgar Martinez and John Olerud homered, fueling a 3-0 sweep.
24. July 24, 2022
Minnie Minoso was inducted into Hall of Fame. “Mr. White Sox” and the “Cuban Comet,” a seven-time All-Star who broke the Sox’ color barrier in 1951 as the first Black Hispanic player, entered the Hall of Fame after being elected by the Golden Days Era Committee. He was the first Sox player elected since Harold Baines in 2019.
23. Sept. 16, 2007
Jim Thome walked off the Angels and right-hander Dustin Moseley with a ninth-inning pinch home run to center field, the 500th of his 612 career homers. Acquired from the Phillies in a deal for center fielder Aaron Rowand after the 2005 World Series, Thome rounded first base with his fist above his head and was mobbed at the plate before being carried off the field by teammates Jermaine Dye and Bobby Jenks. The Sox traded Thome to the Dodgers during the 2009 season.
22. Oct. 29, 2013
Cuban first baseman Jose Abreu signed an international record-breaking six-year, $68 million deal. The Sox outbid the Red Sox, Giants, Marlins, Astros and Rangers with money well spent as Abreu won the AL MVP in 2020 while receiving votes in six other seasons. In nine seasons with the Sox, Abreu batted .292/.354/.506 with 243 home runs — third in franchise history — 863 RBI and an .860 OPS. He ranks in the top five on the Sox’ all-time list in homers, RBI, hits and doubles.
21. April 13, 2009
Jermaine Dye and Paul Konerko hit their 300th career homers back-to-back against Tigers pitcher Zach Minor. Dye led off the second inning and Konerko followed to give the Sox a 2-0 lead in a 10-6 victory in Detroit. Both players had been World Series heroes, Dye taking MVP honors and Konerko belting five homers in the postseason, including two in the World Series. Konerko hit his 400th homer April 25, 2012, at Oakland, a tying shot in the ninth inning. His 432 homers rank second to Frank Thomas (448) on the Sox’ all-time list.
20. Aug. 25, 2023
The Sox’ ballpark has been the scene of bizarre and criminal incidents, including the mindless attack of Royals first-base coach Tom Gamboa by a father and son, both shirtless, on Sept. 20, 2002. But a mysterious shooting in the bleachers that remains unsolved might top them all. A 42-year-old woman was hit in the leg and a 26-year-old woman suffered a graze wound to her abdomen when they were struck by gunfire during the fourth inning of a game against the Athletics. The Sox and Chicago police were criticized for allowing the game to be completed, although a concert after the game was canceled. The 42-year-old woman filed a lawsuit against the Sox and the Illinois Sports Facilities Authority last August, claiming they failed to enforce a stadium prohibition on firearms and protect attendees from foreseeable dangers. She’s seeking more than $50,000 in damages, personal injuries and losses. The Sox insist the shots were fired outside the ballpark.
19. Oct. 7, 2005
In possibly the most memorable relief-pitching performance in franchise history, Orlando Hernandez replaced Damaso Marte with the bases loaded and no outs in the sixth inning of Game 3 of the ALDS at Fenway Park, protecting a 4-3 lead. Jason Varitek and Tony Graffanino (10-pitch at-bat) popped out, and Johnny Damon struck out. The Sox went on to win 5-3 and complete a three-game sweep en route to an 11-1 postseason and a World Series title. Hernandez was 9-9 with a 5.12 ERA in 24 games (22 starts) that season.
18. April 14, 2021
A year after right fielder Adam Engel preserved Lucas Giolito’s no-hitter against the Pirates in an empty Guaranteed Rate Field during the COVID-19 year, left-hander Carlos Rodon tossed the 20th no-hitter in Sox history. Hitting the Guardians’ Robert Perez with a pitch on the foot with one out in the ninth was all that prevented Rodon from recording the Sox’ fourth perfect game.
Rodon, who had come back from Tommy John and shoulder surgeries, had been non-tendered by the Sox the previous offseason and signed for $3 million. He would go 13-5 with a 2.37 ERA, helping the Sox win the AL Central, despite dealing with shoulder fatigue in the second half. But the Sox didn’t extend him an $18.5 million qualifying offer after the season, costing them a compensatory pick. Rodon then signed a six-year, $162 million deal with the Yankees. In 2012, Philip Humber pitched one of the most unlikely perfect games, blanking Hall of Famer Ichiro Suzuki and the Mariners in Seattle. He finished the year with a 6.44 ERA and was finished in baseball at age 30 after posting a 7.90 ERA with the Astros the next season.
17. March 15, 2016
Adam La Roche, citing family reasons, walked away from the Sox during spring training, igniting national attention and debate about kids in the workplace. LaRoche’s 14-year-old son, Drake, was an everyday presence and had a locker in the clubhouse. While he was welcomed by most teammates, he was on the back fields too much for vice president Ken Williams’ liking. When Williams asked LaRoche to “dial it back,” LaRoche, who was also dealing with back problems, quit baseball, walking away from $13 million. Teammates, including ace left-hander Chris Sale, backed LaRoche and said they didn’t mind having Drake around.
16. Nov. 29, 2023
A beloved broadcaster locally and nationally, Homewood’s very own Jason Benetti was enjoying a good run as Hall of Famer Ken Harrelson’s play-by-play replacement with a smart, passionate and entertaining voice alongside analyst Steve Stone. But when his relationship with the Sox soured — saying he felt disrespected by vice president for marketing Brooks Boyer while failing to captivate chairman Jerry Reinsdorf — Benetti was let out of his contract and jumped to the Tigers, adding to the Sox’ record-setting losses on the field. The Tigers embraced it as a major coup.
Meanwhile, with little major-league broadcasting experience, Jon Schriffen was hired as the replacement. While the team plummeted to 121 losses in 2024, Schriffen struggled on the broadcasts. The Sox’ booth plunged from sixth to 30th in Awful Announcing’s rankings.
15. July 27, 2014
Frank Thomas became the first Sox player inducted into the Baseball Hall of Fame in his first year of eligibility, garnering 83.7% of the vote. He was the AL MVP in 1993 and ’94 and the Sox’ all-time leader in home runs (448), RBI (1,465), runs scored (1,327), doubles (447), on-base percentage (.427) and slugging percentage (.568). Thomas played 19 seasons with the Sox (1990-2005), Athletics (2006, ’08) and Blue Jays (2007-08), hitting .301 with 521 homers, 1,704 RBI and a .974 OPS in 2,322 games.
The Big Hurt’s No. 35 was retired by the Sox in 2010, and his likeness was unveiled as a statue at U.S. Cellular Field in 2011. A fractured foot prevented him from playing in the World Series. His last game with the Sox was July 20, 2005. After the season, the Sox let him go by not offering arbitration. With a chip on his shoulder, Thomas finished fourth in AL MVP voting and led the Athletics to an AL West title.
14. May 20, 2006
The Cubs-Sox city rivalry intensified thanks to interleague play, and no game stands out more than the Sox’ 7-0 triumph at the Cell, punctuated by A.J. Pierzynski flattening Cubs catcher Michael Barrett on a play at home in the second inning.
Pierzynski’s slap of the plate as he scored accentuated the organization’s disdain for their North Side rival. Barrett punched Pierzynski in the face, the benches and bullpens of the two contending clubs emptied and Tadahito Iguchi delivered the knockout blow two batters later with a grand slam against Rich Hill. “Punch A.J.” became the marketing cry for write-in All-Star votes, and Pierzynski beat out Twins rookie pitcher Francisco Liriano for the final AL spot in internet voting. “Maybe it was the wrestling vote that got me over the top,” Pierzynski said.
13. Oct. 16, 2005
Jose Contreras beat the Angels in Game 5 of the AL Championship Series, sending the Sox to their first World Series since 1959 and completing a feat likely never to be repeated: Four consecutive complete games, with Mark Buehrle, Jon Garland, Freddy Garcia and Contreras winning 2-1, 5-2, 8-2 and 6-3 decisions.
A.J. Pierzynski caught all four games, and his wily, successful attempt to reach first on a phantom trapped third strike by Angels catcher Josh Paul with two outs and nobody on in the ninth inning of Game 2 — one of the most controversial and perhaps biggest umpiring gaffes in postseason history — was arguably the turning point of the series.
12. Oct. 12, 2020
Manager Rick Renteria guided the Sox through three rebuilding years, then took them to a postseason berth in the abbreviated 2020 season, finishing 35-25 before losing to the Athletics 2-1 in the wild-card series. General manager Rick Hahn said the move wasn’t about Renteria’s performance but “taking the next step,” and while he had former Astros manager AJ Hinch in mind, Reinsdorf had other ideas, hiring 76-year-old Tony La Russa out of retirement. La Russa’s Hall of Fame pedigree notwithstanding, it was a stunning move considering La Russa’s age and a recent drunk-driving charge. Reinsdorf, who for years lamented La Russa’s firing by the Sox in 1986, said it was about having the best man for the job.
11. July 23, 2016
In perhaps the most bizarre moment in franchise history, five-time Sox All-Star left-hander Chris Sale, vehemently protesting having to wear the loose-fitting, pajama-like, 1970s “South Side Hitmen” throwback uniform on a night he was scheduled to pitch, cut up almost every jersey hanging at players’ lockers before a game against the Tigers.
Sale, who was sent home and suspended five games, later said the Sox cared more about promotions than winning. Sale knew something about winning. He was 74-50 with a 3.00 ERA and 1,244 strikeouts in seven seasons with five consecutive top-six finishes in Cy Young voting in a normal Sox uniform before he was traded that December to the Red Sox, for whom he helped win the 2018 World Series. Perhaps Sale had a point.
10. Aug. 5, 2023
Down goes Anderson! And down goes the rebuild. Tim Anderson squaring off like a prize fighter and getting decked by a Jose Ramirez right cross was the snapshot of a falling star, distraught by family issues and an early-season knee injury that affected his hitting.
Under first-year manager Pedro Grifol, general manager Rick Hahn’s pick to replace Tony La Russa, the Sox were backpedaling in lockstep with their former energizer en route to 101 losses. An All-Star the previous two seasons and the bat-flipping face of the franchise’s “Change the Game” marketing campaign, Anderson batted .245/.286/.582 with one homer in 524 plate appearances in 2023, and his $14 million option for 2024 was declined.
9. July 23, 2009
Left-hander Mark Buehrle, one of the most popular Sox players ever, threw his second career no-hitter, this one in perfect-game fashion, before 28,036 on the South Side. Buehrle joined Jim Bunning, Addie Joss, Sandy Koufax, Randy Johnson and Cy Young as the only pitchers to throw a no-hitter and a perfect game.
Shortly after broadcaster Ken Harrelson famously implored viewers to “call your sons, call your daughters,” Dewayne Wise, inserted by Ozzie Guillen in center field before the ninth, leaped above the wall to take a home run away from Gabe Kapler, clutching the loose ball with his bare hand on his way down.
8. Nov. 3, 2003
In an upset, Ken Williams passed on hiring the favorite to replace manager Jerry Manuel, former Blue Jays skipper Cito Gaston, and named former Sox three-time All-Star shortstop Ozzie Guillen, the Marlins’ third-base coach, after Williams and Reinsdorf were captivated by Guillen’s interviews. It was the beginning of a stormy, colorful and often successful relationship that brought a World Series title in Guillen’s second season but would not end well in 2011.
On Sept. 26, 2011, Guillen’s turbulent — especially in his later years with Williams — but never dull eight-year stay as manager came to an end after Reinsdorf declined to give the extension Guillen asked for and let him out of his contract. Guillen, who was 678-617 with five winning seasons and two playoff appearances with the Sox, immediately went to the Marlins, who gave the Sox two players as compensation. Pitching coach Don Cooper managed the last two games.
Guillen lasted one year in Miami. He was fired after enduring a 69-93 season and a five-game suspension for making complimentary comments about Cuban leader Fidel Castro, and he hasn’t managed since. He’s approaching his seventh season as an entertaining pregame and postgame analyst on Sox TV broadcasts.
7. Dec. 6, 2016
Five months after his July declaration that the Sox were “mired in mediocrity” hanging around the .500 mark, Hahn kicked off a dramatic rebuild at the winter meetings, trading Chris Sale to the Red Sox for prospects Yoan Moncada, Michael Kopech, Luis Basabe and Victor Diaz. At the same meetings, he pried Lucas Giolito, Reynaldo Lopez and Dane Dunning from the Nationals for Adam Eaton.
In 2017, Jose Quintana went to the Cubs for Eloy Jimenez and Dylan Cease, and 19-year-old Cuban prospect Luis Robert Jr. was signed to a $26 million bonus. Hahn (and Williams) were lauded around baseball for the deals, which would ultimately lead to just two playoff appearances, both ending after one round.
6. Aug. 12, 2021
Arguably the pinnacle moment of the shortstop’s career, Tim Anderson’s two-run blast into the Dyersville, Iowa, corn against Yankees lefty Zack Britton gave the Sox an 8-7 victory in the “Field of Dreams” game and an 11½-game lead over the Guardians and Tigers in the AL Central. “These are the moments you want to be in,” said Anderson, who hit one of the eight homers in the game. “These big games like this, this is the time to show up.” Jose Abreu tied Harold Baines on the Sox’ homer list in the first, and Eloy Jimenez and Seby Zavala also went deep.
5. Aug. 22, 2023
As general manager and assistant GM, Ken Williams and Rick Hahn brought the 2005 World Series title to the South Side, but Jerry Reinsdorf put their run to an end while the Sox were closing in on 101 losses under second-year manager Pedro Grifol’s watch. Williams and Hahn’s terminations were announced in a news release from Reinsdorf before a 6-3 loss to the Mariners at Guaranteed Rate Field, a surprising move despite the record because of Reinsdorf’s well-known loyalties. Williams, he said, “was like a son.”
“Ultimately, the well-worn cliche that professional sports is results-oriented is correct,” Reinsdorf said. “While we have enjoyed successes as an organization and were optimistic heading into the competitive window of this rebuild, this year has proven to be very disappointing for us all on many levels.”
“At my inaugural presser, I spoke of winning multiple championships,” Williams said. “That was my goal, our goal, and we failed. I am a bottom-line guy, and the bottom line is we didn’t get it done. This is what happens as a result.”
Reinsdorf named director of player development and assistant GM Chris Getz as his new GM on Aug. 31, saying a hire from within would speed up the recovery process. A year later, Grifol was fired, and entering Getz’s second full season, the Sox seem farther away from contending than ever.
4. Sept. 30, 2008
Pitching on three days of rest, John Danks held the Twins to two hits in eight innings, Jim Thome led off the seventh with a 460-foot home run to center field and 40,354 fans, almost all dressed in black, went nuts watching the Sox (89-74) win 1-0 in the AL Central tiebreaker that will forever be known as the “Blackout Game” in Sox lore. Michael Cuddyer crashed into Pierzynski, who held on to 38-year-old Ken Griffey Jr.’s throw from center in the fifth to preserve a scoreless tie. The Sox would lose to the Devil Rays 3-1 in the ALDS, one of the club’s four playoff appearances since 2000.
3. Oct. 23, 2005
The World Series warrants 25 moments of its own, but three home runs stood out: two in Game 2 at U.S. Cellular Field — Paul Konerko’s two-out grand slam in the seventh inning that gave the Sox a 4-2 lead and Scott Podsednik’s walk-off in the ninth — and Geoff Blum’s tiebreaker in the 14th of Game 3. Buehrle, after taking his spikes off and enjoying a couple of beers, laced the spikes back up and pitched the 14th for the save, two nights after throwing 100 pitches in Game 2. Juan Uribe picked up a grounder, and first baseman Konerko gloved it for the final out. He gave the ball to Reinsdorf at the victory parade. The Sox set an attendance record the next year.
2. Sept. 27, 2024
The Sox’ 4-1 loss to the Tigers in Detroit was their 121st of the season, breaking the 1962 expansion Mets’ modern-day record for defeats. The season was lowlighted by an AL-record 21-game losing streak. Fans wore bags over their heads, often chanted “Sell the team” at Reinsdorf and, hoping to see history, supported visiting teams when the Sox were within reach of the dubious record. One of the team’s only bright spots, All-Star lefty Garrett Crochet, was traded at the winter meetings as second-year GM Getz proceeded with the organization’s second rebuild in less than 10 years. Will Venable was hired after the season to be the team’s fourth manager in six seasons.
1. Oct. 26, 2005
Capping a dominant 11-1 run in the postseason, the Sox defeated the Astros 1-0 at Minute Maid Park to complete a four-game sweep and claim their first World Series title in 88 years.
Days later, their first World Series championship parade started at U.S. Cellular Field and made its way to a rally downtown.