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Maybe it’s time for these owners to sell their teams?

Thursday, Sep 25, 2025 - Posted by Rich Miller

* Ridiculous…

Please sell the team, Jerry.

The Sox are not close to the in-a-row-record yet, but they are one more 100+ loss season away from the four in a row by the New York Mets expansion team.

* On the other end of the financial spectrum

The NFL’s finance committee approved the sale of 2.35% of the Chicago Bears to existing owners of the team in a deal that sets a league record and values the Bears at $8.9 billion, according to three people familiar with the matter.

The deal closed several days ago, according to one of the people.

The stake was held by the estate of Andrew McKenna, according to two people familiar with the deal. McKenna died in 2023.

The Bears were valued at $6.4 billion just a year ago in CNBC’s Official NFL Team Valuations — No. 10 among the league’s 32 teams.

Time to cash in, McCaskey fam.

Your thoughts?

       

29 Comments »
  1. - Chambanalyst - Thursday, Sep 25, 25 @ 10:59 am:

    Long overdue. White Sox are legitimately fading into irrelevancy, and I couldn’t agree more with the McCaskey’s cashing in. Out with the old, in with the new. City deserves better.


  2. - Candy Dogood - Thursday, Sep 25, 25 @ 11:01 am:

    ===Your thoughts? ===

    What’s the point of wealth if you can’t also consistently disappoint millions of people and constantly troll them with confusing and questionable decisions?

    A McCaskey family without the Bears is just a bunch of rich white people of no note nor significance.

    Even a billionaire can still feel insignificant. The only difference is that they can surround their insecurities with people who will tell them they’re the greatest people who have ever lived.

    Some folks become rich so that they can have the opportunity to poorly run a sports franchise. The McCaskeys were born into it. Hard to give that up.


  3. - low level - Thursday, Sep 25, 25 @ 11:06 am:

    ==What’s the point of wealth if you can’t also consistently disappoint millions of people and constantly troll them with confusing and questionable decisions?==

    Precisely. If the McCaskey’s sold the Bears, they would just find another industry to get involved in and screw up. I gave
    up on the Bears after the double doink missed field goal in 2019.

    As for the White Sox, I have been to only one game the past 8 yers despite being a lifelong fan.


  4. - fs - Thursday, Sep 25, 25 @ 11:06 am:

    If the McCaskey’s aren’t selling after Virginia died, I don’t see them doing so in the foreseeable future. However, if they’re wanting to upgrade their home, they could sell a small portion of it to help pay for it. Like most people who take out a home equity loan to improve their property, and can’t rely their government to pay for it.


  5. - Been There - Thursday, Sep 25, 25 @ 11:07 am:

    The McCaskey’s should sell at least 51% of the team. That is over $4.5 billion for the family to split up. And then they can be just like Andy McKenna was as a minority owner. Andy didn’t get to benefit from that $200 mil that the estate got from the Bears. But his heirs did and I am pretty sure the McKenna’s got some pretty good seats to every game (probably still had to pay for them but so do the rest of us).


  6. - heyhey - Thursday, Sep 25, 25 @ 11:07 am:

    My understanding is Jerry sold majority of Sox to Ishbia, the deal is just structured to where it will take a number of years before Ishbia is the majority owner.


  7. - DuPage Saint - Thursday, Sep 25, 25 @ 11:13 am:

    That value of the Bears is without a stadium and without all the parking and concessions. What will they be worth when they own their own stadium? They don’t need tax certainty


  8. - Tammy - Thursday, Sep 25, 25 @ 11:16 am:

    One can make a pretty good argument that these White Sox stand with the early 1960’s Mets as the two worst teams in baseball history. Not only did the Sox set a record with 121 losses last year, but very few MLB franchises have lost 100 games three seasons in a row. At least the Mets had the excuse of being an expansion team.

    A change in ownership for the Sox and Bears might increase the chances of both getting the new stadiums they want.


  9. - H-W - Thursday, Sep 25, 25 @ 11:18 am:

    There is a concept called social responsibility. It should apply here, since these teams have names that suggest they are somehow related to Chicago. Chicago is a city of several million people.

    The socially responsible thing to do would be to find ways to win, rather than continually embarrass the citizenry who shares that name.

    Sell. Sell now. Sell often. Both teams.


  10. - Former State Worker - Thursday, Sep 25, 25 @ 11:19 am:

    Jerry is already selling the team to Ishbia.


  11. - Saluki24 - Thursday, Sep 25, 25 @ 11:21 am:

    In a word: absolutely.

    Regarding the White Sox, baseball’s next labor agreement will be fascinating. The current structure (no salary floor, revenue sharing) enables terrible teams to still turn profits (see: Pirates, etc.). There are too many MLB owners who view teams as business investments to simply make money, regardless of how the team does on the field. That structure needs to change.

    Regarding the Bears: after all the front office and coaching changes that are akin to shuffling the chairs on the Titanic, what else is left but to change ownership?


  12. - lake county democrat - Thursday, Sep 25, 25 @ 11:29 am:

    Forgive a pollyanish moment, but are the Sox in that bad shape? The rebuild has a promising core, with some decent prospects in the minors and a good chance to land the #1 pick in next year’s draft. They’ll soon be shedding Benintendi’s contract and the deal they made with Ishibia hints that he might be providing some money prior to his buying majority ownership.


  13. - Rich Miller - Thursday, Sep 25, 25 @ 11:41 am:

    ===Jerry is already selling the team===

    I’ll believe that when I see it.


  14. - Rahm's Parking Meter - Thursday, Sep 25, 25 @ 11:42 am:

    Sell the TEAMS.


  15. - walker - Thursday, Sep 25, 25 @ 11:45 am:

    @lake country democrat Hat tip to you

    Ya gotta love a true fan.


  16. - Harrison - Thursday, Sep 25, 25 @ 11:48 am:

    It’s official but unfortunately for Candy Justin Ishbia is also a white billionaire

    https://www.mlb.com/amp/news/white-sox-announce-long-term-ownership-investment-agreement.html


  17. - Stones - Thursday, Sep 25, 25 @ 11:57 am:

    I’ve met Jerry Reinsdorf. He’s a nice guy and I believe he was truly interested in a winning baseball team 20 years ago. Somewhere along the line he lost interest and focus. IMHO part of the problem is blind loyalty to people that have worked for him over the years and haven’t kept up with the times. This sale can’t go through fast enough. As to the Bears, I don’t believe the McCaskey family will sell during my lifetime.


  18. - Frida's Boss - Thursday, Sep 25, 25 @ 11:57 am:

    I believe the White Sox are already on the auction block to the Ishiba’s and will go through.

    The Ryan family owns 23% of the team currently and has first rights to purchase the team.

    Is it more profitable to sell the team now or after the stadium and surrounding area is built. Then sell the team and lease the stadium to new owners and keep the surrounding area? Or will any new owner want all of it? And if they do, will they want to build their own stadium or let the McCaskey’s decide what the stadium should look like?


  19. - JS Mill - Thursday, Sep 25, 25 @ 12:10 pm:

    =is also a white billionaire=

    Is that a problem for you? Candy never mentioned his ethnicity.


  20. - Tax Attorney - Thursday, Sep 25, 25 @ 12:15 pm:

    https://www.southsidesox.com/2022/8/29/23325369/jerry-reinsdorf-selling-chicago-white-sox-not-on-his-life

    The timing of any sale will depend on whether the Reinsdorf family prefers to pay the estate tax or capital gains tax.


  21. - Pundent - Thursday, Sep 25, 25 @ 12:43 pm:

    =It’s official but unfortunately for Candy Justin Ishbia is also a white billionaire=

    From the article you cited:

    “There is no assurance that any such future transaction will occur, and in no event will such a transaction take place before 2029.”

    So it’s going to be awhile. And it still may not happen.


  22. - Rich Miller - Thursday, Sep 25, 25 @ 12:50 pm:

    ===And it still may not happen===

    Exactly.


  23. - Harrison - Thursday, Sep 25, 25 @ 1:02 pm:

    Did you read her comment?

    She mentioned the McCaskey family ethnicity and wealth as problematic for some reason

    Virginia Mc Caskey lived very modestly for most of her life in Mount Prospect

    With the exception of the Packers who are owned by over 500,000 fans all other NFL teams are owned by billionaires

    As far as minority ownership a record number of minorities now are part owners of NFL teams


  24. - fs - Thursday, Sep 25, 25 @ 1:34 pm:

    == With the exception of the Packers who are owned by over 500,000==

    The only thing those 500,000 people own is a piece of paper to hang on their wall, in exchange for participating in a fundraiser for a multi-billion dollar “non-profit organization”


  25. - Homebody - Thursday, Sep 25, 25 @ 1:44 pm:

    The more I’ve aged, the more I realize most professional sports teams are functionally emotional terrorists. They want to hold a fanbase hostage through nostalgia and unearned good will to extract ransoms in the form of inflated ticket and concessions prices and slurping off the public trough.

    I’m not quite at the point of actively campaigning against anything a for profit entertainment company does, as I am totally in support of development of mixed use entertainment and commercial districts, broadly speaking. But I am getting more and more militant against any invocations of “community spirit” or whatever nonsense the multi-billion dollar entertainment companies try to peddle to con local and state governments out of subsidies.


  26. - Candy Dogood - Thursday, Sep 25, 25 @ 2:34 pm:

    ===Did you read her comment?===

    Did you read my comment? I used it as a descriptor to emphasis how incredibly generic the McCaskey family is if they aren’t the owners of the Bears.

    Weird thing for you to latch on to and I will not be apologizing for your white fragility.


  27. - ChicagoBars - Thursday, Sep 25, 25 @ 2:45 pm:

    “== With the exception of the Packers who are owned by over 500,000==

    The only thing those 500,000 people own is a piece of paper to hang on their wall, in exchange for participating in a fundraiser for a multi-billion dollar “non-profit organization” ”

    Like 500,000 Bears fans wouldn’t take that Packers deal in a second over current Bears management if NFL rules still allowed that form of ownership (they do not).


  28. - Harrison - Thursday, Sep 25, 25 @ 2:50 pm:

    Like them or not the family is not generic for anyone with an understanding of the history of the NFL.

    Their family patriarch “Papa Bear” was one of the co founders of the AFL which became the NFL in 1922.

    In addition to founding the Bears in 1921 he was one of the first 17 inductees to the NFL Hall of Fame.

    The NFC Championship trophy is named the Halas trophy for good reason.


  29. - Juice - Thursday, Sep 25, 25 @ 3:01 pm:

    Harrison, you’re talking about George, and not his relatives who have run the team for the last 42 years.

    Which was essentially Candy’s point.


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