Red Sox insider unites fans with organization's 'biggest mistake' of the last 5 years

Toronto Blue Jays v Boston Red Sox
Toronto Blue Jays v Boston Red Sox | Billie Weiss/Boston Red Sox/GettyImages

The Boston Red Sox's recent slide away from American League wild card contention has fans yearning for past successes — specifically, the Sox's highest of highs, the 2018 campaign.

Boston's most recent World Series-winning club featured generational talent and unexpected heroes. Nearly six seasons later, most of those players, and the man who put that team together, are long gone.

Dave Dombrowski constructed the 2018 Red Sox team in the model of the early 21st-century clubs. They were expensive, but the front office was hell-bent on fielding a winning club, and they became exactly that as the franchise's winningest squad of all time.

Less than a year later, Dombrowski was fired. Since, Boston's payroll and the number of MLB stars on the team have plummeted. Rafael Devers and Alex Cora are the last remaining pieces of 2018. Meanwhile, Dombrowski's Phillies have thrived.

Firing Dave Dombrowski has haunted the Red Sox as Phillies continue to improve

John Tomase, Red Sox insider for NBC Sports Boston, claims the organization's firing of Dombrowski was their biggest mistake of the last five years. Many Red Sox fans agree. John Henry and Fenway Sports Group probably don't.

When Dombrowski saw a weakness in his Red Sox club, he remedied it quickly and by any means necessary. From exorbitant spending to risky trades, Dombrowski did what he had to do to field a winning team. He's brought fan favorites and MLB icons to Philadelphia, like Zack Wheeler and Bryce Harper, and he extended homegrown talent like Aaron Nola.

Some fans take issue with such an approach with the prospect pool though, and the farm system was in rough shape when Dombrowski departed the organization. But he drafted a lot of quality talent he isn't credited enough for, like Triston Casas, Tanner Houck and Jarren Duran.

Henry and FSG likely took issue with his rate of spending. FSG began expanding at a faster rate after Dombrowski's dismissal in 2019 — it's owned Liverpool since 2010, and most of its investments were Red Sox or Liverpool-centric before 2019. Henry may not perceive Dombrowski's dismissal as a mistake, but as a smart move to save him some money on his already-profitable Red Sox club.

Either way, as Red Sox fans grow tired of fruitless offseasons, boring trade deadlines and years of playoff misses, they think back to 2018 and one of the greatest teams in the organization's history. And as the Phillies continue to improve by making big trades, signing expensive talent and extending fan-favorites, Boston's front office — and Sox fans everywhere — have a clear view of what could've been had they kept Dombrowski around.

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