So Lackey was going to want to come to the Red Sox in his free-agent year? General manager Theo Epstein, who formally announced the signing of the righty to a five-year, $82.5 million contract on Wednesday, didn't see this one coming when the offseason started.
"Watching him from across the field, we've always seen him as a big-game pitcher, a top-of-the-rotation guy, and a really tough competitor, but we never really thought he'd be interested in Boston," Epstein said. "I guess it's one of those things -- when you play across the field from someone you just kind of see them as the opposition and that's it."
In this case, however, that wasn't it.
"I was always interested in coming here," Lackey said. "Winning was definitely my first priority of a team to go to. With this franchise and their history and the way I've seen from the other side of the field, I've been knocked out of the playoffs a few times by them, I know I'm going to have a chance to win here and that means a lot."
It was at the General Managers' Meetings in Chicago back in November when the Red Sox first realized Lackey could be an option.
"When I talked to Theo at the GM Meetings in Chicago and told him John had interest in coming to Boston, he really didn't believe me," said Steve Hilliard, Lackey's agent. "You could just tell by the look on his face that he really didn't believe me. But over time, we had subsequent conversations and at some point he started to actually believe that was true. Initially, he looked at me like, 'Are you kidding me? There's no way that John would be interested in coming here.' Not after some of the things over the years, the rivalry and maybe some of the comments that had been made along the way. It took some convincing. At the beginning, Theo was kind of skeptical."
And even when Epstein's skepticism started to go away, Lackey was no sure thing. You see, the Red Sox were on parallel tracks. Either they would make a high-priced investment for the offense -- such as retaining Jason Bay or signing Matt Holliday -- or they could go all in on Lackey.
By the end of the Winter Meetings, it became increasingly apparent that Bay and the Red Sox would not find common ground. Epstein then ratcheted up his intensity on Lackey and by Monday, a deal was basically done. All that was left was the physical and finalizing the contract language.
Lackey, who had several other teams in pursuit, did find Boston to be plenty intriguing. And now, he will join Jon Lester and Josh Beckett and try to help the Red Sox get back to the World Series.
In nine career starts at Fenway, Lackey is 2-5 with a 5.75 ERA.
"A lot of that had to do with going against a great team and now being a part of it, I'm excited about that," Lackey said. "If you look at the last couple of years, I've done pretty well here. I'm excited about the opportunity and just really fired up to be a part of this organization."
While the Red Sox had always had the upper hand against Lackey, things started to change dramatically on July 29, 2008. At his former house of horrors, Lackey had a no-hitter at Fenway with one out in the ninth before Dustin Pedroia broke it up.
Though Lackey lost his only game at Fenway in 2009, he pitched well, giving up two earned runs over 7 2/3 innings. And backed by Lackey's sparkling outing against the Red Sox at Anaheim in Game 1 of the 2009 American League Division Series, the Angels swept that series. The last time Lackey had been at Fenway before this week, he was doused in champagne after his Angels had made that dramatic ninth-inning comeback against Jonathan Papelbon in series-clinching Game 3.
But things can change quickly in baseball, and Lackey hopes his next champagne celebration will be in the home clubhouse at Fenway.
"There's been a lot of emotion both ways in regards to this team," Lackey said. "You get knocked out of the playoffs, there's not much worse than that, then I've thrown a couple of pretty good games here and finally we got it done last year but it's more just the respect factor. When you compete against a team that many times, you see what they're about, and it will be a good fit for me, I think."
Ian Browne is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.