Ryan Dempster won't play in 2014

FORT MYERS, Fla. -- Even as he talked to Boston Red Sox manager John Farrell about his decision to stop playing baseball, perhaps forever, the impish side of pitcher Ryan Dempster came to the surface, as it so often did in his 16 years in the major leagues.

"I joked with John a little bit -- 'Sorry, Skip, to throw this on you in the last minute, but you're going to have to find another Opening Day starter,'" Dempster said Sunday morning at a news conference where he announced he would not pitch in 2014.

Until about two weeks ago, when he called Farrell first, then general manager Ben Cherington to inform them of his thinking -- "It came out of left field," Cherington said -- the Red Sox had planned on Dempster coming to camp as one of six veteran starting pitchers competing for five spots in the rotation.

Instead, Dempster showed up Saturday to say a few goodbyes to teammates and staff, then make his announcement Sunday of his decision to step away from the game.

"I had an incredible run," said Dempster, who made his big-league debut with the Florida Marlins, spent the majority of his career with the Chicago Cubs, also played with the Cincinnati Reds and Texas Rangers, and finished by winning a World Series with the Red Sox. "I had a chance to play 16 years in the major leagues and be around a lot of great teammates, made a lot of good friendships -- great friendships -- a lot of great memories.

"But I just feel like where I'm at with my health, how I feel personally, I just feel like it's in the best interests of both myself and the organization and the team to not play this year. I don't feel like I can compete or produce the way I'm accustomed to."

Too much finality to the word "retirement?"

"Yeah, I think so," said Dempster, who choked up with emotion when his attention was called to the presence of all of his teammates who attended his news conference -- among others, the entire starting rotation, catcher David Ross and Dustin Pedroia.

"At the end of the day, if this is the end, this is the end, and what a great way to go out," he said, "and think that the last batter I faced was to strike out to end Game 1 of the World Series."

Dempster pitched the ninth inning of Boston's 8-1 Game 1 win against St. Louis. He gave up a leadoff home run to Matt Holliday, but struck out Matt Adams to end the game in what would be the last of his 584 appearances in the big leagues, including five in the postseason.

Dempster, an All-Star with the Cubs in 2008 when he went 17-6 with a 2.96 ERA, finished with a 132-133 career record with a 4.35 ERA. After reconstructive elbow surgery led him to transition to closing for the Cubs, he saved 85 games over a three-year span before making a triumphant comeback as a starter with Chicago. After getting over their initial surprise, Dempster said, teammates congratulated him on a great career.

"At least a long one," he joked. "I don't know how great it's been, but I capped it off with a really, really great moment."

Dempster signed a two-year, $26.5 million contract with the Red Sox after the 2012 season. He made 29 starts for the Sox last season, especially filling a need when Clay Buchholz was shut down for three months with shoulder bursitis, and finished the season with an 8-9 record and a 4.57 ERA. He forfeited the $13.25 million due him this season by informing the club he wasn't fulfilling the last year of his contract.

"The first thing I asked him was, 'You thought about this, right?'" Cherington said. "I wanted to make sure he spent a lot of time on it. He had. With anyone else, you might sort of wonder if they had processed it enough. Ryan, as soon as he said it, you kind of knew he put the time into it that he needed to make this decision, and I respect the decision he made."

Asked about leaving so much money on the table, Dempster said, "I've been really fortunate, extremely lucky, extremely humbled by the amount of money I have made that has provided for me and my family for years and years. The money was not that difficult a decision."

During his big league career, Dempster was paid more than $89 million, according to Baseballprospectus.com. He's not the first player to walk away from millions, Cherington said, but it's still an uncommon gesture.

"In a career full of earning respect and building respect, he's ending his time with the Red Sox in a way that only bolsters that, strengthens that feeling about him," Cherington said. "It was ultimately the right thing to do in his mind. That doesn't mean it was an easy thing to do, and I have great respect for him making the decision that way."

The Red Sox, Cherington said, expect to place Dempster on the restricted list, which would free a spot on the 40-man roster. The GM said he expects that to happen at some point this spring.

A native of British Columbia, Canada, Dempster turns 37 on May 3. The stress of pitching 2,387 regular-season innings and throwing nearly 40,000 regular-season pitches (39,635) has taken its toll. Dempster pitched through groin and neck issues last season; his neck, where he has a bone spur, remains especially problematic. He also cited a desire to spend more time with his three children.

"Talking to Ryan, even before he came down here today, there were mixed emotions on his part," Farrell said. "He's had a great career. You congratulate him on that, but I think when the end is nearing [and] ... the physical side of things take away from the performance, you empathize with that and know you can't go on and play this game forever."