On October 26, 2025, Chicago’s South Side paused to remember one of the most glorious chapters in its sporting history: the 20th anniversary of the Chicago White Sox’s unforgettable 2005 World Series triumph. For a city and a franchise that had endured an 88-year championship drought, the memories of that dramatic sweep over the Houston Astros still resonate, even as the current team faces a daunting road back to contention.
It’s hard not to get swept up in the nostalgia. The 2005 White Sox were a team for the ages, leading the AL Central from wire to wire and capping their postseason run with a four-game sweep of the Astros to claim Chicago’s first World Series title since 1917. The clincher, a tense 1-0 victory in Game 4 at Houston’s Minute Maid Park, remains etched in the minds of fans who watched Juan Uribe charge Orlando Palmeiro’s slow roller and fire to Paul Konerko for the final out—a moment that instantly erased decades of frustration and futility.
“No matter what ESPN does to minimize or outright ignore the 2005 World Series title, seeing the White Sox reach baseball’s mountaintop can never be forgotten,” one columnist reflected, speaking for a generation of South Siders who had waited a lifetime for that kind of joy. The 2005 season, after all, wasn’t just about winning; it was about overcoming the odds, about a team that played with grit, unity, and a little bit of magic.
Game 4 of that series was a classic pitcher’s duel, with White Sox starter Freddy Garcia and Astros right-hander Brandon Backe matching zeroes for seven tense innings. Early on, both teams squandered scoring chances—Jermaine Dye’s two-out double in the first, Scott Podsednik’s triple in the third, and the Astros’ own threats in the opening frames all came up empty. The tension only ratcheted up in the sixth, when Garcia wriggled out of a bases-loaded jam by striking out Jason Lane, keeping the game scoreless and the Sox’s dreams alive.
It was small ball that finally broke the deadlock. In the eighth, pinch-hitter Willie Harris singled, moved to third on a sacrifice and a groundout, and then dashed home on Jermaine Dye’s sharp single up the middle. That clutch hit not only put the White Sox ahead, it earned Dye World Series MVP honors—an accolade as much for his leadership as for his timely hitting.
The ninth inning was pure drama. Bobby Jenks took the mound, and the Astros threatened to spoil the party. A leadoff single, a sacrifice, and then a foul pop seemingly destined for the seats—until Juan Uribe, in a moment of pure hustle, dove into the stands and made an incredible catch. With two outs, Uribe wasn’t done, charging Palmeiro’s chopper and firing to first just in time. The celebration that erupted was 88 years in the making. The White Sox mobbed the mound, and Chicago’s South Side erupted in joy.
But as the city marks this milestone anniversary, the contrast with the present could hardly be starker. The White Sox are coming off three consecutive 100-loss seasons, including a franchise-worst 121 defeats in 2024—a record for a 162-game season. The hope and swagger of 2005 have given way to frustration and a sense that the franchise is as far from its next title as it’s ever been.
Owner Jerry Reinsdorf, the chairman during the 2005 glory run, is expected to relinquish control of the team, with billionaire Justin Ishbia set to purchase controlling interest by 2029. Many fans see this as a necessary step. “Owner Jerry Reinsdorf must give up control of the team,” wrote one observer, noting that the economics of baseball have shifted dramatically. Where a $75 million payroll was once enough to compete, now it buys only misery. The White Sox are one of just two MLB teams never to hand out a $100 million contract—a reluctance that’s contributed to the current malaise.
General manager Chris Getz, who took over after the 2023 season, has modernized the front office but faces an uphill battle. His first two rosters have lost a combined 223 games, and while a young core is beginning to emerge, the team must add superstar talent and avoid the pitfalls of regression, stagnation, and injuries to have any hope of returning to the postseason spotlight. “What’s harder is proving he is capable of acquiring the player that can win the whole thing,” a columnist noted, capturing the skepticism and cautious optimism surrounding the team’s direction.
Meanwhile, the White Sox’s rotation remains a glaring weakness. Analysts have suggested that the team could look to free agency for short-term upgrades, with 34-year-old Marcus Stroman emerging as a possible target. Stroman, released by the Yankees after a brutal 2025 campaign (6.23 ERA, -0.3 WAR in nine games), could offer veteran innings at a bargain price. “If Stroman can play close to his 2023 self, he’ll be a useful upgrade in the back half of the White Sox rotation,” one report explained, referencing his 1.2 WAR and 3.95 ERA just two seasons prior.
The move would come with little risk, as Stroman’s recent struggles mean he’d command only a modest contract. The alternative, Yoendrys Gómez, posted a 5.17 ERA in 21 games in 2025 and has yet to establish himself as a reliable option. “Signing Stroman wouldn’t be a massive signing for the White Sox, but they’re one of the few teams where it makes sense to give him just one more shot,” the analysis concluded. The key, of course, is not to overpay—a mantra that’s become all too familiar on the South Side.
Looking further ahead, the franchise’s fortunes may hinge on larger structural changes. The impending sale to Ishbia could inject much-needed resources, but the looming specter of a salary cap in the next collective bargaining agreement introduces a new layer of uncertainty. While a wealthy owner could help the White Sox compete under the current system, a cap could level the playing field—and not necessarily in Chicago’s favor. “If a salary cap is somehow put into place, then Ishbia’s excess cash is meaningless because all teams will be on equal financial footing,” one columnist warned, drawing parallels to other long-suffering franchises.
For now, the memories of 2005 remain a beacon—a reminder of what’s possible when talent, timing, and a little luck all come together. The path back to the top is steep, but as Sox fans know better than most, sometimes the impossible just takes a little longer.
As the city celebrates the 20th anniversary of that magical season, hope springs eternal that another parade down 35th Street isn’t another 88 years away. For now, the story of 2005 continues to inspire—proof that, even in baseball, miracles do happen.
