5 Worst Major League Baseball Owners

William Pitts
Baltimore Orioles owner/cryptkeeper Peter Angelos
Baltimore Orioles owner/cryptkeeper Peter Angelos / Doug Pensinger/Getty Images

Owning a sports team is a relatively thankless task...well, other than the piles and piles of cash, of course. It's a high-profile position, so the owner's name is bound to be passed around a bit, but if that owner's name more well-known to fans than any of the players or managers, it's a good bet that the owner isn't popular or has overstayed their welcome. Here are five owners in Major League Baseball who definitely fit that description.

5. Fred Wilpon, New York Mets (since 2002)
Wilpon spent a number of years up financial creek without a paddle, largely thanks to the money he lost in Bernie Madoff's Ponzi scheme. This should be a good indicator of how wisely this man spends his money. Other scam artists Wilpon contributed to include Jason Bay, Luis Castillo, Kaz Matsui, Oliver Perez, and an aging Moises Alou.

4. Bruce Sherman, Miami Marlins (since 2017)
Derek Jeter may be the public face of the ownership group, but Bruce Sherman is the majority stakeholder with 46 percent.
Marlins fans (those of you who are left, anyway) hoping for a culture change anytime soon, don't get your hopes up. As soon as Sherman took charge of the team in 2017, he immediately got to slashing the Marlins' payroll - already one of the lowest in the big leagues - at the same time his new, $10,000,000 mansion was under construction in Boca Raton. Meanwhile, at baseball's newest park, attendance is routinely at half-capacity and people have stopped caring.

3. Bob Nutting, Pittsburgh Pirates (since 1996)
Even if he didn't invent the idea of using "small-market team" as an excuse for not ponying up for a contending roster year after year, we're sure he's brought it up at owner's meetings. Either way, Nutting's popularity figures are lower than dirt. After he failed to retain Andrew McCutchen, a local hospital pulled its advertising in protest from a newspaper that Nutting's company also owns. In October, Pittsburgh mayor Bill Peduto promised citizens he would look into legal options on how to have Nutting replaced as owner. And no, the office of mayor was not up for election in Pittsburgh in November, so it wasn't an attempt to win votes. When your poor ownership is a hot-button civic issue, maybe you should just leave of your own volition.

2. Jerry Reinsdorf, Chicago White Sox (since 1981)
Bulls fans may know him as the tight-fisted owner whose abrasive management style reduced the second MJ/Pippen/Jackson three-peat dynasty to a laughingstock in the space of a year. White Sox fans have pointed the finger squarely at Reinsdorf for their 11-year playoff hiatus, their inability or unwillingness to bring in top free agents (missing out on both Bryce Harper and Manny Machado last year didn't help), and their unpopular stadium...whatever it's called now. While the White Sox may hit it big in 2020, that's exactly what they said about the White Sox in 2019, and that didn't quite happen.

1. Peter Angelos - Baltimore Orioles (since 1993)
There are entire volumes that could be written on Angelos' incompetent, almost actively malicious butchery of the Baltimore Orioles' organization, so I'll keep it short. He took over a playoff-contending team in a fresh new stadium and reduced it to a laughingstock which has made the playoffs three times in the past 22 seasons.
He resented what he saw as the intrusion of the former Montreal Expos into his television market, and was the only owner to object to their move to Washington, so he drew up a television contract in which the Orioles pocketed hundreds of millions of dollars of the Nationals' television revenues from MASN - which the O's own. Now there are rumors afoot that the Orioles may move to Nashville...rumors that Angelos has strictly denied, but Baltimore has heard the same noise before, and Camden Yards' lease is up at the end of the 2021 season.