Boston Red Sox relief pitcher Ryan Dempster (46) is congratulated by catcher David Ross after the Red Sox defeated the St. Louis Cardinals, 8-1, in Game 1 of baseball's World Series Wednesday, Oct. 23, 2013, in Boston. (AP Photo/Matt Slocum) ORG XMIT: WS289
ST. LOUIS — Fifteen years, five months and 2,395 innings after he made his major-league debut, Ryan Dempster struck out Matt Adams to finish off a Game 1 victory in his first World Series last week at Fenway Park.
“After that game, back in the clubhouse, I probably had an ear-to-ear grin for five or six hours,” said the longtime Cub, who signed a two-year deal with the Boston Red Sox a few months after the Cubs traded him to the Texas Rangers last year.
“When you look back, you think at some point of your career you were going to go to the playoffs and get a chance to go to the World Series,” Dempster said. “And going through this experience, I think you realize how hard it is to really get there, collectively as a team and as an individual being on the right team that you can help make that happen.”
Dempster makes a point that figures to resonate through the Cubs’ most important order of business this offseason — if not haunt them.
That would be trying to sign Opening Day starter Jeff Samardzija to a multiyear extension. Without it, the arbitration-eligible pitcher is certain to be dealt by the trading deadline next summer — if not shopped this winter.
Sources say an extension looks like a long shot at this point, with neither side confident a sizable gap in their thinking can be closed when talks restart in earnest this winter.
Samardzija, 28, has said repeatedly that sheer dollars will not be the primary factor for a guy who already has made more than $17 million in his career. But neither side anticipates a hometown discount, either, and Samardzija has said — and shown — he’s confident enough to go year to year and test his value as a free agent after the 2015 season.
That would force the Cubs to trade him in the next eight months before his trade value drops dramatically in his final year of club control.
The wild card in the process goes back to what Dempster talked about.
Samardzija, a Notre Dame football star who didn’t get his national championship there, wants to win. Big. And soon.
“That’s what it’s all about,” Samardzija said as he closed out a 200-inning, 200-strikeout season that fell short of a winning record in large part because of the rebuilding project going on around him. “It’s not about playing six months. It’s about playing the seventh month. That’s it. Otherwise, you’re just out here biding time. So I want to win. I want to pitch in October, and that’s it.”
If the Cubs can’t persuade Samardzija that they have a plan that includes late-October baseball while he’s still a young man, they likely will lose him.
And if they don’t bring him back, it leaves them that much further from contending, considering that for all the high-end hitting prospects getting attention in the farm system, the Cubs don’t have the same kind of “can’t-miss” guys on the pitching side.
In fact, their decision to pass on power-armed college pitcher Jonathan Gray in June to draft college slugger Kris Bryant — after significant organizational debate — could indirectly affect the Samardzija talks.
If impact pitching were coming up fast in the system, it would be easier to project a competitive timeline.
Dempster, an Arizona workout partner and good friend of Samardzija’s, has an idea what his former teammate faces. But offers no advice.
“Jeff’s a really smart kid, man. He works really hard and understands both sides of baseball,” Dempster said. “The playing side and the business side. …
“I think first and foremost he wants to win in Chicago. I think that’s really important to him. He has a chance to be a leader there. But he has a chance to be a leader on a winning team. And who doesn’t want that?”