When Steve Hilliard walked into Theo Epstein’s suite at the O’Hare International Airport Hilton in early November, it was setting up as little more than a Southern California reunion.

What it became was the foundation for what turned into Wednesday’s Fenway Park press conference introducing John Lackey as the newest Red Sox.

What happened in between?

“I had not experienced anything quite like that,” Hilliard said by phone following his client’s introduction.

Lackey had gotten to the Red Sox, which was big news. But how he got there was the surreal story the agent referred to, one that started with a handshake and wave of disbelief in that Chicago hotel room.

The two had become friendly years before while Epstein was a young executive with the Padres and Hilliard was working as a sports agent. The connection was a natural one considering both had made the trek west after growing up in Massachusetts, with Epstein attending Brookline High School and Hilliard, a Norwood native, attending Roxbury Latin.

Now the two were getting together during the General Managers Meetings under the guise of discussing one of Hilliard’s clients, John Lackey. Expectations from Epstein’s behalf, however, were that the most likely scenario was that the meeting would yield a bit of reminiscing and not much more.

The Jason Bay negotiations weren’t moving along, but it still was early in the process, and Scott Boras had yet to dig into his “Matt Holliday should get paid like Mark Teixeira” mantra.

And there was that lingering perception Epstein couldn’t shake — Lackey couldn’t have truly told his agent that he wanted to play for the Red Sox.

But he did, and it was Hilliard’s job to not only relay that message but make the Red Sox general manager truly believe it.

“[Epstein] looked at me in disbelief,” Hilliard said of the reaction when it was passed along that Lackey truly would want to play for the Sox. “It was like I told him something unimaginable.”

Epstein had admitted that the images of Lackey looking over his shoulder at Fenway’s left field wall, setting off a stream of demonstrative looks of discomfort and dissatisfaction, embedded doubts in regards to the pitcher’s interest. (Through 2007, Lackey’s record at Fenway was 1-5 with a 7.24 ERA in eight regular and postseason starts.)

And even after that first get-together in Chicago, the wall of doubt still existed.

Then, as Hilliard put it, the bricks started to fall.

The first came when the agent was walking out of his La Jolla, Calif., office while talking on the phone with Epstein. It was in that conversation that Hilliard informed the GM that Lackey’s wife, Krista, was from Sanford, Maine, and went to the University of New Hampshire.

“I could tell, even over the phone, that [Epstein] was making a mental note of that,” Hilliard remembered.

The second part of the equation was the fact that it was made clear that former Red Sox reliever Brendan Donnelly had offered a bit of recruitment on the Sox’ behalf without the team even knowing. Donnelly, who played in Boston in 2007, was extremely tight with Lackey and had relayed enough positives that the memories of those rough times at Fenway were made a bit more inconsequential.

And then there was the reminder regarding Lackey’s persona. Sure, he was emotional during those failures at Fenway, but that was because he wanted to win, and in the pitcher’s mind there were few places he would be more able to be competitive over the life of his new contract than Boston.

Piecing it all together, Hilliard sensed a gradual change in how Epstein was viewing Lackey’s interest.

“By the time we got to Indy I could tell [Epstein] was serious about it,” the agent said.

By the time the Winter Meetings started — more than a month after that initial conversation in Chicago — the Red Sox hadn’t gotten the vibe that the Bay talks were going in a forward direction, and Boras wasn’t backing off the Teixeira/Holliday comparisons.

So when Hilliard walked out of the Red Sox’ suite at the Winter Meetings in Indianapolis, in which he had — by himself — met up with Sox pitching coach John Farrell, manager Terry Francona, assistant general manager Ben Cherington and Epstein, his thoughts had changed from wondering if the team’s GM would believe his client’s interest to “this could happen.”

The calls increased, and so did the negotiations. The Red Sox still were only offering four years, which (as in Bay’s situation) wasn’t going to get the deal done. Finally, at the outset of last weekend, the team decided it was time to move on from the outfielders and prioritize the pitcher.

Five years, $82.5 million was put on the table.

It was almost identical to the deal signed by A.J. Burnett with the Yankees the year before. Hilliard would argue that Lackey perhaps deserved more. The Red Sox were thinking perhaps slightly less. But there was no getting around it for both sides that this was probably an unavoidable comparison.

Throughout Saturday Hilliard tried to reach Lackey with the news, but he could only talk to his wife as the pitcher was in the midst of working out at a gym near his Southern California home. The message that the Boston Red Sox wanted Lackey to play for them would have to be passed on by the woman from Maine who went to college in New Hampshire. Needless to say, it wasn’t long before the agreement was reached.

A deal that surprised many — including the Red Sox — was done, and a team had officially set its course for the 2010 season.

“It took a while. [Epstein] was so skeptical,” Hilliard said. “But it all worked out.”