Ryan Dempster showed off his Boston Red Sox bling, the World Series ring made with 14-karat white gold, 126 diamonds and 25 custom-cut sapphires and rubies.
It's hard to picture Dempster leaving the game on a higher note, but he wouldn’t rule out the idea of playing in 2015 after giving up $13.25 million and sitting out this season. Working as an MLB Network analyst doesn’t necessarily mean he’s closing the door on pitching again.
"I just need something to do this year,” Dempster said Wednesday during Wrigley Field’s 100th anniversary celebration. “For right now, I just think this is the best thing for me to do – take some time off and kind of look where I’m at. I’ll re-evaluate that down the road."
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Dempster made national headlines in mid-February when he reported to the Red Sox complex in Fort Myers, Fla., and announced that he wanted to spend more time with his family and treat the neck problems and physical issues that have been bothering him.
"The biggest thing is I haven't missed it like I thought I would," Dempster said. "I’m enjoying my time right now. It is harder, the farther you get away from it, to be able to get back into it. But I’m really, really comfortable and happy with my decision now.”
Dempster will turn 37 on May 3. He already made roughly $89 million during his playing career. He’s looking forward to a golf trip to Scotland with his family and enjoying another Chicago summer.
Dempster went 8-9 with a 4.57 ERA for the Red Sox last season. He once solidified the Cubs rotation, accounting for at least 200 innings every season between 2008 and 2011. He also notched 87 saves in a Cubs uniform.
What if team president Theo Epstein needs another pitcher next season, a veteran presence for the cramped clubhouse?
"We'll see what happens," Dempster said.
Dempster didn’t necessarily want to leave in the summer of 2012, using the hammer of no-trade rights and hanging out inside the team’s new Clark Street headquarters in the final hours leading up to the July 31 deadline. He looked up and noticed the MLB Network countdown clock when the Cubs finally completed a deal with the Texas Rangers: 4 minutes and 53 seconds.
Dempster recently watched a game from the Wrigley Field bleachers. He remembered making his first big-league start here on June 1, 1998 with the Florida Marlins (and getting knocked out in the second inning of a 10-2 loss).
“It’s an incredibly special place for me,” Dempster said. “I remember as a visiting player going to warm up, running out towards center field and having the right-field bleachers absolutely just rain down on me with insults, letting me know how bad I was going to do that day.
“They were definitely right.”
After recovering from Tommy John surgery and rebooting his career, Dempster became a huge part of the teams that won division titles in 2007 and 2008, but didn’t win a playoff game. One of his favorite Wrigley Field moments became the time the Blackhawks brought out the Stanley Cup for a White Sox game in 2010.
"I'll still never forget Jonathan Toews and Brian Campbell out on the mound," Dempster said. "They gave me the Stanley Cup and said: 'Here, pick it up.' I knew the rules and said I'm not picking this up. They said: 'If you don’t pick it up, 40,000 people are going to boo you right now.'
"I picked it up and what should have felt heavy felt as light as a feather."