The Cheapskate Hall of Fame

It’s pretty tough out there these days. Thanks to things like high inflation and job layoffs, a lot of us are struggling to make ends meet. Even the 1% are feeling the pinch (have you seen the price of Bentleys and Kobe beef lately?!), which could explain why even the upper crust is looking to cut costs.

For example, new Portland Trail Blazers owner Tom Dundon has been in the news lately not for overseeing a surprisingly successful season that started with the firing of head coach Chauncey Billups, but because of some odd tactics to reduce expenses.

Dundon – who is worth around $2 billion – decided to cancel T-shirt giveaways for fans before home playoff games. For road games, staff were instructed to leave hotels early to avoid late checkout fees. At least they got to go; the Blazers’ two-way players weren’t permitted to fly out with the team, and neither were their longtime digital reporter and photographer. The traveling masseuse also had to stay home.

While these are perhaps a little ticky-tack, more concerning to fans (aside from not getting a cheap shirt) is the fact that Dundon doesn’t seem to understand the importance of a head coach and why they need to be adequately compensated. Even worse – some are speculating that he’ll move the team.

Dundon is far from the only team owner who has gone to great – and often silly – lengths to save a buck. Here are some others who deserve their own place on the list of world-class penny-pinchers.

Connie Mack

It’s safe to say that as an MLB manager, Mack’s numbers will probably never be beaten. He holds the all-time records for wins, losses, and games managed. During the half-century in which he managed the Philadelphia Athletics, he was also one of the owners, and to call him frugal is a bit of an understatement. While he built great teams, he would just as quickly dismantle them, and he’s quoted as saying: “The best thing for a team financially is to be in the running and finish second. If you win, the players all expect raises.” There has even been speculation that the team purposely lost the 1914 World Series because of Mack’s death grip on the purse strings.

William Baker

In 1913, Baker purchased the Philadelphia Phillies, and things looked promising pretty quickly, as the team made it to the World Series in 1915. It wasn’t long, however, before Baker wore out his welcome and the team quickly descended into decrepitude, spurred on by his decision to sell future Hall-of-Famer Grover Cleveland Alexander to the Cubs instead of increasing his salary. And here’s another fun little tidbit: Baker refused to pay people to cut the grass at his stadium, instead using a flock of sheep to do it.

Charles Comiskey

Where to begin with this guy? A notorious racist, Comiskey was instrumental in keeping the color line firmly entrenched in baseball. On top of that, even though he was quite wealthy, he was infamously cheap. For example, he wouldn’t pay to have his players’ jerseys laundered, making them do it themselves if they wanted clean uniforms. The 1919 Black Sox scandal has been at least partially attributed to Comiskey’s reluctance to pay his players decent salaries.    

George Halas

Halas’ contributions to the NFL are many. In addition to helping start the league, he also founded the Chicago Bears and was instrumental in getting Lambeau Field built for the Green Bay Packers. But, because he’s on this list, you know there’s some cheapness coming. In 1933, to save money, Halas fired his head coach and took over the helm himself. He also made players share hotel rooms – and sometimes beds – on road trips. Mike Ditka, who played for Halas, said about his coach: “He throws nickels around like manhole covers.”

Marge Schott

Something tells me that Schott and Comiskey would have been fast friends if their paths ever crossed. The instances of Schott being a horrible person are plentiful, and there were several times in which she revealed herself as a racist, including repeated praise of Hitler. She was also extremely cheap and would scrimp everywhere she could with the Cincinnati Reds. Said former player David Wells:

“This woman was psycho. She’s nuts — cheap as can be. You had to go in, if you wanted a pair of socks or sleeves or stirrups, whatever it was, you had to go up in her office, and it was like a cave in there … you had to buy them from her … And then we’d get our meal money, and we’d have pennies and nickels and dimes in it.”

John Fisher

If there was ever an instance of life imitating art, it’s John Fisher and the A’s, who appeared to take ownership lessons from the movie Major League. Once it became clear that the city of Oakland wouldn’t use taxpayers to fund a new stadium (Fisher really needed that money, as his net worth is only around $3 billion), he seemingly implemented cost-cutting measures to force a move. He did this by trading good players and slashing payroll. He also drastically reduced the team’s analytics and scouting departments. In addition, he refused to make significant improvements to the Oakland Coliseum and didn’t seem terribly concerned with possums calling the stadium home.

These are just the most egregious examples of owners being spendthrifts, as sports history is riddled with them. And sure, anybody can be excused for trying to save some money, but if you’re worth more than the GDP of certain countries? There’s truly no excuse for that.