Phillies owner shades Red Sox owner ahead of Dave Dombrowski-driven World Series

PHILADELPHIA, PENNSYLVANIA - OCTOBER 23: Philadelphia Phillies owner John Middleton lifts the Warren C. Giles trophy after the Phillies defeated the San Diego Padres in game five to win the National League Championship Series at Citizens Bank Park on October 23, 2022 in Philadelphia, Pennsylvania. (Photo by Tim Nwachukwu/Getty Images)
PHILADELPHIA, PENNSYLVANIA - OCTOBER 23: Philadelphia Phillies owner John Middleton lifts the Warren C. Giles trophy after the Phillies defeated the San Diego Padres in game five to win the National League Championship Series at Citizens Bank Park on October 23, 2022 in Philadelphia, Pennsylvania. (Photo by Tim Nwachukwu/Getty Images) /

On Friday night, the Dave Dombrowski World Series begins.

Dombrowski, the only GM-type executive to lead four different teams (Marlins, Tigers, Red Sox, Phillies) to the Fall Classic, drafted some of the best talent on each side of this year’s championship round. Justin Verlander, Nick Castellanos, and the injured Corey Knebel were all selected by the Detroit during Dombrowski’s tenure.

It’s also a Red Sox-heavy series. In addition to Dombrowski, Sox fans will be watching for Kyle Schwarber and Christian Vázquez.

To this day, or rather, yesterday when he spoke to USA Today, Dombrowski remains bothered by how his time in Boston came to an end:

"“I don’t think I was treated right. It hurt. It didn’t end the way I hoped or was handled.”"

How it was “handled” was an unceremonious dismissal right at the beginning of a Sunday Night Baseball game between the Sox and Yankees at Fenway on September 8, 2019.

While the Sox are still benefitting from Dombrowski’s drafting and signing expertise, their decision to abruptly fire him less than a year after their own championship in 2018 is back in the headlines because of his current success. In less than two years at the helm in Philadelphia, Dombrowski led a team that hadn’t even made the playoffs since 2011 back to the World Series for the first time since 2009. Understandably, as the Phillies surged deeper into October, many questioned the Sox’ decision to cut ties.

Phillies owner John Middleton doesn’t understand why Red Sox fired Dave Dombrowski

In the same article, Phillies owner and managing partner John Middleton had no problem throwing some light shade Boston’s way for freeing up Dombrowski:

"“I still don’t have any idea why John Henry fired him. I really don’t understand it. But I’m grateful he did. We wouldn’t have Dave Dombrowski and we wouldn’t be in the World Series.’’"

And when the Phillies won the pennant last weekend, the managing partner, who is also the team’s biggest fan, told Jayson Stark of The Athletic (subscription required) that he is appreciative of his new exec “every minute of every day”:

"“I think about Dave Dombrowski being a good choice every minute of every day, because he’s great. He’s historically great. I mean, before today, he was the only (general manager/president of baseball operations) ever to take three different teams to the World Series. Now he’s taking four. Nobody else has ever taken more than two different teams to the World Series. But Dave has done that over 30 years, and he’s had success everywhere. He’s just so incisive in what he sees in an organization with people — and he’s so decisive in acting on what he’s learned. It’s just spectacular.”"

In order to get the Phillies to October, they exceeded the luxury tax threshold for the first time in franchise history. In the past, Middleton said he was open to going over the limit for the right player. In this regard, he again endorsed Dombrowski:

"“It was Dave’s judgment. And when a guy has taken three other teams to the World Series before you, you’ve got to trust that man’s judgment.”"

The Sox were absolutely focused on winning when they hired Dombrowski in August 2015, letting him trade and spend to contend. But after extending Chris Sale, Nathan Eovaldi, and Xander Bogaerts in early 2019, they tied up the purse strings. Months later, Dombrowski was gone.

That’s why Middleton says it wasn’t easy to convince Dombrowski to take the job:

"“It doesn’t take a lot of time to interview Dave Dombrowski,’’ Middleton said. “It wasn’t whether Dave is good enough person to get the job. I had to convince the man to come back and help me. He wants to know, ‘Does this guy want to win? Is this guy pinching pennies to pay a 20-year-old rookie $500,000 instead of a good, competent veteran that cost $5 million?’ “I told him, ‘You have a lot of latitude here. I’m prepared to lose money. I’m prepared to lose a lot of money. I just want to win.’’’ Most important, Middleton stressed, you can trust him. Just ask around. “The biggest thing was that he needed to be reassured,’’ Middleton said, “having been burned in Boston. When you win the 2018 World Series title, and you’re fired the following August, you can’t go through that process and have it not affect you psychologically and emotionally. Dave needed to know that he wasn’t going to walk into a situation where I was going to flip on him.”"

In Middleton, it seems Dombrowski has found the perfect ownership fit: they are kindred spirit in their willingness to do what it takes to win. It’s not hard to find people who love baseball, but rare is the owner who loves his team enough to actually spend to make it a magical experience for the people who pay to watch it. There is absolutely no doubt that Middleton, a Pennsylvania native who first bought into the franchise in 1994, is a fan of the team he owns. He can often be found wandering around Citizens Bank Park, chatting with fans and posing for photos. By comparison, John Henry hasn’t sat and fielded questions from the Boston media in nearly three years.

Ultimately, ownership reigns supreme, but it’s clear from looking at front offices around the league that owner and executive need to be aligned in order to build a successful club. The Yankees are proof of that in reverse, as they reportedly plan to bring back Brian Cashman and Aaron Boone, for some reason.

The issue that Sox ownership faces now is that people no longer believe they’re committed to winning. The concern emerged as early as weeks after they fired Dombrowski, when Henry explained the decision:

"“Right after the World Series, I think it became clear to me that perhaps we weren’t going to be on the same wavelength going forward. But I was hopeful throughout the year, that maybe that perception would change. It didn’t.’’"

Dombrowski is a human being with strengths and weaknesses like everyone else, but no one can ever doubt his desire to win. So Henry stating that they were no longer ‘on the same wavelength’ makes it pretty clear that it was ownership, not executive, who shifted priorities.

In the post-Dombrowski era, the Sox have finished at the bottom of the division twice in three years. 2021 was an unexpected and pleasant surprise, not a concerted effort to contend. And while the Sox did exceed the luxury tax threshold in 2022, it wasn’t for any worthwhile reason.

It’s time for this ownership to change wavelengths again. If they need a reason, they should look no further than Dombrowski’s Phillies in the World Series.