The Cleveland Guardians have been one of the best and most successful teams in baseball over the last decade.
Since 2016, they have been to the postseason a total of six times, with two AL Championship Series appearances and a World Series loss.
They have made moves to compete, even if most fans don’t feel that way.
However, 92.3 The Fan analyst Ken Carman explained that there is a difference between trying to win and trying to win it all.
The latter scenario implies making uncomfortable moves that might be risky, but will put the team in a position to compete with the elite, not just to make the postseason.
He doesn’t think Paul Dolan is a bad owner for the Guardians, but has serious doubts about his commitment to win a championship.
“(Dolan) is not an irresponsible owner… But he is not a guy who is going to make a very, very strong move to win it all,” Carman said in a heated discussion with Anthony Lima.
🚨"(Dolan) is not an irresponsible owner… But he is not a guy who is going to make a very very strong move in an effort to win it all."@KenCarman doubles down on his take from yesterday regarding the #Guardians ownership going for it all or not👀
🔊: https://t.co/EyN5flS0hz pic.twitter.com/RB8q664CxJ
— 92.3 The Fan (@923TheFan) July 17, 2025
In another video of the same discussion, Carman notes that only seven or eight teams in the league are trying to ‘win it all’ as opposed to just competing, with Lima repeatedly asking him to give him a number on what the Dolans need to spend to enter that upper echelon.
"It's more of a baseball problem… Give me a number, what do the Dolan's need to spend to win it all? I don't get an answer."@SportsBoyTony gives more push back to @KenCarman argument that the #Guardians have not done all that they can to win.👀
🔊: https://t.co/EyN5flS0hz https://t.co/pegBg3SZbN pic.twitter.com/1dcq0D2CQY
— 92.3 The Fan (@923TheFan) July 17, 2025
It’s hard to put a number on it, and it will always depend on circumstances and each specific offseason or market.
One thing is clear: when the Guardians make an unequivocal move to win it all, there will be a consensus among fans: everyone will know.
NEXT: Guardians Could Make Major Trade Deadline Moves








