The Worst Owner in Sports? The case for Jerry Reinsdorf

[Tony]

1 hour ago, FloydBannister1983 said:

Not necessarily bad signings just not evidence of Reinsdorf being a big spender to sign him to a relatively short term deal, which I believe is still the one of the largest contracts in team history.

 

Has Reinsdorf ever signed an 8 year contract with anybody?  I'm not aware of even any 6 year contracts.

No you are correct there. It was the most logical move given all the circumstances, but they've seemingly never won a true bidding war on a player that was in high demand. 

[WhiteSox2023]

2 hours ago, Tony said:

No you are correct there. It was the most logical move given all the circumstances, but they've seemingly never won a true bidding war on a player that was in high demand. 

I don’t know if it would have changed things as far as a WS, but just imagine one of Machado or Harper and Wheeler over Keuchel.  😢

[southsider2k5]

5 minutes ago, WhiteSox2023 said:

I don’t know if it would have changed things as far as a WS, but just imagine one of Machado or Harper and Wheeler over Keuchel.  😢

Wheeler doesn't bother me as badly as the Harper/Machado/TLR troika.

[Lip Man 1]

4 hours ago, 77 Hitmen said:

Whose decision was it to push Jeff Torborg out the door after the 1991 season?   Was that Reinsdorf or Schueler?  Another bone-headed move by this front office.   Was Gene Lamont any better?  Or how about Terry Bevington (lol)?

From my interview with Jeff Torborg:

ML: The Sox still won 87 games and looked ready to take the next step when word came that you resigned to take the Mets job. I remember reading that you wanted to be closer to your family in New Jersey, Jeff…but I’ve also heard rumors through the years that some in the front office didn’t care for the way you handled pitchers, specifically Bobby Thigpen who went downhill after 1991. When I’ve asked the guys you managed about that, like Donn Pall, he strongly defended the way you used the bullpen. Can you clear this up for me, why did you leave the White Sox? And were you forced out?

JT: “My mother was in her 80’s at the time but the reason that I left to be closer to my family was just for public relations, we didn’t want to hurt any feelings. I didn’t want to leave the White Sox. I had no desire to leave…why would I? This was a good young team ready to win; my wife and I loved Chicago and our son Dale was just starting out at Northwestern. (Author’s Note: Dale Torborg now works for the White Sox after a career in professional wrestling as a strength coach)

ML: Then obviously by your answer there’s more to the story than was told to fans at the time. What else was going on?

JT: “Later in the season we were in Minnesota for a two game series, it was a must win series for us because we were running out of time and I heard Peter Gammons report on ESPN that my job was in jeopardy. I was thinking, ‘where is this coming from?’ Then the last home stand of the year when we played the Twins again, Ron Schueler came into my office before it started and he closed the door. I was wondering what was going on. Ron said to me, “The Mets called me today and they want to talk with you about the managing job.” I told him, “Ron, I appreciate it but I have no interest.” Ron said, “well think about it and I’ll come back in a few days. We’ll talk again.” I’m sitting there wondering what is going on, because I said I had no interest.”

“So right before the last games, we had a makeup double header; Ron comes back and asks if I thought about the Mets offer. I told him again that I had no interest but then I said “Ron, I’ve got to ask you because this has come up, where I fit in with you and the organization?” He looked at me and said, “I think both of us would feel bad if you turned it down and then something happened.” 

“When he said that I had to think twice about what was happening. Ron and I never had a cross word between us that season but he wanted to hire his own guy, so when the Mets called I took the offer. It was the best thing for me financially but it was the worst move professionally I could have made. Ironically about a half hour after I verbally told the Mets I’d take the job the Yankees called and said they were firing “Stump” Merrill and offered me the position. I told them I had already given my word to the Mets and couldn’t go back on it but I didn’t want to leave the Sox in the first place.” (Author’s Note: Schueler and the organization first contacted former Sox coach Jimmy Leyland, then the manager of the Pirates about the position, but he turned them down instead suggesting his longtime base coach Gene Lamont, who got the job.)

ML: Was there any truth to the rumor that part of the reason the organization was upset with you was because of the way you handled your bullpen and how Bobby Thigpen just fell apart.

JT: “I had heard that I was being criticized by some of the guys upstairs on that. I mean Larry Monroe (Author’s Note: Advisor to the Baseball Department and former Sox pitcher), Ed Farmer, and Ron (Schueler.) They all wanted Scott Radinsky to be the closer. Now Scott was a good pitcher and he could be a closer but at that time he wasn’t ready.  The criticism was laughable; remember this was the bullpen that was the best in baseball in 1990.” (Author’s Note: The Sox won the Rolaids Relief Team Bullpen of the Year Award based on their record of 29-21 with 68 saves and an ERA of 3.16. The bullpen was primarily made up of right handers Bobby Thigpen, Barry Jones and Donn Pall and left handers Scott Radinsky, Kenny Patterson and Wayne Edwards.)

“As far as Bobby was concerned we played a game against the A’s in 1991. We had a lead and Bobby came in to pitch the 8^th inning for Alex Fernandez and a pitch got away from him and hit Terry Steinbach in the head. Tony (LaRussa) went crazy, I still remember him throwing a bat and my first thought was ‘what if that hit a fan? What kind of a lawsuit would he be looking at?’

“Anyway it was an ugly, ugly game, we lost the lead, wound up losing the game but there was a big fight after Steinbach got hit. Bobby was down on the bottom of the pile and he hurt his back. I think that’s why he lost his effectiveness not because of anything that I or the coaching staff did.” (Author’s Note: The game was played on June 1, 1991. The A’s came from behind to win 7-4.)

 

[Lip Man 1]

4 hours ago, FloydBannister1983 said:

Not necessarily bad signings just not evidence of Reinsdorf being a big spender to sign him to a relatively short term deal, which I believe is still the one of the largest contracts in team history.

 

Has Reinsdorf ever signed an 8 year contract with anybody?  I'm not aware of even any 6 year contracts.

I don't think he ever has done so. 

[NO!!MARY!!!]

On 10/26/2025 at 9:58 PM, Lip Man 1 said:

I think they have made the playoffs now five times in the past 10 years.

As a Sox fan I'd give a lot for that. 

I don’t buy that at all. They won only one World Series, then broke up that team by letting the two biggest stars leave via free agency and starting a rebuild. You would be happy with that? Come on. 

[southsider2k5]

15 hours ago, Tony said:

No you are correct there. It was the most logical move given all the circumstances, but they've seemingly never won a true bidding war on a player that was in high demand. 

1. Albert Belle.

That's it.  That's the list.

[Kyyle23]

1 hour ago, NO!!MARY!!! said:

I don’t buy that at all. They won only one World Series, then broke up that team by letting the two biggest stars leave via free agency and starting a rebuild. You would be happy with that? Come on. 

Those stars would have sunk them if they paid them what they were asking for.  Kris Bryant has played almost exactly a seasons worth of games for the Rockies in 4 years and until this season Baez has been an albatross contract for Detroit.  They absolutely made the right decision letting them walk.  And I would be pretty fucking happy if our rebuild lasted as long as theirs did and they went back to the playoffs already.  

[caulfield12]

1 hour ago, southsider2k5 said:

1. Albert Belle.

That's it.  That's the list.

Luis Robert Jr. vs. Cardinals

[Bob Sacamano]

16 minutes ago, caulfield12 said:

Luis Robert Jr. vs. Cardinals

Yeah back when the big spenders were in the "penalty box" from overspending the prior year (the old International Amateur rules).

[southsider2k5]

10 minutes ago, Bob Sacamano said:

Yeah back when the big spenders were in the "penalty box" from overspending the prior year (the old International Amateur rules).

Eh, it wasn't quite the same as ACTUAL free agent top of the market spending, but I will say it did set a record for that time period.

[Tnetennba]

19 hours ago, southsider2k5 said:

Wheeler doesn't bother me as badly as the Harper/Machado/TLR troika.

Wheeler has been great for the Phillies, and he would have been a force at the top of the rotation here, but 26 y/o generational talents don’t come around very often on contracts that would be bargains after a few years. Losing out on Wheeler didn’t set the organization back the way bungling Machado & Harper did. 

[Tnetennba]

6 hours ago, southsider2k5 said:

1. Albert Belle.

That's it.  That's the list.

Nearly 30 years ago. A baseball eternity. 

[southsider2k5]

6 minutes ago, Tnetennba said:

Wheeler has been great for the Phillies, and he would have been a force at the top of the rotation here, but 26 y/o generational talents don’t come around very often on contracts that would be bargains after a few years. Losing out on Wheeler didn’t set the organization back the way bungling Machado & Harper did. 

The team made an honest effort at Wheeler and set the market for him.  That's fine.

[77 Hitmen]

7 hours ago, southsider2k5 said:

1. Albert Belle.

That's it.  That's the list.

 

1 hour ago, Tnetennba said:

Nearly 30 years ago. A baseball eternity. 

It was also in all likelihood a "middle finger to the rest of the owners" free agent signing because JR was unhappy with what they settled for to end the strike.  

Also note that the Sox included a perfect opt-out clause that would allow Belle to declare free agency after only 2 seasons here.   In the end, the Sox only paid Belle $20M total, not the $55M he was signed for.  

[Lip Man 1]

4 minutes ago, 77 Hitmen said:

 

It was also in all likelihood a "middle finger to the rest of the owners" free agent signing because JR was unhappy with what they settled for to end the strike.  

Also note that the Sox included a perfect opt-out clause that would allow Belle to declare free agency after only 2 seasons here.   In the end, the Sox only paid Belle $20M total, not the $55M he was signed for.  

The clause that triggered his "out" was that he had to be among the top three players in the game. 

[77 Hitmen]

On 10/30/2025 at 9:33 AM, FloydBannister1983 said:

Spending money on short term contracts that get you out from under them quickly is not really spending money.  It’s smoke and mirrors.  A parlor trick and unhealthy candy for the fans.  A Harper signing would have been a healthy signing.  A Grandal and Benitendi and Belle signing are silliness.

This is the way Jerry has run the Sox for at least the last 20 years now - a lot of smoke and mirrors and never seriously investing in scouting/player development and/or landing marquee free agents.  

[caulfield12]

1 hour ago, 77 Hitmen said:

This is the way Jerry has run the Sox for at least the last 20 years now - a lot of smoke and mirrors and never seriously investing in scouting/player development and/or landing marquee free agents.  

Unless one considers Dunn Robertson Kimbrel and Grandal to be top of the line...Dunn was pretty darned close in 2011.

[Texsox]

There isn't an owner responsible for wins, that credit goes to the players. But loses fall in their laps. That's just the nature of the world. In that regard that makes JR about the worst of the worst. Start factoring in things like market size and he looks even worst. 

Other owners only take action when an owner is accused of harassment or racist comments. If some franchise wants to be the Washington Generals the other owners don't care. So there really aren't many bad owners in their eyes. 

Sports are a weird business. I want someone to make a fortune in another business then spend all that further to make my team a winner. 

[caulfield12]

6 minutes ago, Texsox said:

There isn't an owner responsible for wins, that credit goes to the players. But loses fall in their laps. That's just the nature of the world. In that regard that makes JR about the worst of the worst. Start factoring in things like market size and he looks even worst. 

Other owners only take action when an owner is accused of harassment or racist comments. If some franchise wants to be the Washington Generals the other owners don't care. So there really aren't many bad owners in their eyes. 

Sports are a weird business. I want someone to make a fortune in another business then spend all that further to make my team a winner. 

Or run your team like TB Cleve Milwaukee...at least figure out a way to be competitive with a lower payroll.

[Texsox]

48 minutes ago, caulfield12 said:

Or run your team like TB Cleve Milwaukee...at least figure out a way to be competitive with a lower payroll.

Actually, don't run anything. Hire good people and support them. Give them a reasonable amount of time and if their plan doesn't work move on. 

[kitekrazy]

1 hour ago, caulfield12 said:

Or run your team like TB Cleve Milwaukee...at least figure out a way to be competitive with a lower payroll.

that really doesn't do it anymore.......being a token playoff team

[77 Hitmen]

5 hours ago, caulfield12 said:

Unless one considers Dunn Robertson Kimbrel and Grandal to be top of the line...Dunn was pretty darned close in 2011.

The White Sox never signed Kimbrel.  They acquired him for Nick Madrigal and he only played for us for 2 months appearing in 24 games for the South Siders.

Dunn might be the closest to a top free agent that the Sox have signed, but he was nowhere near the same quality player as Tori Hunter, Manny Machado, or Bryce Harper.  I can think of a lot of free agents over the years who were bigger difference makers than Adam Dunn.  

I wouldn't exactly call Grandal a marquee free agent.  Maybe in White Sox World, a 4-year/$73M contract to a 31-year old catcher is considered an exorbitant, franchise centerpiece contract since he was the team's biggest contract ever at the time.  Everyone else except the A's have handed out contracts over $100M.  It was a good signing at the time, but I wouldn't exactly consider Grandal a franchise player. 

Robertson - again in White Sox World, that's a monster contract - $46M.  A very good relief pitcher and great acquistion, yes.  But a one-time all-star.  For teams who are actually serious about winning signing someone like Robertson would just be one important piece to the puzzle.  But for us, he's the one of the few shining examples of how Uncle Jerry really does spend on free agents.   

[caulfield12]

54 minutes ago, 77 Hitmen said:

The White Sox never signed Kimbrel.  They acquired him for Nick Madrigal and he only played for us for 2 months appearing in 24 games for the South Siders.

Dunn might be the closest to a top free agent that the Sox have signed, but he was nowhere near the same quality player as Tori Hunter, Manny Machado, or Bryce Harper.  I can think of a lot of free agents over the years who were bigger difference makers than Adam Dunn.  

I wouldn't exactly call Grandal a marquee free agent.  Maybe in White Sox World, a 4-year/$73M contract to a 31-year old catcher is considered an exorbitant, franchise centerpiece contract since he was the team's biggest contract ever at the time.  Everyone else except the A's have handed out contracts over $100M.  It was a good signing at the time, but I wouldn't exactly consider Grandal a franchise player. 

Robertson - again in White Sox World, that's a monster contract - $46M.  A very good relief pitcher and great acquistion, yes.  But a one-time all-star.  For teams who are actually serious about winning signing someone like Robertson would just be one important piece to the puzzle.  But for us, he's the one of the few shining examples of how Uncle Jerry really does spend on free agents.   

Oops meant Liam Hendriks.

Was one tier above Robertson, arguably.

Edited November 1 by caulfield12

[Texsox]

Signing marquee free agents or locking your players into high dollar, multi year contracts, is certainly a criteria for being a good owner. However I think average total payroll is better, especially in baseball.