Has Jerry Reinsdorf lost his drive to win?

The state of the Bulls and White Sox is enough to raise questions about his commitment.

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Jerry Reinsdorf has won seven titles — six with the Bulls and one with the White Sox — during his tenure as an owner, but the last came in 2005.

Jerry Reinsdorf has won seven titles — six with the Bulls and one with the White Sox — during his tenure as an owner, but the last came in 2005.

Sun-Times file photo

Watching the two franchises Jerry Reinsdorf owns has been a sad dance. In the last week, the music has gotten maudlin.

The Bulls’ inactivity at the trade deadline was baffling yet unsurprising. The White Sox still are trying to spin their ill-advised signing of Mike Clevinger and hoping Major League Baseball bails them out.

Ordinarily, I don’t like lumping Reinsdorf’s ownership together. It’s not entirely fair because the leagues play by different rules. But considering how his franchises have been performing lately, I’m stuck wondering what drives him.

There’s a quote about Reinsdorf that haunts me. And while I dismissed it on its face when it surfaced, I now wonder whether I didn’t give it enough credence. A few years ago, former Marlins president David Samson was invited on the Le Batard & Friends podcast, ‘‘Mystery Crate.’’ He offered this story about Reinsdorf:

‘‘I was 32 years old, in baseball for my first of 18 years,’’ Samson recalled. ‘‘And [Reinsdorf] said: ‘You know what? Here’s my best advice to you: Finish in second place every single year because your fans will say, ‘Wow, we’ve got a shot, we’re in it,’ but there’s always the carrot left. There’s always one more step to take.’ ’’

Reinsdorf doesn’t recall saying this. His surrogates have denied it happened. I get it. Samson is a provocateur. His work with Le Batard & Friends has been thought-provoking and entertaining, but there always has been a part of me that is skeptical about whether he’s an honest narrator.

The actions of the Sox in the last couple of years and the Bulls this season have me rethinking my position.

My career in Chicago started as the Bulls were winning their fifth and sixth championships. I remember people saying that as much as Reinsdorf enjoyed winning those trophies, they wouldn’t mean as much to him as one World Series for the Sox. In 2005, he got that. They were joyous times, and Reinsdorf cemented himself as the most successful owner in the city.

Since then, luck was the strategy that put Derrick Rose in a Bulls uniform and the Sox haven’t won a playoff series. All of that seems to be OK with Reinsdorf.

Reinsdorf isn’t cheap, but he’s definitely not aggressive. The Sox have had glaring holes in right field and second base for years. The solution always seems to be an inexpensive one.

Right now, a Sox executive is reading this and getting ready to text me where the Sox have ranked in payroll in the last couple of years. They have been in the top 10, but when your scouting and development is lacking a solution, sometimes you’ve gotta throw money at the problem. You would think a franchise that says it’s in a winning window would do everything to maximize that opportunity. Instead, Sox fans got Tony La Russa and a self-imposed budget.

The Bulls are a Rubik’s Cube of problems. After two decades of John Paxson trying to build a champion, ownership moved on. To their credit, the Bulls spent big the last couple of years. The results have been underwhelming. That’s why the fan base was looking for some clarity of action at the trade deadline. Clarity was delivered, and — surprise! — it was status quo.

Fighting for the play-in tournament should be beneath Reinsdorf. His team is five games below .500 and on a four-game losing streak. Yet you look up and see the Bulls are ranked sixth in attendance. If possible play-in revenue is driving decision-making, something truly is wrong.

Have the baseball and basketball operations been hamstrung by budgets? Was Reinsdorf opposed to Steve Cohen buying the Mets because he knew Cohen would spend and make Reinsdorf and other owners look bad? Is the objective of the Bulls and Sox to win? All fair to ask.

What happened to Reinsdorf’s desire to compete? He can’t be happy with how any of this is going, so why is he so reluctant to give his teams the money they need to change the way they operate? If the problem is the people in charge, then make a change. But if you believe in their vision, give them what they need to win. Half-measures lead to mediocre results, but isn’t that what Samson warned us about?

Just good enough ain’t good enough!

You can hear Laurence Holmes talk Chicago sports Monday to Friday from 10 a.m. to
2 p.m. on 670 The Score with Dan Bernstein.

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