If there is one thing that Tom Ricketts has been great at, it's finding a way to step in it with his comments at the worst possible time.
In recent years, Ricketts hasn't been shy about making comments that have drawn the ire of Cubs fans. Just this past offseason, while promoting the Cubs Convention, the Ricketts foolishly stated the goal each season was for the team to "break-even" financially.
For a team that is in one of the largest markets in Major League Baseball, Ricketts' comments were perceived as being incredibly tone-deaf. And, that has been a theme for the Cubs' chairman this offseason. Especially when the Cubs' franchise value continues to climb.
Not to be outdone with his comments this past offseason, Tom Ricketts recently had an interaction with noted Cubs content creator, SetupManBrian, and the exchange was a laughably bad look for the Cubs' owner.
So my interaction with Tom Ricketts..
— Brian (@SetupManBrian) May 31, 2025
Me: What’s something as fans we don’t understand? Like from a business perspective?
Tom: that teams lose money all the time and we are just trying to break even.
( yes he used the infamous line)
Me: How can I help make that better? What…
Another embarassing moment for Tom Ricketts
Here you have the chairman of the Cubs speaking to a fan above anything else, and he chooses to double down on his belief that the goal for each season, from a financial side of things, is to break even.
Anytime that Ricketts elects to push his "break-even" motto, it's an insult to every Cubs fan. The reason is that the Cubs are not losing money. The difference, the one Ricketts doesn't believe Cubs fans know, is that the Cubs, if they do lose money in a particular season, are taking losses on revenue. In other words, by the end of the season, the Cubs may not make as much money as they projected at the start of the season. However, the key part is that the Cubs are still coming out ahead. Which, to circle back to what has already been stated, the Cubs' franchise value under Ricketts has only gone up. However, their spending does not match that.
If we left it just there, that would be enough for Cubs fans to once again realize that Ricketts will be the villain when there is a potential work stoppage for Major League Baseball after the 2026 season, But, again, let's remember that Ricketts likes to drive the point home that he can't read the room. Hoping to find common ground with Ricketts, Brian asks what fans can do to improve the perception Ricketts' has, and the reply he had was for fans to say nice things about the team online.
It seems unlikely that Ricketts will get his wish. Fans are not yes-men, nor should they be. Ricketts has been trying to pull the wool over the fanbase's eyes for far too long. The only thing that has changed now is that Ricketts isn't afraid to be more direct with his nonsense.
