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Playoffs show how fickle Brian Cashman’s offseason can be

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Two teams well represented in these playoffs symbolize just how difficult it is to win a championship. The Dodgers, obviously, are one. Kirk Gibson was…
Two teams well represented in these playoffs symbolize just how difficult it is to win a championship.
The Dodgers, obviously, are one. Kirk Gibson was part of the first-pitch ceremony before Game 4 at Dodger Stadium, and Orel Hershiser was the man for Game 5. The Dodgers lost both games and the World Series and remained without a title for 30 years, since the 1988 team inspired by Gibson and Hershiser. This despite a few billion dollars invested in payroll, large stars and being the only team to make the playoffs each of the past six years and the World Series the last two.
The other exemplar is the 2011-14 Tigers. This postseason was filled with their alumni, notably starters. That was still a point when it was believed no asset was more vital to October success than a strong rotation. And those playoff teams had some combination of Rick Porcello, David Price, Anibal Sanchez and Justin Verlander — who all started in the just-concluded playoffs — plus Max Scherzer, who in the coming weeks will finish in a Cy Young top five for the sixth straight year.
“I run into guys from that team all the time and they all say a version of the same thing, ‘How did we never win it?’” said Dave Dombrowski, who was those Tigers’ GM. “It is hard to explain. We got there every year, but something always came up.”
Dombrowski is the Red Sox’s president of baseball operations now. He inherited Porcello, lured Price with the largest pitching deal ever, plus signed J. D. Martinez and traded this year for Ian Kinsler, who were both parts of Tigers lineups that at various points also included Miguel Cabrera, Victor Martinez, Torii Hunter and Prince Fielder.
“I think that team shows how tough it is to win,” Dombrowski said.
The most common theory about why those Tigers teams never won it all was that Dombrowski could never assemble a strong enough pen. He heard that same criticism this season, that he had left vulnerable a historic club by not adding a Zach Britton, Jeurys Familia or Brad Hand in July.
Yet, the bullpen ended up being a Red Sox strength in the postseason because Matt Barnes and, particularly, Joe Kelly raised their performance, and manager Alex Cora aggressively used starters in relief, none more prominently than Nathan Eovaldi, who was an in-season add by Dombrowski.
That helped Dombrowski, Porcello, Price, Kinsler and Martinez win the championship together in Boston that had eluded them in Detroit. It also shows how tricky getting a parade is.
I mention this because there will be a lot of criticizing and critiquing that the Red Sox were able to win and the Yankees weren’t. That is a fact. No escaping it. The Yankees have now been eliminated by the eventual champs the past two years. You could make a case the Yankees played the Red Sox tougher in the playoffs than the Astros or Dodgers. Each won just one time in their playoff round against Boston, the Yanks in just a best-of-five, and Gary Sanchez came within what, 5 feet, in the ninth inning of Game 4 of forcing a decisive game.
Eovaldi and World Series MVP Steve Pearce were the kind of in-season adds you could denounce the Yankees for not making, except that J. A. Happ and Luke Voit actually outperformed Eovaldi/Pearce after their July Yankee adds.
The Yankees, like the Dodgers, have been in the tournament with a chance to win, but didn’t. They will need to figure out why because as Dombrowski said: “Winning one makes a difference.… It is significant how you feel and how you are viewed [if you win one].” It changes perceptions, rewards, historic status.
Think about the Cubs and Astros ending long title droughts recently compared to the Dodgers and Nationals extending their title misery. Chicago and Houston have those titles no matter what else happens in this period in which they are among the super teams.
You think the window will stay open for these kind of teams. But you blink, and suddenly Stephen Strasburg is 30 and Bryce Harper is a free agent. Clayton Kershaw has lost some of his fastball and is mulling an opt-out.
At his end-of-season press conference, Brian Cashman said: “Nobody knows how long a window stays open and nobody cares about windows. They [fans] care about world championships.”
So the offseason begins in earnest now with the World Series over and Cashman trying to deduce what would take his team from good, but not good enough, to last standing. There are no easy answers. Those great Tigers teams never figured it out. The Dodgers — despite all their assets — are at 30 years and counting.
Dombrowski never fixed his pen in Detroit and failed to win, didn’t address it this year in Boston and won nevertheless. As he said, it is tough to win. But teams will keep trying this winter to make their teams good enough because when you don’t, the pain lasts forever.

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