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The Worst Owner in Sports? The case for Jerry Reinsdorf

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Toronto finished in last place last year.

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  • The White Sox and baseball in general were probably THE stabilizing force in my life since I was a child, the one consistent activity I had was watching and talking about white Sox baseball, hence why

  • Bob Sacamano
    Bob Sacamano

    Wait, you’re trying to use the Bears as an argument for why the Sox don’t suck or something?

  • He has left a lot of money on the table and depreciated the value of his organization by being such a penny pinching dipshit 

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7 hours ago, 77 Hitmen said:

 

Jerry has been running a 2nd-rate operation with the Sox for years.   They were perfectly situated to sign either Machado or Harper, but that was never going to happen with JR as owner.  Only one of two franchise that has never signed a player to a $100M contract with the other franchise being literally homeless now. 

Passing up on Hinch in favor of brining TLR surely earns him lots of points towards the "worst owner in sports" award.  

In a couple years they will sign a $100 million contract and use it as evidence they’re not what we said they were, all while everyone else in the league has signed $200 million contracts.  They will always be 10+ years behind.

2 hours ago, Falstaff said:

Toronto finished in last place last year.

#1 they were in the best division in baseball in the AL East.

#2, they were still 33 games better than the White Sox in 2024.

#3, their 2024 was still 14 games better than the White Sox in 2025.

4 hours ago, Falstaff said:

Toronto finished in last place last year.

....and even with that down year, they're still averaging 88 wins per season over the last 5 years in a very tough division.  

12 hours ago, WestEddy said:

Run into many at the Scottsdale Starbucks?

that should be enough to shatter your wet dream

On 10/20/2025 at 12:03 PM, Kalapse said:

The White Sox and baseball in general were probably THE stabilizing force in my life since I was a child, the one consistent activity I had was watching and talking about white Sox baseball, hence why I joined this site 21 years ago and became a regular. After 35 years of constant disappointment with zero hope in sight I decided to relinquish my fandom and cut the team out of my life. Instead on being jaded and synical, constantly bitching about Sox minutea that will not improve anytime soon I decided to just stop following them one day and you know what? I'm a lot better off for having done so, I'm infinitly happier in my life doing things that I enjoy. My removing the one thing from my life that I held most dear was 100% in response to JR's dreadful fucking ownership, I have zero positive feelings towards that man and the way he chooses to run his sports franchises. Its just further proof that you can find tremendous success in the business world and still be an enormous fucking loser. 

This summer, mostly because of the TV deal, I rarely watched a game. 

Once it was on tv, I still rarely watched a game. I had no idea who made the playoffs. I barely paid attention. If it wasn't because of this community, which I have been a part of for 20 years, Idk if I would have paid attention at all. 

I used to say that Baseball is your friend. No matter how much it pisses you off one day, it's there tomorrow to start anew. 

After years of being pissed, I have had enough. 

I have no intention of watching next year. I have already cut out the Bulls. Wake me up when there is new ownership and a deal to remain in Chicago.

6 hours ago, southsider2k5 said:

#1 they were in the best division in baseball in the AL East.

#2, they were still 33 games better than the White Sox in 2024.

#3, their 2024 was still 14 games better than the White Sox in 2025.

So you're saying we have a chance.😀

Edited by Falstaff

On 10/20/2025 at 2:41 AM, NO!!MARY!!! said:

“Reportedly.”

 

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I don’t think he’s always been the worst owner. He was at least average for years. But he is horrible now for sure with both teams. Probably is as bad as there is.

9 minutes ago, Dick Allen said:

I don’t think he’s always been the worst owner. He was at least average for years. But he is horrible now for sure with both teams. Probably is as bad as there is.

It's weird, but a part of me wonders if 2005 was the worst thing to happen to this franchise long term.  Yes we got a title, but it also seems to convince Jerry that he knew what he was doing better than pretty much anyone else except maybe Tony.  The last two decades have been a worst case scenario, and Jerry has become more and more convinced he just needs yesmen instead of anyone who might challenge him.

27 minutes ago, southsider2k5 said:

It's weird, but a part of me wonders if 2005 was the worst thing to happen to this franchise long term.  Yes we got a title, but it also seems to convince Jerry that he knew what he was doing better than pretty much anyone else except maybe Tony.  The last two decades have been a worst case scenario, and Jerry has become more and more convinced he just needs yesmen instead of anyone who might challenge him.

There's a lot of truth in this post, I've thought the same thing myself. Winning the title convinced JR his way was the right way and there was no need to change things. Very glad the Sox finally won the series but the ramifications of winning it may have shaped how things were going to be done moving forward.  

11 hours ago, southsider2k5 said:

It's weird, but a part of me wonders if 2005 was the worst thing to happen to this franchise long term.  Yes we got a title, but it also seems to convince Jerry that he knew what he was doing better than pretty much anyone else except maybe Tony.  The last two decades have been a worst case scenario, and Jerry has become more and more convinced he just needs yesmen instead of anyone who might challenge him.

I'm sure what you write is accurate. To him the WS only showed him how he knew more than anyone else. If you remember, he and Krause couldn't wait for the Jordan era to end so they could show it wasn't MJ, it was them. And his baseball is still the same. He's had one way to do things, and what worked in the 80s doesn't work anymore, at least long term. So we are just stuck waiting for his reign of terror to end. 

1 hour ago, Dick Allen said:

I'm sure what you write is accurate. To him the WS only showed him how he knew more than anyone else. If you remember, he and Krause couldn't wait for the Jordan era to end so they could show it wasn't MJ, it was them. And his baseball is still the same. He's had one way to do things, and what worked in the 80s doesn't work anymore, at least long term. So we are just stuck waiting for his reign of terror to end. 

Good call back on the Bulls/MJ/Krause stuff.  Too bad he didn't learn his lesson then.

I think Moreno might be worse.  Wasting Trout and Ohtani is criminal.  

Edited by Colome's Hat

  • Author
18 minutes ago, Colome's Hat said:

I think Moreno might be worse.  Wasting Trout and Ohtani is criminal.  

Reinsdorf wasted plenty of primes himself.  Ventura and Thomas in the 90s should have been in a lot of playoffs.   He chased off Jordan after the second three peat.  He refused to allow the front office to super team with LeBron around Derrick in that small window that he was healthy 

moreno sucks in one sport, Jerry sucks in two

3 minutes ago, Kyyle23 said:

Reinsdorf wasted plenty of primes himself.  Ventura and Thomas in the 90s should have been in a lot of playoffs.   He chased off Jordan after the second three peat.  He refused to allow the front office to super team with LeBron around Derrick in that small window that he was healthy 

moreno sucks in one sport, Jerry sucks in two

I think the White Sox have been more competitive and successful with Reinsdorf then the Angels with Moreno.  A broken clock can be right occasionally.  

  • Author
3 minutes ago, Colome's Hat said:

I think the White Sox have been more competitive and successful with Reinsdorf than the Angels with Moreno.  A broken clock can be right occasionally.  

lol, no 

 

 

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  • Author

You forget that the angels were pretty damn good at the front end of Arte’s ownership 

  • Author

jordan era -> full reinsdorf era

 

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They also didn't win a world series.  If we are taking to account full ownership, Reinsdorf has seven championships and Moreno has zero.  I don't like Reinsdorf.  I just don't think he's the worst.

Also, if you are talking sports, this includes the global world, there are many european football owners who are FAR worse then Reinsdorf.  We are talking letting their teams go bankrupt and lose professional standing.  All you have to do is go to the EFL.  I'm sorry but I do think this needs to be pointed out to be put into context.  I legitimately think Spurs ownership is worse then Reinsdorf, although Levy is actually a good comp to him. 

1 hour ago, Colome's Hat said:

They also didn't win a world series.  If we are taking to account full ownership, Reinsdorf has seven championships and Moreno has zero.  I don't like Reinsdorf.  I just don't think he's the worst.

The Angels have consistently run a Top 10 payroll and at least attempted to compete with the cross town Dodgers instead other totally surrendering the market like JR.

They also brought two Hall of Famers in Trout and Ohtani into the game.

More like the Phoenix Suns under Ishbia.

And more often that not they have tried to run competitive teams out there.

Even this year's squad was .500ish for most of the year.

1 hour ago, Colome's Hat said:

They also didn't win a world series.  If we are taking to account full ownership, Reinsdorf has seven championships and Moreno has zero.  I don't like Reinsdorf.  I just don't think he's the worst.

Moreno at least has been trying to win his entire tenure. Trying to win is much more valuable than what Jerry has been doing imo.

That said, obviously John Fisher is worse than Jerry. He doesn't spend any money or try to win, he actively forces stars out of town, he tanked the team and stadium in Oakland so he could move the team to Vegas who doesn't even want a team, and he's now playing in Sacramento in a minor league sham of a stadium. He basically ran a public hate-campaign against Oakland and their fans. At least Jerry has the respect to hate us mostly in private.

Jerry has had periods where he invested to win. 

While the A's have had some nice seasons, it's been in spite of Fisher. 

2 hours ago, Colome's Hat said:

I think Moreno might be worse.  Wasting Trout and Ohtani is criminal.  

Moreno is at least willing to spend.  Trout would have been a free agent without the large extension if he was a White Sox.  Ohtani left to chase wins more than he did money.

11 minutes ago, Look at Ray Ray Run said:

Moreno at least has been trying to win his entire tenure. Trying to win is much more valuable than what Jerry has been doing imo.

That said, obviously John Fisher is worse than Jerry. He doesn't spend any money or try to win, he actively forces stars out of town, he tanked the team and stadium in Oakland so he could move the team to Vegas who doesn't even want a team, and he's now playing in Sacramento in a minor league sham of a stadium. He basically ran a public hate-campaign against Oakland and their fans. At least Jerry has the respect to hate us mostly in private.

Jerry has had periods where he invested to win. 

While the A's have had some nice seasons, it's been in spite of Fisher. 

Yeah, I can't even argue this one.

 

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