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An Open Letter to Jerry Reinsdorf

Updated: Aug 11, 2023

Dear Mr. Jerry Reinsdorf, owner of the Chicago White Sox and Governor of the Chicago Bulls,

The time has come for you to sell both of these historic franchises.

You have owned both of these teams during some incredible years for both these teams. The Jordan dynasty, MVP Derrick Rose with the Bulls, and the incredible 2005 season for the White Sox. But both of these teams haven't been relevant since those periods in time, and it all comes down to your penny-pinching ways as an owner.

I'll start with your ownership of the Chicago White Sox first. This past off-season, you signed the highest-paid free agent in White Sox history, Andrew Benintendi, to a five-year-75 million-dollar contract. You have owned the White Sox since 1981, and that's the highest free-agent contract you're willing to pay out? While the south side doesn't have the allure or prominence of the Cubs to the north, Chicago still should be a free-agent destination. It would be one thing if Benintendi were a star or an above-average player to earn that contract. The problem is that the former Royals outfielder is playing like a bench player, with a wins above replacement (WAR) of just 0.5. According to FanGraphs, a WAR of 2.0 is good enough for an average full-time position player, while anything between 0 and 1 is good for average bench players.

The south siders also have only cracked the top 15 in the league in payroll four times in the past ten seasons on Opening Day. Before 2023, 2022, and 2021, the last time the Sox were in the top 15 in spending was 2015, with only four players making over 10 million dollars as they went a mediocre 76-86, good enough for 4th in the division. Meanwhile, your cross-town rival Chicago Cubs made an NLCS appearance, and your division rival Royals won the World Series that same season.

Over your entire tenure as owner, the White Sox have only made the playoffs seven times. Seven times in 41 years, and with the current rate the 2023 team is on, it will look to be seven times in 42 seasons. Since the World Series title, Guaranteed Rate Field has only seen the playoffs twice, as the team has gone 1,303-1,401 (.482) during that span. After making the playoffs in 2020 and 2021, it marked the first time in franchise history that the team made the playoffs in consecutive seasons. They have come close several times, but the fact that it took a shortened COVID season and then finally living up to potential in 2021 to do so after 41 years of ownership and nearly 130 years of existence is just downright sad.

Now your team, which had expectations of winning the division coming into 2023, has completely imploded. As of this writing, the White Sox sit 4th in the weak AL Central at 45-68, 5 games back of the for third Tigers and 14 games back of the Twins for first place. It's not even the record and the expectations they had; it's the culture that has been developed inside of 35th and Shields under executive vice president Ken Williams and GM Rick Hahn.

According to Jesse Rogers of ESPN, there is a culture of no accountability that has preceded new manager Pedro Grifol and even former manager Tony LaRussa. Through multiple sources, including new Yankees reliever Keynan Middleton, there were "no rules," coming into the White Sox organization.

"We came in with no rules," Middleton said to Rogers. "I don't know how you police the culture if there are no rules or guidelines to follow because everyone is doing their own thing. Like, how do you say anything about it because there are no rules?

"You have rookies sleeping in the bullpen during the game. You have guys missing meetings. You have guys missing PFPs (pitcher fielding practices), and there are no consequences for any of this stuff."

How, as a professional organization, can you allow your players not to be held accountable for missing things that are vital to what winning organizations do?

Rogers later went on to ESPN 1000 to talk with David Kaplan and Johnathan Hood and named specific players, including Yasmani Grandal, Yoan Moncada, and Eloy Jimenez, as guys who either aren't hard workers or are creating the current toxic culture. It was even reported that Grandal slapped Tim Anderson heading into the All-Star break because Grandal wanted to leave a day early, and Anderson said, "Fuck him. If he doesn't want to be here, I'll pay for his flight."

To call what is going on the South Side a mess is the understatement of the year.

I say this as a die-hard Cubs fan who wants the White Sox to succeed. Baseball in Chicago is always better when both teams are playing well. Everyone in the city wants that cross-town World Series between the North and South sides. The Mets and the Yankees had the "Subway Series" in 2000, and even the Athletics and Giants had their "Bay-Bridge Series" in 1989. Imagine (if these players stay) a World Series with the Cubs and Sox with Justin Steele and Dylan Cease going at it on the mound, Dansby Swanson vs Tim Anderson, and Cody Bellinger vs. Eloy Jimenez.

Well, as long as you're still the owner, that will never happen.

Now let's move to the court and look back at your time with the Chicago Bulls. The Bulls have had a similar trajectory to the White Sox. They have been entirely irrelevant basically since the Jordan years. I would argue that the Bulls would be the most irrelevant franchise in NBA history without Micheal Jordan. The family has done nothing since those titles and has coasted on those coattails ever since.

The Bulls have made the playoffs 12 times since 1999 but have only made it to the second round four times and only made it to the conference finals once in 2011 with Rose, where they lost in five games to the Miami Heat.

I don't blame you for what happened to Rose. That was just one of the most unfortunate injury-plagued careers in modern history, and nothing you could have done would have changed that. The time since then, however, that is all on you.

Your team has only made the playoffs twice since Rose was traded, where you lost in the first round both times, once to the Celtics in 2017 and then the Bucks in 2021. Your refusal to spend any big money has really hurt this team. Zach Lavine was the first player the Bulls gave a 100 million-dollar contract. I love Zach Lavine, but for him to be your most significant contract in franchise history is unacceptable.

Your refusal to go into the luxury tax for this team to get better makes the jobs for the front office that much harder. Every single team that made the conference finals except the Miami Heat has dipped into the luxury tax to get their team to make it there. The Heat themselves are only 1.1 million dollars away from the luxury tax line anyway.

You need to empower your front office to spend money in order to build a contending team.

You said this back in May at the Milken Institute Global Conference panel in Los Angeles:

You don't care about making money? Then why don't you spend some of the 2.2 billion dollars you're worth to do what you say you care about, winning? The thing fans want. They want you to spend money to get both these teams into winning windows.

But hey, like you said, you won't listen to us since you're worried about one day sitting with us.


Jackson Gross


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