5 Cheapest Owners in MLB

New York Mets owner Fred Wilpon
New York Mets owner Fred Wilpon / Paul Bereswill/Getty Images

During the contentious MLB labor negotiations meant to finally get the 2020 season started off properly, the true colors of many MLB owners are being shown to the public at large for the first time. Many of them are clearly putting profits before either the quality of the on-field product or the satisfaction of their fans. Even amongst a group of 30 greedy billionaires, there are some that rise above the rest due to their miserly ways.

Honorable mentions like Peter Angelos of the Baltimore Orioles came close, but these five cheapskates are the worst MLB has to offer.

5. John Henry, Boston Red Sox

Boston Red Sox owner John Henry
Boston Red Sox owner John Henry / Billie Weiss/Boston Red Sox/Getty Images

Henry is in charge of one of the league's gold star franchises, consistently has a competitive roster, and is in a major media market with a rabid fan base, You'd think he'd be the last one to trade a generational talent like Mookie Betts in the name of saving a few bucks. Cutting pay for anyone making over $50,000 when Henry has more than enough financial backing to avoid cutting costs in such a dramatic fashion is somehow magnitudes worse. We're not sure how we got here, but Henry has changed tremendously over the past several seasons.

4. John Fisher, Oakland Athletics

Oakland Athletics owner John J. Fisher
Oakland Athletics owner John J. Fisher / Michael Zagaris/Getty Images

Fisher is worth over $2 billion, yet he runs his team like he's the manager of an independent league team on a shoestring budget. He's piggybacked on Billy Beane's Moneyball approach to the point where Oakland is a complete non-factor in free agency. Fisher not only cuts costs on the field, but he's not even above trying to use the coronavirus pandemic to avoid paying rent on the Oakland Coliseum. As long as he is in charge, the A's will operate like a Triple-A team financially.

3. Jerry Reinsdorf, Chicago White Sox

Chicago White Sox owner Jerry Reisndorf
Chicago White Sox owner Jerry Reisndorf / David Banks/Getty Images

If you're not willing to pay Michael Jordan and Scottie Pippen, as evidenced in "The Last Dance," you're not going to suddenly turn into George Steinbrenner with your baseball team. Reinsdorf has spent years cutting costs and accumulating prospects with the White Sox, while Theo Epstein and the rival Cubs added elite talent and won a championship. The White Sox did reverse course over the last few years, making a run at Manny Machado while signing the likes of Yasmani Grandal and Edwin Encarnacion in free agency, but that splurge only took them to 18th in overall payroll, which is still below average.

2. Fred Wilpon, New York Mets

New York Mets owner Fred Wilpon
New York Mets owner Fred Wilpon / Jim McIsaac/Getty Images

Wilpon and his son Jeff might be the most notoriously bad owners/decision-makers in the league, and it's not hard to see why. Between not going after big-name free agents and paying average players marquee money, it's not hard to see why the franchise is in a disastrous place. If you wanted to make a textbook on how NOT to run an MLB organization in a major media market, from the financial end to the day-to-day operations, one need look no further for content than the Wilpons.

1. Bob Nutting, Pittsburgh Pirates

Pittsburgh Pirates owner Bob Nutting
Pittsburgh Pirates owner Bob Nutting / Joe Sargent/Getty Images

The Wilpon family is comical in how inept they are at running an MLB team, but Nutting is more on the despicable side of things. His payroll is egregiously low once again, as the Pirates are paying out just $48 million to players on the 26-man roster, which is less than just Gerrit Cole and JA Happ make by themselves. Beyond showing no interest in spending money to make the Pirates good, Nutting also used the pandemic as an excuse to get out of paying into employees' 401k benefits and retirement benefits. It's hard to find one thing Nutting hasn't screwed up.