Damon has very much been front and center since arriving with the Red Sox in 2002. He has been on-base machine and a grinder for his team while always being accessible to the fans and media.
But like some of his teammates he's battled with the last few years, Damon wondered if the theme of the 2006 season in Boston would be one of changing Sox.
Mike Timlin, the stalwart reliever who carried the bullpen for most of the season, is also a free agent. So is Bill Mueller, the blue collar third baseman of the last three seasons. First baseman Kevin Millar, who helped change the culture of the clubhouse upon his arrival in 2003, might also be gone as a free agent.
And ever since July, there has been plenty of speculation that the club might explore a trade for superstar slugger Manny Ramirez, who has filled the cleanup hole at Fenway for the majority of his five seasons in Boston. Ramirez, with 10 years of service in the Major Leagues and five with the Red Sox, has the right to veto any trade.
In the span of an instant on Friday evening, the Red Sox went from defending World Series champions to a unit that could see its share of transition.
"This whole clubhouse could be different," said Damon. "I don't even know where to start. Mike Timlin is a free agent; Billy Mueller, who is going to look very attractive to many teams; Kevin Millar, who has been great in the clubhouse and has helped keep us loose. The Manny situation, what's going to happen with that? There's a lot of uncertainty right now. Of course, we wish we didn't have to start answering these questions, but, unfortunately, our season is over."
This is the type of transition any team goes through at the end of the season. But it was close to the heartstrings of these Red Sox, who suffered a gut wrenching defeat in the American League Championship Series two years ago, came back to win the World Series in the most dramatic fashion last year, and then willed their way to postseason play this year despite a barrage of injuries to key cogs.
The end -- getting swept out of the Division Series by the White Sox -- was all so sudden.
"I keep saying that it's still difficult to get over that we lost and we're not playing tomorrow," said Mueller. "I don't know what's going to happen in that regard with anybody or everybody. That kind of emotion I think will be something that will happen later if things end up that way. I would hate to think that at first, right now, because I just don't know. I would prefer to think positively."
There is a good collection of talent slated to come back, including captain Jason Varitek, designated hitter David Ortiz, right fielder Trot Nixon, shortstop Edgar Renteria, and the entire starting rotation, topped by a hopefully rejuvenated Curt Schilling.
"It's the nature of the business, unfortunately it has to happen that way," said veteran knuckleballer Tim Wakefield. "It's going to be sad, but it happens. Whoever is not here next year, I'm sure they'll do fine wherever they are."
The Damon negotiations are the ones that will be followed the closest.
"I think I'm the big guy they need to try to sign," said Damon. "I know the players are pushing for me to come back. [We'll] just have to see. I'm looking for five-plus [years]. We know what Manny and David can do, but I make them look good. And they make me look good."
The Red Sox, with the savvy Epstein running the front office and the ownership always committed to making a strong financial commitment, are all but certain to report to Fort Myers, Fla., in February with a solid team. It's just a matter of exactly what it looks like.
"If I get a chance, we'll reach out and see if we can sign back here," Timlin said. "I enjoyed it here. I had a great time. As is the business of baseball, there's free agents, there's turnover, guys move. They may bring in guys to replace the free agents that have better seasons and they could run back to the World Series next year. You never know."