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Behind the Seams: All the Pressure is on Dave Dombrowski to Deliver the Red Sox a World Series

By Tony Massarotti, 98.5 The Sports Hub

Dave Dombrowski has a big name and a big reputation, and he is clearly not afraid to make a big trade. But for all the buzz that has seemed to accompany Dombrowski throughout his career as a major league executive, there has been something decidedly lacking.

Championships.

Has Dombrowski won a title? Well yes, with the 1997 Florida Marlins. That was 21 years ago - and with a team that was largely bought thanks to a dramatic payroll increase. But fine. Titles are titles are titles. And yet, Dombrowski hasn’t won since, something that can’t (and shouldn’t) be overlooked as the Red Sox embark on the second half of the 2018 season tonight following a first half in which the Red Sox (68-30) steamrolled to the best record in baseball.

So here’s the question: can Dombrowski seal the deal or not?

Apr 13, 2018, Boston, MA, USA: Boston Red Sox president of baseball operations Dave Dombrowski talks on the phone prior to a game against the Baltimore Orioles at Fenway Park. (Photo Credit: Bob DeChiara-USA TODAY Sports)
Apr 13, 2018, Boston, MA, USA: Boston Red Sox president of baseball operations Dave Dombrowski talks on the phone prior to a game against the Baltimore Orioles at Fenway Park. (Photo Credit: Bob DeChiara-USA TODAY Sports)

Fact: Since Dombrowski last won a world title, Theo Epstein has won three – two with the Red Sox and one with the Chicago Cubs. Brian Cashman, the general manager of the Yankees, has won four. San Francisco Giants general manager Brian Sabean has won three titles, wiping out Dombrowski’s Tigers in a four-game sweep in 2012.

In fact, not only has Dombrowski failed to win a title during the last 20-plus years, he really hasn’t gotten all that close. Dombrowski’s teams have made the playoffs only eight times to date in his 29 seasons. And on the two occasions since 1997 that his clubs have reached the World Series, Dombrowski’s teams are 1-8, losing the 2006 World Series to a St. Louis Cardinals club that won a laughable 83 games. (Dombrowski’s Tigers went 95-67 and lost in five games.)

Oh, and did we mention the collapse of Dombrowski’s Detroit Tigers in the 2013 American League Championship Series? Somehow, the Tigers didn’t have a legitimate bullpen. And it cost them when David Ortiz hit that unforgettable grand slam in the final innings of Game 2.

So here we are now, in Dombrowski’s third full season with the Red Sox as the club approaches the trade deadline, and the Red Sox look a lot like Dombrowski’s teams of the past. They could be on their way to their third straight division title, and yet they are 1-6 in the last two postseasons. The Cleveland Indians added a bullpen piece on Thursday that the Red Sox reportedly coveted in San Diego Padres left-hander Brad Hand, and the story isn’t so much that the Red Sox missed out on the player so much as it is that they may not be able to do anything about it going forward.

Mar 4, 2018; Sarasota, FL, USA; Boston Red Sox president of baseball operations Dave Dombrowski prior to the game against the Boston Red Sox at Ed Smith Stadium. Mandatory Credit: Kim Klement-USA TODAY Sports

We all know the problem with Dombrowski’s go-for-broke approach, whether it be in Florida, Detroit or Boston. What happens if you don’t win? In adding to an organization that included – before Dombrowski got here – Mookie Betts, Xander Bogaerts, Jackie Bradley, Dustin Pedroia, Rafael Devers and others, Dombrowski has effectively backed the Red Sox into a corner. Incredibly, the Red Sox now have seemingly little in the way of young talent (read: prospects) or financial flexibility, a double dose of reality that left the Red Sox outclassed and outgunned in the talks that delivered Hand to Cleveland.

Does that mean Dombrowski will be left empty-handed by the time all the trade dominoes have fallen? Not necessarily. He’s an experienced executive. He undoubtedly has something up his sleeve. The ultimate question is whether that will be enough to put the Red Sox – and Dombrowski – over the top, because we all know that the Red Sox, incredibly, have not won a playoff series in a season other than 2013 over the last 10 years.

The clock has been ticking for a long time now on this nucleus of Red Sox players.

And is ticking most loudly for the man who has built the team around them.

You can hear Mazz weekdays from 2-6 p.m. EST on the Felger & Massarotti program, and from 6-7 p.m. on The Baseball Reporters. Follow him on Twitter @TonyMassarotti.