"After a long offseason and thinking about things and seeing where I was at both physically and personally, I just made the decision that I'm not going to pitch in the 2014 season and go from there," Dempster said. "I had an incredible run, a chance to play 16 years in the Major Leagues and be around a lot of great teammates, made a lot of good friendships, a lot of great memories, you know, but I just feel that given where I'm at with my health, with how I feel personally, I just feel like it's in the best interest of both myself and the organization as a team to not play this year."
The announcement came the same day all Red Sox pitchers and catchers underwent physicals, and one day in advance of the team's first official workout of Spring Training.
"The past few years have been tougher and tougher as you get older going through different things," said Dempster. "There are some issues I have with my neck that have made it harder and harder to throw a baseball and throw it like I'm accustomed to throwing it. I could have had a choice of trying to spend the entire season trying to work through those and trying to be able to pitch.
"But I just felt like it's something that's preventing me from doing the job I want to do, and I'm not going to go out there and put my team at a disadvantage or me at a disadvantage by not being able to compete the way I'm able to compete."
By making the decision in the fashion he made it, Dempster gave up his guaranteed salary of $13.25 million.
"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," said Cherington. "In his mind it was the right thing to do; that doesn't mean it was an easy thing to do. We have great respect for him making the decision that way."
Though the 36-year-old Dempster spoke of his career almost in the past tense during his 16-minute news conference, even noting how his strikeout to end Game 1 of last year's World Series would be a nice way to go out, he left open the possibility of pitching again.
The Red Sox are likely to place him on the restricted list this season, meaning he isn't eligible to sign with another team until 2015.
In a sign of the respect Dempster has earned throughout the years, several of his teammates, including John Lackey, Mike Napoli, Jon Lester, Clay Buchholz, Dustin Pedroia and David Ross, all stood in the background as he addressed the media at an outdoor bench.
"I don't even want to look at them right now," said Dempster, knowing that his eyes would surely water if he did. "It's awesome, man. They're a huge support system for me, for each other. We were there for each other as much on the field as we were off the field. And in so many different ways. A lot of great memories, a lot of fun. Those memories are just going to continue. Like I said, I played 16 years in the big leagues and have never been around a team like that, so it's incredible."
On the field, Dempster was known as a fierce competitor, a two-time All-Star who gave everything he had as both a starter and a closer. But off the field, he was the master at keeping everybody loose.
There were team flights and clubhouse meetings when Dempster would have the entire team in stitches by doing voice impersonations of teammates.
"I wish some of you could have been privy to some of the stuff that happened off the field and in the clubhouse and on planes and buses and all that stuff," Cherington said. "He was a great pitcher, and I don't want to take away from that. But he also has great instinct for when the air needs to come out of the balloon on a team. He always picked the right moment to do it."
One of those moments was when Dempster informed Farrell of his decision.
"I joked with John a little bit after we talked about it," said Dempster. "I said, 'Sorry skip to throw this on you last minute, but you're going to have to find a new Opening Day starter.'"
In truth, Dempster was going to be in a fight to earn a spot in a loaded rotation that had six established starters vying for five spots.
Ever the realist, Dempster knows he might have been the odd man out by the end of camp. But he emphasized that had nothing to do with his decision.
"No, that didn't play a factor at all," Dempster said. "I love competing."
And the Red Sox were certainly on board with the righty fighting to keep his spot in the rotation.
"He knew that he was going to be coming into camp competing for a spot in the rotation," said Farrell. "You let things play out. We couldn't project, 'Would you go to the bullpen?' … We didn't go that far. It was, 'Hey, you're in competition for a spot in the [rotation].'"
Dempster, who turns 37 in May, was 8-9 with a 4.57 ERA in 32 games (29 starts) last season.
Dempster has gone 132-133 with 87 saves and posted a 4.35 career ERA in 579 games (351 starts) over 16 years for the Marlins, Reds, Cubs, Rangers and Red Sox.
Dempster came to Boston prior to the 2013 season and was credited as one of the many veterans who helped change the culture of a clubhouse which had lost its way the previous couple of years.
"It just stinks from a teammate's standpoint. We love that guy," said Ross. "He's such a good piece for us. He makes everybody around him better. You laugh a lot. He's good for the young guys. Every young guy can learn from Ryan Dempster. He's one of the best I've ever been around."
Clearly, there will be a spot in baseball for Dempster once he officially retires, be it in uniform, the front office or the broadcast booth.
"Sometimes you spend years around a player and never feel you get to know him, and sometimes it's a week and you feel you get to know him really well," Cherington said. "That was the case with Ryan. I felt, I think everyone felt, as soon as he walked in the door last winter and then in Spring Training, you just sort of felt like you knew him for a long time."
One of the most poignant moments in the hours after the Red Sox won the World Series last Oct. 30 was Dempster throwing batting practice on the Fenway field to several of his family members and friends.
Perhaps deep down, he knew then he would be stepping away. It certainly seems more likely than not that Dempster has thrown his last pitch in the Majors.
"I don't know yet. I'm just looking at the 2014 season to know that I won't be playing this year," Dempster said. "If something changes then obviously something changes. I don't see that changing anywhere in the future, but I also don't want to close the door on that. I'm just looking at it from this year going forward."
No matter what happens in the future, Dempster seemed completely at peace with the decision he announced on Sunday.
"At the end of the day, if this is the end, then this is the end, and what a great way to go out," Dempster said. "To sit there and think about the last batter I potentially could ever face in the big leagues was a strikeout to end Game 1 of the World Series, what better way to really write it? It's been an unbelievable time and I'm comfortable with this decision."