Philly Front Office

The rabbit hole of worst owners in baseball runs pretty deep. These 5 didn’t make the cut for the big list but deserved special mention for their foul deeds.

These 5 are in no particular order.

• Boston Red Sox – John Henry and Fenway Sports Group: John Henry has won 4 World Series titles. He has objectively been great for the Red Sox, especially when you factor in their lack of titles before he got there. BUT…there is that little matter of the last few seasons beginning with the 2020 trade of Mookie Betts. Fenway Sports Group is flush with an absurd amount of cash and assets including everything Red Sox (including Fenway itself and NESN), multiple professional sports teams and their stadia, and even the Boston Globe. Despite this, in 2020 the team basically salary dumped the remaining 3/$96m of David Price’s salary and the $27m it owed Betts for nothing. Betts was 27 and coming off his 4th consecutive MVP level season. Instead of being the team to give him the $300m+ contract he deserved, they simply gave him to the Dodgers for salary relief. 3 years later they gave that money to Rafael Devers instead, probably a similar caliber hitter, but with vastly inferior defense and utility. On top of this, the team has seen its payroll ranking drop considerably, routinely between $100m and $150m behind the top spenders in the game. Despite all their success, a desire to save cash robbed Red Sox fans of an all-time great in Betts.

• San Diego Padres – John Seidler, not Sheel Seidler: The previous owner, Peter Seidler, was awesome. He spent his ass off to try to bring excitement and a winner to San Diego. He is the kind of owner any team would love to have. Since his death in 2023 though, things have changed. His widow, Sheel Seidler, has since filed a lawsuit claiming that Peter’s brothers have taken control of the club against his wishes and engaged in self-dealing using the Padres as their personal slush fund. She presented an allegedly handwritten document labeling her and her children as the ones to be in control of the team. Basically, she is alleging that they suck and are not doing their jobs as trustees, while they are denying it and calling her greedy. This thing is probably going to arbitration so we won’t be able to hear too much about it, but the proof is in the pudding. A year after his death, payroll went way down. The next year it was up from the previous year, but mostly because they had no choice in the matter due to contract obligations already in place. We’ll see if anything comes from this, but it’s a shit situation from an organization that had just become relevant.

• Los Angeles Angels of Anaheim – Art Moreno: It is hard to really fathom how badly this organization must be run. They have won 4 MVP trophies and employed two of the greatest players EVER in the last 10 years with no playoff appearances to show for it. They haven’t even been above .500 in that time. It isn’t from lack of spending either since they are routinely ranked in the top 10 for payroll. They have even shelled out some of the highest individual contracts of all time in Albert Pujols, Mike Trout, and Anthony Rendon. The owner has a fat wallet and wants to win, but they are just flat out terrible. That can only be from complete mismanagement. I guess we shouldn’t expect very much from a team that claims to be from two cities. Why not just go back to California Angels? It’s better than LAAoA. (Still better than [no city] Athletics)

• Washington Nationals – Mark Lerner: I don’t think the Nationals are poorly run, I think they are deceptively run. They have had a lot of success under Ted Lerner’s ownership and even shelled out the requisite cash to keep World Series hero Stephen Strasburg in the fold. Everyone else, not so much. Trea Turner apparently wanted 6/$100m early on and they wouldn’t give it to him. 2 years later when he asked for Francisco Lindor’s 10/$341m contract they simply refused to negotiate and traded him away. They made 3 low ball offers to Juan Soto that topped out at 15/$440m. That seems like a lot of money, but it was heavily backloaded (reducing the present day value) and came in at just under $30m a year. Just the AAV would have had him ranked about 17th in the league, but depending on how backloaded the deal was would have been far worse for ALL of those 15 years. The worst deception is Bryce Harper though. Nationals fans hate him for turning down the team’s $300m offer while completely ignoring that $100m of that was to be paid out at $4m a year for 25 years after the contract ended, essentially nuking its present day value. It was a joke of a deal, but has succeeded in making Harper a pariah in the capitol.

• Cincinnatti Reds – Bob Castellini: Castellini is about as close to the bottom 5 as you can be without going over. The only thing holding him back is that his son is the dipshit and not him. Son Phil famously asked “where are you going to go?” when a radio show asked him what fans should think of the team when they are so bad and regularly gets disgusted at guaranteed contracts for players. Bob isn’t off the hook though. His main problem is simply that he doesn’t have enough money to own and operate a professional baseball team. He has owned the team for 20 years but with a net worth of $400m, he can’t afford to ever splurge on the team or lose money. He’s walking a financial tightrope. It wouldn’t be the worst idea for him to get some investors. Expect his dumbass kid to simply sell the team once the old man passes away. The Reds do have some up and coming talent and Elly de la Cruz in the mix, but expect the Elly trade rumblings to start some time after next season when he first hits arbitration.

There are other incredible ownership tales out there like George W. just wanting to be commissioner and becoming President instead, Charlie O’ Finley selling a champion for cash to avoid free agency, everything Jeffrey Loria did to the Marlins, and Marge Schott’s existence but those are for another time.