PHILADELPHIA — Years ago, before John Middleton became the face of the Phillies’ ownership group, Jimmy Rollins equated him with George Steinbrenner. It’s a comparison that Middleton never minded. Because the late Yankees owner was notoriously obsessed with winning, a trait that is admirable to a former college wrestler-turned-billionaire baseball owner.
And like Steinbrenner, Middleton usually gets his men.
The Phillies targeted Bryce Harper in the 2018-19 offseason and outbid everyone. Same with Zack Wheeler a year later, J.T. Realmuto the year after that, and Kyle Schwarber and Nick Castellanos eight months ago. Since 2018, they have spent more than $1 billion on free agents. Middleton pushed the payroll over the $230 million luxury-tax threshold this year. After coming within two wins of a World Series title, want to bet he’ll do it again?
