The Phillies playing the Pirates last weekend got me thinking about how unfortunate it is that Paul Skenes landed with such a disaster of an organization. Even though it is only his second year, all of baseball is counting down the days until one of the best pitchers in baseball is inevitably traded. There is simply no world in which they extend him and they don’t seem interested in building a team around him. That got me thinking, is Bob Nutting the worst owner in baseball?

Sure, there are teams that could be run better, but to make this final cut for this truly awful collection of shitheads, you have to really earn it. What I am looking for isn’t just the dumb owners or the cheap owners or even the owners who seem to openly hate their fans, but the truly despicable owners that check all 3 boxes. You can be cheap or you can be dumb, but being both and not caring about your fans? Why even own the team?

5. Rockies – Richard and Charles Monfort: These two seem about as good at running a baseball team as the Maloof brothers running the Kings. They famously ran the Kings into the ground and almost had it moved to Seattle. Like the Maloofs, the Monforts are nepo babies whose father sold the family meatpacking business to Conagra and they then received cushy jobs in the aftermath. Despite not having the deepest pockets they do at least manage to consistently run a middle of the pack payroll. The problem isn’t love of the team; it is that they genuinely have no idea what they are doing. Year after year they sign bad contracts, make bad trades, draft poorly, and never develop anyone. The team has 5 winning seasons in 32 years and are currently on pace for the single worst season in major league history.

That’s the kicker here and why they are on the list and not Angels owner Art Moreno. In 32 years of being with the club, its entire history, they still have not figured out how to do anything right. Playing at Coors Field has a unique set of problems, but the brothers have yet to invest in any way to gain an advantage from this. The Yankees and Red Sox play in bandboxes and employ hitters to take advantage of this. The Rockies do not.

The city of Denver apparently LOVES the team. They may be regularly awful, but they still draw in about 75% capacity every night for 30 years. The Monfort family as owners do the city of Denver a disservice by continuing to run the team. These fans deserve a better class of ownership, one they have literally never had. Maybe this current 28 win pace will finally change things? Not likely.

4. Marlins – Bruce Sherman: The Marlins are no strangers to bad ownership. The previous regime was terrible, pulling off a quintet of Miami cardinal sins of being cheap, boring, and ugly, while literally stealing from the city, and destroying the pride and joy of Little Havana, the Orange Bowl. The Marlins thought they were getting something completely different when Bruce Sherman took charge with Derek Jeter. Sorry Miami, it might be even worse.

The final parting shot previous owner Jeffrey Loria took at the city was selling the Marlins for too much money. New ownership not only barely had enough cash for the transaction, but the team was immediately underwater in value. What started with hope of team spending was put immediately back in the red. In order to pay for itself, the team has to make a profit or else it can’t go on running. So, payroll was slashed and players were traded. Same old, same old for the Marlins.

Do you know how hard it is for baseball to fail in a city like Miami? The city LOVES baseball. The Capital of Latin America should be Yankees South in terms of attracting interest as it is a melting pot of baseball lovers. Youth baseball is played all year round here too. Business should be booming. I guess the real question is why did MLB approve the sale of a team to an ownership group without money? This could have been avoided. Before Sherman purchased the team, it was reported that the winning bid was by a guy named Jorge Mas, owner of construction giant MasTec, who is worth around $2.5b. When Loria went with Sherman instead, Mas and his family pivoted to Inter Miami. They then lured Lionel Messi to America and turned that team into a champion and $1b franchise. You think the Marlins could have used some of that juice?

On a personal side, I have a son who loves the Marlins. We live here. Try as I might, he isn’t interested in being a Philly fan. I respect that (even if I hate it). Still, his favorite player is Jazz Chisholm…at least it was. For two years I was just waiting for the Marlins to trade him. What was I going to tell my kid? I know players get traded, but this was just as inevitable as it was unnecessary. It’s simply because the Marlins are cheap. That’s it. How do you explain that to a kid? I tried to hype up the prospects, but that doesn’t work for an 8 year old. He doesn’t have a favorite Marlin right now. How could he? I did take that opportunity to get him a Kyle Schwarber jersey though. I’m not giving up. (Don’t worry, my other kid proudly reps Jalen Hurts and Bryce Harper jerseys)

3. Pirates – Bob Nutting: What is the point of him? The Pirates are a beloved franchise, with a fantastic ballpark, and a billionaire owner. Unfortunately, that owner seems to hate the team. “Bottom Line Bob” routinely has the Pirates ranked at the bottom of the standings and in payroll. In his 18 years in charge, outside of Andrew McCutchen lead playoff teams in 2013-15, the Pirates have not made the playoffs. He has stewarded a franchise that was about 300 games over .500 in over 100 years of history to now well below and dropping. They did trade away Mr. Pirate McCutchen though as well as ace Garrett Cole. Throw in one of the worst trades ever in acquiring Chris Archer for Austen Meadows, Tyler Glasnow, and Shane Baz and you have a real winner under his stewardship.

The problem with Nutting is the depression he has brought to a famous franchise. Granted he hasn’t threatened to move or do anything outwardly evil, but he has taken away all hope and joy from a once proud fanbase. The Pirates have no chance. Despite having a pretty solid pitching staff led by maybe the best pitcher in the world, they know, and we know that the team is going to lose. There isn’t ever enough talent, and the Pirates do nothing but shop for bargains to fill out the roster. This is especially bad when you find out that Mark Cuban has been a waiting and willing buyer of the franchise for 20 years. Nutting simply has no interest in selling.

He has no interest in appearing either. One of the major knocks on Nutting as an Owner is that he is reclusive, refusing to take any real questions about the team or responsibility for the team’s lack of competitiveness. He famously claimed to be coming to Pirates fanfest to answer fan questions, then didn’t show up when he was expected to be hit with a barrage of “sell the team” pleas. He gets the nod over Sherman only because he’s been there 10 years longer and we expect him to screw up Paul Skenes. Both the Marlins and Pirates are almost completely irrelevant.

2. Not Oakland Athletics – John Fisher: Surprisingly, I started with Fisher not on the list. Then I moved him to 5th. As I read more and more about the situation in Oakland though, his nefarious deeds became impossible to downplay. He is the Thanos of a list like this, inevitable. Right off the bat you see that his team is somehow worse off than the Angels in that instead of having two city names, the A’s have none at the moment: opting instead for simply “A’s” instead of acknowledging their 3-year temporary home of Sacramento. How did they get to this point?

He didn’t start as the supervillain of owners. The A’s made the postseason 7 times in his first 14 seasons in charge despite an incredibly low budget. Granted, this low budget was self-imposed considering his $2b fortune but at least there was a plan in place to compete. Then the greed set in. Fisher had grand plans of developing the A’s into a multipurpose cash cow as he showed off his $12b district construction plan with the A’s at the center. He’d pay for the stadium if the city paid for everything else. Well Oakland wasn’t down with that. To get his way, he started truly tanking the team under the guise of lack of stadium revenue. The low payroll was cut back even more and ticket prices were doubled. He didn’t want people showing up, and they didn’t. That was only part of it.

One main problem with getting an alternative new stadium built in Oakland was that he steadfastly refused to improve the current stadium or let anyone build anywhere near it. The Raiders blame Fisher completely for their flight from the city saying that as tenants, they were not allowed to improve the stadium or build anything on the property. Efforts of a joint stadium project were rejected. Fisher wanted the stadium to fall into disrepair and it did. Aside from the sewage problem destroying the clubhouse, there are apparently dueling packs of native cats and opossums living and thriving within the stadium confines. I’ve been there. The whole area looked abandoned years before it officially was. Not since the days of Rachel Phelps has an owner so openly despised the players and fans in such a naked attempt to move the franchise. Except it didn’t work in movie Cleveland and it did in real life Oakland.

1. White Sox – Jerry Reinsdorf: Reinsdorf bought the team from legend Bill Veeck in 1981. Despite an initial influx of cash into the team, he is known as maybe the cheapest owner in sports. This isn’t just limited to baseball either as he famously feuded about money with Michael Jordan, Scottie Pippen, and Phil Jackson at the peak of the Bulls powers in the 90s, eventually leading the team to disband. Still, he agreed to pay MJ $30m and $33m per season for his final 2 years with the Bulls in 97 and 98. Why is this notable? It is more than he has ever paid any White Sox player in a season by about 70% and that was in 1998. The largest per year amount he ever gave out to a baseball player is the $18.5m to Dallas Keuchel before the 2020 season (this off season will be its own article). The largest White Sox contract period is Andrew Benintendi’s 5/$75m deal. He had given Albert Belle 5/$55m almost 30 years ago and has barely moved up from that since. That’s crazy. He is one of the cheapest of the cheap despite being worth $2b and purchasing both of these teams for almost nothing in today’s money. They are worth a combined $8b now.

If you look at his team payroll by year, it is kind of erratic. Some years he spends, some years he doesn’t. This is because he isn’t just cheap, he is miserly. When he is convinced to spend money and it doesn’t work out, he takes it personally and then withholds future funds. After the pre-2020 spending spree followed by Covid, he shut the wallet up tightly.

Probably most frustrating to White Sox fans though is that Reinsdorf doesn’t see the value of investing in the team at all. It is easy to blame a player when he doesn’t pan out, but what happens when the whole team doesn’t pan out repeatedly? What has happened to the White Sox over the last few years goes beyond bad luck, it is institutional malpractice. Eloy Jimenez, Luis Robert, Yoan Moncada, Tim Anderson, Andrew Vaughn, Oscar Colas, and Nick Madrigal all flamed out so badly that it ruined an entire generation of White Sox history. Whether it is lack of player development programs or the same bad attitude that blew up the Bulls great era, something is always rotten on the South Side.

Even their few success stories like Chris Sale, Garrett Crochet, and Dylan Cease all wanted out knowing Chicago was a dead end. The players know this because, well aside from history, Reinsdorf is regularly behind league labor strife, personally railing at the players’ and their representation. He is ALWAYS on the hardline against player salaries and has been one of the final holdouts in every work stoppage MLB has seen in the last 45 years. In two years, when the owners lockout the players again, you can bet Reinsdorf will be at the heart of the problem.

Cheap and bad, ok, but still not worse than Fisher right? He hasn’t moved the team from Chicago. Yeah? Well, he’s tried before, and he is currently doing it again. Back in the 80’s, he legitimately threatened to move the team to St. Petersburg if he didn’t get a new ballpark. The city and the state stepped in and made him a new park that he did not have to pay for. Now here we are 30 years later and he is threatening to move the team to Nashville unless he gets a new stadium district that seems very similar to what the Athletics were looking for out of Oakland. Except in this one, Reinsdorf wants the city to pay for the stadium and for him and friends to own the surrounding district.

Is he as evil as Fisher? No. Still, I give Reinsdorf the title because he was pulling Fisher’s crap for 25 more years. Plus at least Fisher ran the A’s well before he went off the deep end. Despite a World Series ring, the White Sox are a perpetual dumpster fire of an organization. The players of two professional teams have openly hated him for 5 decades. More fans would too if they read Lords of the Realm by John Helyar and The Game by Jon Pessah, the two definitive books on the behind the scenes business of baseball. Reinsdorf comes off as the villain in both. I can’t imagine baseball (and basketball) as a whole and the White Sox in particular wouldn’t have been better off for having never had him in charge.

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