Epstein finally found that opportunity on Wednesday, dealing the speedy center fielder to the Royals for reliever Ramon Ramirez.
Ramirez, a 27-year-old righty, went 3-2 with a 2.64 ERA in 71 games in 2008. He registered 70 strikeouts in 71 2/3 innings.
"In Ramirez, we believe we've acquired a young, controllable reliever that can really help our bullpen," said Epstein. "He has a plus fastball, 92-95 mph, and an outstanding power changeup. A lot of people think it's a split, [but] it's actually a changeup, 87-88 [mph], that's a swing-and-a-miss pitch for him against left-handed and right-handed hitters. And [he has] a pretty good slider to go with it.
"He's very quietly had a tremendous amount of success in the Major Leagues over the last two and a half seasons. He pitched effectively, very effectively, for the Royals in the eighth inning last year. We were looking for an upgrade in depth to add to our bullpen."
Ramirez, reached by MLB.com via phone from the Dominican Republic, sounded excited about the next challenge in his career.
"I feel fine about it because I realize baseball is a business and every team tries to do the best for their organization," Ramirez said through an interpreter. "If I'm going to Boston, I'm going happily and I will work as hard as I worked for Kansas City."
How does Ramirez fit in to manager Terry Francona's bullpen? He figures to join Hideki Okajima and Manny Delcarmen as key setup relievers for Jonathan Papelbon. His addition also gives the Red Sox added flexibility with Justin Masterson, who was a star setup man down the stretch but also has the ability to start.
"Ramirez, he pitched the eighth inning and dominated last year for Kansas City," said Epstein. "He may not have to pitch quite that deep in games for us. He does give us the flexibility to start Masterson if that's ultimately what we end up feeling is in the best interest of the ballclub.
"Both Masterson and Ramirez dominate right-handed hitters, so in that way, Ramirez could potentially replace Masterson in the 'pen. But Justin, as we said at the end of the year, he gives us great flexibility. If we need him to start, that's what he'll do. If we need him in the 'pen, that's what he'll do. We think he'll be effective in both roles. It's not easy to find a controllable reliever with a good track record and plus stuff. We felt like whether we keep Masterson in the 'pen or not, adding Ramon can only make us better."
Because Jacoby Ellsbury is viewed as Boston's center fielder of the present and future, Crisp was deemed to be expendable.
But with Crisp's value as a defender and a baserunner, Epstein chose to hang on to him in 2008. It paid off, as several injuries to other members of the Red Sox -- not to mention some inconsistency by Ellsbury offensively -- enabled Crisp to have 361 at-bats.
The switch-hitter batted .283 with seven homers and 41 RBIs, stealing 20 bases.
"Coco is a good player," said Epstein. "We want to take a second to just thank him for his efforts while he was with the Red Sox for three seasons. He played through injuries while he was with us, he played hard. He was a big part in us winning a world championship. His efforts here were certainly appreciated. He did it with a lot of class along the way."
Crisp's most memorable at-bat during his time with the Red Sox came in Game 5 of the 2008 American League Championship Series against the Tampa Bay Rays. On the 10th pitch of his at-bat in the bottom of the eighth inning, Crisp rifled a game-tying single to right field, bringing Boston all the way back from a 7-0 deficit.
Crisp was excited about the trade to Kansas City.
"I know my agent had told me there was a possible trade in the works within this week, and all that waiting and anticipating to see if it even happens kind of keeps you on edge," said Crisp, who was in California and found out about the deal at 7 a.m. PT. "When I finally got the news that I was going to Kansas City, it was exciting."
The Red Sox went on to win the game to stave off elimination and also won Game 6 before bowing out with a 3-1 loss in Game 7.
Crisp was brought to Boston via a trade from the Indians in January 2006. The hope was that he could replace Johnny Damon in both center field and the leadoff spot.
"It was a learning experience, definitely," Crisp said of his time in Boston. "I had a lot of fun. It's been a great experience for me coming from a contending team like Cleveland to a team that was already in the mix playoff-wise. I've learned on the field and off the field. It's helped me grow.
"The one negative aspect that came out of the whole thing was that I was plagued by nagging injuries, primarily the whole time I was there, with the exception of a month here or a month there and toward the end of this season, when I was fully healed from my hand injury, which I hurt within the first five games of coming over to Boston. It was an up-and-down ride. Most of the time, I enjoyed myself over there, even though it was difficult."
But Crisp's time with the Red Sox got off to an ominous start, as he fractured his left index finger in the fifth game of the season. Though he returned six weeks later, Crisp struggled offensively for much of 2006 (.264 average) and '07 (.268).
As it turned out, Crisp hit mainly toward the bottom of the order during his three years with the Sox. Crisp is an aggressive hitter and Boston likes to have a more patient approach from the leadoff spot.
"His career with the Red Sox didn't get off to the start that he wanted," said Epstein. "He was playing pretty well early in the '06 season and ended up breaking his finger. When he came back, his offense never rebounded all the way to his previous norms but he turned himself into, especially in 2007, a tremendous defensive center fielder. He helped us win a lot of games with defense in 2007, the year we ended up winning the World Series."
Crisp had a strong finish to 2008, hitting .375 in September.
Ellsbury batted .280 in 2008, his first full season, belting nine homers, driving in 47 runs and scoring 98 times.
"I think Jacoby had a very solid rookie season," said Epstein. "I know expectations were probably unreasonably high for him, given the numbers he put up in a really small sample in 2007 and during the postseason, but this was a more than acceptable rookie year, and the one thing we like about young players, especially young players who work hard like Jacoby does, is they get better."
The same can be said of Ramirez.
"Of course, it's a big motivation to go to a team like Boston, but don't forget, with every team -- no matter how good or bad they are -- you have to prove yourself and you have to contribute to the team," Ramirez said.
Over three seasons, Ramirez has pitched in 154 games, all in relief, posting a 3.62 ERA.
"We have excellent reports on his makeup," said Epstein. "I've talked to a number of sources close to the clubhouse there and he's the first one to the ballpark. He's an extremely hard, diligent worker. He's tough, fearless and the manner in which he pitches reflects that. We don't expect he'll have any difficulty adjusting to a bigger market. Coming to Boston, he's a pretty tough, pretty fearless kid and he won't be fazed."
Epstein will now be on the prowl for a fourth outfielder to complement the starting trio of Jason Bay, Ellsbury and J.D. Drew.
"We'll cast a wide net and certainly look outside the organization," Epstein said. "I think what would make sense for us at this point is a right-handed-hitting fourth outfielder that could protect us in center and play against some left-handed pitching. We have a lot of different options, a lot of different places we can turn to fill that role. We have some talented outfielders on the way up. Most of them are left-handed. I think a right-handed hitter would be a more appropriate choice to fill this role."
Ian Browne is a reporter for MLB.com. Dick Kaegel, a reporter for MLB.com, contributed to this report from Kansas City. This story was not subject to the approval of Major League Baseball or its clubs.