Chicago’s South Side was on top of the world on this day, 20 years ago.

The club completed one of the most impressive regular season and postseason runs ever, sweeping the Houston Astros to capture Chicago’s first World Series title since 1917.

Eighty-eight years of misery were history the moment Juan Uribe charged Orlando Palmeiro’s chopper and threw to Paul Konerko for the final out of a 1-0 Game 4 victory:

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. It was an accomplishment many Sox fans went to their graves never seeing. So, while the four-letter network prefers to romanticize the 2004 Boston Red Sox or the 2016 Chicago Cubs breaking their curses, the 2005 White Sox deserve a special place in the annals of baseball history.

The Pale Hose led the AL Central wire-to-wire. The South Siders won the ALCS with four starting pitchers throwing complete games — a feat that will never happen again. Then, the White Sox swept an Astros team that featured ace pitchers Roger Clemens, Andy Pettitte and Roy Oswalt.

Fast forward to the present, and the franchise is at rock bottom.

The team has had three straight 100-loss seasons for the first time in club history. During that stretch, the team set the record for most defeats in a 162-game season with 121 losses in 2024.

The White Sox are just as far away from their next title as they are from 2005’s run to championship glory.

Getting the White Sox back on top feels akin to wondering when humans will go back to the moon: You know it can be done. It is just a matter of taking on the challenge again.

Conditions that must be met
Owner Jerry Reinsdorf must give up control of the team. It is ironic that this must happen, as he was the chairman when the franchise won it all in 2005.

However, the economics have changed for him to ever own a team that can win it all. A $75 million payroll in 2005 was the 12th highest in baseball; a payroll like that today produced a 100-loss season for the White Sox.

Twenty years ago, $100 million contracts existed, but they were still reserved for the very best in the game. Now a $100 million deal is reserved for 2.0 WAR players or better.

The White Sox are still one of two MLB teams never to hand out a contract that large. That has helped lead to this franchise slowly decaying into its current rotten state. Reinsdorf was never willing to spend the money it took to take advantage of the competitive window that started at the beginning of the decade.

Thankfully, billionaire Justin Ishbia has an agreement with Reinsdorf to purchase controlling interest as soon as 2029.

Hopefully he is a rich, hobbyist owner ready to unleash his deep pocketbook to acquire elite talent and build an infrastructure that can develop it. Remember, spending in free agency is not always the solution; drafting effectively and doing well in international free agency while developing those players into major-leaguers is the backbone of a good organization.

Still, having Ishbia function like the Los Angeles Dodgers ownership would go a long way toward the White Sox winning another World Series.

Having the person in place to acquire great talent — whether through the draft, international free agency, trades or general free agency — is another condition that must be met.

Right now, general manager Chris Getz has put together two rosters that have lost 223 games (121 in 2024, 102 in 2025). The team may be its current state of losing because of his predecessors, and to his credit Getz’s front office overhaul has modernized how the franchise operates.

But that was the easy part. What’s harder is proving he is capable of acquiring the player that can win the whole thing.

The one positive aspect about the 2025 season is that a core has emerged that the team can move forward with. However, more superstar talent must be added before the team can start being considered a contender. Also, regression, stagnation and injuries must be avoided for this current rebuild to produce a championship.

Then there is navigating through all the variances that October baseball figuratively throws at a club as impediments to winning a championship. The 2005 White Sox are proof of how many things have to go right to win it all: El Duque getting out of that bases-loaded jam in Boston to help secure a win in Game 3 of the ALDS, the A.J. No-K in Game 2 of the ALCS, and little-used Geoff Blum hitting the go-ahead home run in extra innings of Game 3 of the World Series.

Finally, it is unknown if Ishbia’s billions will make a difference once he takes over, as no one has any clue what the next collective bargaining agreement will look like. Owners are going to fight for a salary cap in the next CBA. The hope is it will control costs and create parity. However, I do not think a salary cap will benefit the White Sox. Salary caps can still prevent teams from coming close to a championship. The Chicago Bears are nowhere close to snapping their 40-year championship drought. The New York Jets are still chasing their first Super Bowl appearance since 1969.

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. However, the current financial system will provide an advantage to the White Sox once Ishbia takes over, as he would be one of the wealthiest owners in the game. Although let’s hope he is a better majority owner than his brother, Mat, is for the Phoenix Suns.

So many factors must be met to win a championship. That is why it is hard to definitely say the White Sox will win another World Series. At the very least, you just have to hope it does not take another 88 years to win another World Series on Chicago’s South Side.