Bears vs. White Sox: rebuild fantasies and realities

In which we talk about Caleb Williams

On May 9, 2016, the White Sox beat the Rangers to improve their record to 23-10. A season that we went into without a lot of optimism seemed like it might be turning into a pleasant surprise. At 13 games up, you could arguably go .500 the rest of the way and make the playoffs.

That didn’t happen. The season fell apart, almost immediately. By the end of June the White Sox were worse than .500, and a tentative, struggling era was over.

Coming out of that disappointment, over two days in December the Sox traded Chris Sale and Adam Eaton, and received Yoán Moncada, Michael Kopech, Lucas Giolito, Dane Dunning, and Reynaldo López. This was the beginning of a new core. We knew it would be a few bad years, but there were promises of October fireworks. While a World Series is never guaranteed, the Sox were setting themselves up for years of contention.

That also didn’t happen; at 6-25 here in 2024, we know with teleological certainty that the rebuild was a failure. The end result was two playoff wins that did nothing to mask absolute organizational incompetence and a rot deep within Jerry Reinsdorf’s franchise. The present was a bust, and any lingering good vibes from 2005 have receded into an unimaginable past.

Organizational incompetence? Deep, family-based rot? A team clinging onto the faded glories of an increasingly sepia-stained past?

Does anyone hear the faint tone of “Bear Down, Chicago Bears” in the background?

And yet … the Bears now have hope. Great trades, key signings, and an inspiring draft have positioned the Bears to be a genuinely good team.

What did they do right — and what did the Sox do wrong? The differences are extremely telling.

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Extremely Important Caveat No. 1!

Now, you might be saying, but the Bears haven’t actually won anything yet! They were 7-10 last year, with some historic collapses. They have a rookie quarterback, a coach that frequently seemed outmatched, and a defense that was prone to letting teams come back against them. And, well, they are the Bears.

It’s true that the future isn’t written. Even teams that do everything right can fall apart. Football is an incredibly, maybe overly-complex game, and even incredibly well-built teams like the Bills can spin their wheels and eventually fall apart with little playoff glory to show for it.

So there’s nothing that says the Bears are going to be successful. And as excited as long-time fans are, longtime fans also know that this is where talented quarterbacks go to die. But that leads us to our first primary difference with the Bears rebuild.

Difference No. 1: Forgetting the Past

As the book says, you might be done with the past, but the past ain’t done with you. Both the White Sox and the Bears have, historically, not ever been done with the past, but instead reveled in it.

The Bears have always built themselves around a strong defense and a powerful running game. That’s how we’ve defined ourselves as fans as well. Big linebackers, strong running backs. Just like in 1985! Remember 1985! And while an stout defense is important, the idea that there has to be a “Bears” way to do things is silly, and is increasingly silly in today’s NFL.

Ryan Poles said nuts to all that. Over the last couple of years, he’s accumulated offensive weapons styled around the modern NFL game. It hasn’t been perfect (Chase Claypool, anyone?) but it revealed a GM who wasn’t beholden to some irrelevant history. His team was built to win in today’s game.

The Sox have a Sox way of doing things. It isn’t going without stars — the 2005 team had Paul Konerko, Jermaine Dye, A.J. Pierzynski, José Contreras, and other All-Star caliber players. But in that year, the stars played like stars, and the role players played like stars. There was no need to spend big, since everyone played to like their 99th percentile.

And that’s been “the Sox way” ever since. The entire rebuild was centered around hoping that the (potential) stars would stay healthy and live up to their potential, and then a bunch of scrubs could catch fire and carry us to the World Series. The Sox Way was more important than the correct way.

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Extremely Important Caveat No. 2!

Football and baseball are (be sure you are sitting!) different sports. They are built differently in the draft and through free agency, and have completely different depth structures. In football, a generational quarterback can paper over some flaws (though not forever). In baseball, you can have Mike Trout and Shohei Ohtani, and still be the Angels.

Obviously, there can be no 1 x 1 comparisons. But the way that teams should be built in the sports have some crossover.

Difference No. 2: Filling the Gaps

The Bears were lacking in game-changing wide receivers. They had a rough offensive line. They had solid defensive players (Khalil Mack, Roquan Smith) who were contractual burdens.

What did the front office do? They focused on the line. They made the painful decisions to lose Mack and Smith. They traded a No. 1 pick for DJ Moore and another draft pick (which ended up a No. 1 pick). They signed Keenen Allen. They drafted Rome Odunze. In other words, they looked at what they needed to do … and did it.

The Sox? Not as much. For years — years! — everyone (everyone!) knew we lacked a right fielder and second baseman, yet those spots were never filled. Not with big-name free agents, not through smaller-name free agents, not in trades, not ever.

Instead, they took “baseball players” and thought, well, if you can play one position, you can play anywhere. That’s how we’ve had Gavin Sheets and Leury García in right field in key situations. We acquired a ton of 1B/DHs without having a plan for how to use them. It was embarrassing, self-defeating, and undercut the entire rebuild.

It would be like if the Bears just drafted a bunch of centers and said, hell, the kid can play football, they could probably be a safety. Maybe a running back?

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Extremely Important Caveat No. 3!

I AM NOT PRAISING BEARS MANAGEMENT I AM NOT PRAISING BEARS MANAGEMENT I AM NOT PRAISING BEARS MANAGEMENT I AM NOT PRAISING BEARS MANAGEMENT

Also not Cubs management.

Difference No. 3: Management Getting Out of the Way

The Ricketts suck. Dear sainted Virginia aside, the McCaskeys suck. But both of them made the decision that they would take care of business things and let the sports people take care of the sports side of the portfolio. For the Ricketts, that ended up in their dual dreams of a World Series and turning a vibrant city neighborhood into an unremarkable suburb.

The McCaskeys have never gotten out of their own way; the owner’s dad literally invented the league, after all. But in recent years, there has been a clear divide between the business side of the Bears, with Kevin Warren handling the real estate portion, and Poles and staff being allowed to take care of football.

Is the business/real estate side gross? Of course! But does it benefit the team where there is a clear distinction. Absolutely.

The Sox? Jerry Reinsdorf hired his old buddy to manage a young, exciting team and wrecked the rebuild, then handpicked the least-qualified general manager in baseball because it was easier than having to pay someone else. You can’t define the rot in the White Sox better than that.

Are the Bears going to win the Super Bowl? Look, I’ve been burned a million times. I was all-in on Justin Fields. And I thought for sure this White Sox team would be the most exciting few years of my baseball life. I thought Derrick Rose would win us multiple championships. I know sports don’t work the way you think, and every season ultimately ends in disappointment unless everything goes right.

Look at the Bills. Look at the Padres. Look at all the teams and their sad fans who thought that this time, this time it will be different, only to end up feeling like suckers, broken upon the shoals of reality. That’s sports.

That said, fuck yeah, we’re winning the Super Bowl. Caleb, baby!!! SUPER BEARS SUPER BOWL.

That’s sports, too.