Owning a Major League Baseball team is a massive responsibility, but some owners seem to have missed that memo. From penny-pinching misers to chaotic decision-makers, these owners have torched fan hopes, alienated star players, and turned once-proud franchises into laughingstocks.
Some of them made baffling trades, others refused to spend money, and a few just didn’t seem to care about winning at all. Here are the ten most incompetent MLB owners ever.
10. Fred Wilpon – New York Mets
Wilpon oversaw decades of dysfunction, bad contracts, and bizarre front-office moves that left Mets fans permanently frustrated. To make matters worse, he got caught up in the Bernie Madoff scandal, which limited the team’s spending and kept them from building a true contender.
9. Frank McCourt – Los Angeles Dodgers
McCourt ran the Dodgers like a personal ATM, using team funds to fuel his lavish lifestyle while the franchise crumbled. His ugly divorce case turned into a battle for ownership of the team, and by the time MLB forced him out, the Dodgers were a mess.
8. Ken Behring – Seattle Mariners
Behring nearly destroyed baseball in Seattle when he tried to move the team to Tampa Bay despite the city’s growing love for the Mariners. His complete lack of interest in winning made him one of the most unpopular owners in baseball history.
7. Bob Short – Washington Senators/Texas Rangers
Short’s leadership was so bad that he managed to get two different cities to hate him. He ran the Washington Senators into the ground before moving them to Texas, where they struggled for years under his ownership.
6. Peter Angelos – Baltimore Orioles
Angelos was known for meddling with baseball operations despite having no clue what he was doing. His refusal to invest in analytics, scouting, and player development led to decades of losing, and Orioles fans suffered because of it.
5. Stuart Sternberg – Tampa Bay Rays
Sternberg took a team with passionate fans and constantly threatened to move them, refusing to invest in a proper stadium. While the Rays have been competitive, his unwillingness to spend money has kept them from reaching their full potential.
4. Vince Naimoli – Tampa Bay Devil Rays
Before the Rays were a model of small-market success, they were an unwatchable disaster under Naimoli. His penny-pinching ways and bizarre policies, like banning outside food and making employees pay for coffee, made him an infamous figure in baseball.
3. Jeffrey Loria – Montreal Expos/Miami Marlins
Loria managed to ruin not one but two franchises, first helping run the Expos into irrelevance before selling the team and buying the Marlins. He then gutted the Marlins’ roster multiple times and forced taxpayers to pay for a stadium he had no interest in filling with talent.
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2. Charles Comiskey – Chicago White Sox
Comiskey’s cheapness directly contributed to the Black Sox Scandal, as underpaid players were more tempted to throw the World Series. He is remembered as one of the most despised owners in history, proving that even in the early 1900s, bad ownership could sink a team.
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1. Harry Frazee – Boston Red Sox
Frazee made the worst trade in baseball history, selling Babe Ruth to the Yankees and triggering an 86-year championship drought for Boston. His decision-making not only cost the Red Sox dearly but also helped turn the Yankees into a dynasty, making him the ultimate example of an owner who destroyed his team’s future.
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