The 2007 World Series saw the Red Sox sweep the Rockies and served as the stage in which Ellsbury established himself, as a 24-year-old rookie who debuted in late June, ultimately replaced Coco Crisp in the starting lineup and batted .360 in his first postseason.
The 2013 World Series, which finished with a 6-1 Red Sox win over the Cardinals at Fenway Park in Game 6 on Wednesday night, leads right into the uncertain world of free agency.
"I haven't thought about that right now," Ellsbury said, with ski goggles covering his eyes and champagne bottles in each hand. "I'm just going to celebrate with my teammates and just enjoy the moment, you know?"
The moment probably doesn't happen without Ellsbury. He batted .344 (22-for-64), scored 14 runs, drove in six, notched five extra-base hits and walked seven times in these playoffs. In the Game 6 clincher, Ellsbury went 2-for-4, adding a double and scoring a run in each of Boston's three-run innings and somehow dodging a rundown.
"I mean, this is what it's all about," Ellsbury said. "You want to be on the big stage, you want to help the team. We treated this like a Game 7. You never know when your opportunity is going to come again, and we're so happy we closed out tonight.
"It's so rewarding this year. I feel very fortunate to raise the banner with this group of guys. It's been so much fun."
In five days, Ellsbury will be a free agent, and he'll be expensive. He's widely considered the second-best player available, behind Yankees second baseman Robinson Cano, and is coming off a bounce-back season that saw him bat .298/.355/.426 with a Major League-best 52 stolen bases. And -- this is never a small thing -- Ellsbury is represented by hard-line negotiator Scott Boras.
"I really haven't had a chance to look forward too much," Red Sox general manager Ben Cherington said of roster construction moving forward, "but we think we're in a good position."
Ellsbury is one of four notable pending free agents for Cherington, along with first baseman Mike Napoli, shortstop Stephen Drew and catcher Jarrod Saltalamacchia. And Boston may have a natural replacement for Ellsbury in 23-year-old center fielder Jackie Bradley.
But Ellsbury, taken with the 23rd overall selection in the 2005 First-Year Player Draft, has long been a cornerstone of the Red Sox's offense, compiling a .297/.350/.439 slash line, making an All-Star team and bringing Gold Glove-caliber defense to a premium position.
Starter Clay Buchholz came up from the Minors with Ellsbury six years ago, though he didn't crack the postseason roster in '07 -- and he'd like to see the Red Sox find a way to keep him.
"Ells is a really, really good player," Buchholz said. "That's probably an understatement, too. The dynamics of him doing what he can do on the field, there's not many players like that. I'd love for him to come back. I can give up rockets up the middle and he'll catch them."