The Chicago White Sox have never actually tried to contend

After the Chicago Cubs won the World Series, Chicago White Sox General Manager Rick Hahn had a clear message for owner Jerry Reinsdorf.

If the White Sox wanted to win a World Series, they needed to tear it all down. Trade away their superstars. Sign international prospects. Tank for draft picks. Save money now, then spend it when the youth was ready to contend.

Gone were the days of signing a core of free agents for $200 million (unless you’re the Los Angeles Dodgers, of course). It worked.

After years of trying to win with the 2005 World Series core and continually falling short of the playoffs, the Sox needed a change in philosophy and approach.

The seasons between the 2005 World Series and the 2016 World Series had been the same thing. Sign an All-Star bat past or late in their prime and convince the fans that an AL Central title or Wild Card spot was attainable. The truth is, it never was.

That all changed after the Cubs won it all. They shipped off the core for a plethora of young prospects and just like that, the Chicago White Sox were on a clear path to being a playoff contender.

Don’t let the rebuild fool you, the Chicago White Sox never actually tried to contend.

Fast forward to 2020 when the prospects had finally arrived on the South Side. It was time to start getting excited for October baseball at 35th and Shields. There was one thing that was missing though and that was a veteran core.

For the Cubs on the other side of town, everything truly came together in the 2015 offseason. The club signed postseason ace Jon Lester and poached former All-Star OF Jason Heyward from the hated St. Louis Cardinals. Finally, they were true World Series contenders.

It wasn’t just a young core that brought the title to the North Side in 2016. It was a mix of talented youth combined with postseason and veteran experience. That’s one thing that the Chicago White Sox are missing. And it seems as if they don’t care.

It’s become quite clear that the White Sox never actually wanted to take the steps to win a World Series. And yet here we are, the 2022 offseason in the rearview mirror and the Sox front office refuses to make any significant changes to the roster.

They’ve been open about not wanting to make a splash in free agency. Let’s call it how we see it here. This White Sox front office has not changed since 2006. They’re still stuck in the same mentality that they had coming off of the 2005 World Series championship.

This team will continue to rot in purgatory until there’s a true regime change. They’ve never changed from the Kenny Williams school of one more $20 million contract.

This is the same organization whose largest contract in TEAM HISTORY is a $75 million deal for an outfielder who had hit .274 in his career prior to a bounceback year in 2022.

Whether or not it was clear to Rick Hahn at the time, Reinsdorf and Kenny never actually planned on spending money. They saw an opportunity to tank, save money and continue to refuse to spend.

At this point, the championship window is inching ever so closer to being shut. All-Star and franchise leader Jose Abreu is gone, the club continues to refuse to spend, and the prospects aren’t getting any younger.

If it’s not too late already, now is the time for Reinsdorf to open up the checkbook and make a splash in free agency. Build up a seasoned, veteran rotation to help out the young starters, add another bat or two, and run for October.