Dave Dombrowski signing Jordan Montgomery would be a heartbreaker for Red Sox fans

Jun 24, 2023; Philadelphia, Pennsylvania, USA;  Philadelphia Phillies President of Baseball
Jun 24, 2023; Philadelphia, Pennsylvania, USA; Philadelphia Phillies President of Baseball / John Geliebter-USA TODAY Sports

Dave Dombrowski is a polarizing figure from a prior Boston Red Sox front office. Dombrowski brought a World Series title to Boston in 2018 and was fired the following season after what seemed like an unprecedented downturn.

Despite helping to bring a championship to Boston, the former chief baseball officer left the Red Sox in a bit of a rough spot. He signed Chris Sale and David Price to huge contracts and famously neglected Boston's farm system — he helped create the hole that the Red Sox find themselves in this offseason and the few before it, although it must be said that he was also acting on ownership's instruction. And again, he won a World Series. That's the goal.

Now, Dombrowski is president of baseball operations for the Philadelphia Phillies and he's turned them into deep playoff contenders in the span of a few years. He's brought in Kyle Schwarber, Nick Castellanos, Trea Turner and others, in addition to extending Aaron Nola. There are reports that he's hoping to extend Zack Wheeler by Opening Day. But there's more.

The latest Phillies rumor could be the nail in the coffin for a lot of Red Sox Nation, as Dombrowski and Co. are reportedly interested in signing Jordan Montgomery. Given Dombrowski's record, Sox fans fear they might be able to get it done.

A potential deal with Montgomery has been Boston fans' last hope for the offseason. As the pitcher sits on the market, he's had time to consider his price. He may be forced to settle for a shorter-term deal than the one he's been asking for, which is rumored to be around six years.

Philadelphia's interest in Montgomery comes with the bet on the pitcher taking a shorter-term deal, so if the left-hander doesn't budge, a deal probably won't come to fruition.

Philadelphia has a lot of players signed long term — Harper, Nola and Turner are all on long-term, expensive contracts and could prevent the team from being able to afford Montgomery for more than two or three years.

Former Red Sox exec Dave Dombrowski could steal Jordan Montgomery from Boston

That's what Sox fans are banking on. Trading Kenley Jansen to save his 2024 salary and making the push for Montgomery could be the savior of Boston's coming campaign. The Red Sox could still likely finish the season at the bottom of the American League East again, but they would at least be competitive, or on their way there.

Boston's front office has been pushing a "waiting game" mentality on Sox fans all winter — there's no sense in trying to be competitive without the organization's top prospects in the bigs, according to the front office.

But there's no need to wait to be competitive, and Dombrowski's club shows it every day. He signed coveted players at their worth and now his team has pushed far into the playoffs two seasons in a row. There needs to be some Dombrowski mentality in the Sox front office.

fter the winter Boston fans have been put through, Dombrowski and the Phillies getting Montgomery would be the final blow on one of the worst MLB offseasons in recent memory, not just for Sox fans.

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