All the contenders were offering more money than Lester could spend in 100 lifetimes.
But the Red Sox could also sell him on a familiar landscape with teammates he's already friends with and a fan base that has adored him his entire career. The Giants had the best organization in baseball, three titles in the last five years and perhaps the best batterymate a lefty could ask for, Buster Posey, who went to Lester's home to recruit him in person.
They had a ballpark renovation, a well-respected manager and a 107-year-old World Series title drought with the veiled promise of immortality to the lucky ones who ended it.
"It was driven home that the organization hasn't won in a century, and he could be part of something historic, something unique and something extraordinary," agent Seth Levinson said.
The Cubs' full-scale press was relatively low-key, unless you consider sending Lester some camo Cubs caps a hard sell. There was the usual stuff — bottle of wine and flowers for his wife, Farrah.
"You know they're kind of thinking of you," Lester said. "It was cool."
President Theo Epstein said he would have soaked himself in deer urine and gone hunting with Lester if that's what it took, which Lester later suggested was TMI and unnecessary.
New manager Joe Maddon called Lester, but didn't make a trip. The talk was enough. Lester said he respected how Maddon "looks at the game in a different light," and what he means to the rebuild.
"When you make a statement like bringing in a Joe Maddon, that just adds to the decision-making," Lester said. "Makes it that much more interesting."
The Cubs brought Lester to Wrigley when the bleachers looked like they had been bombed, and just in time for a mini polar vortex. They gave him a scouting report on the media, telling him it was less antagonistic than Boston. Chairman Tom Ricketts took him to a downtown steakhouse and bonded over a love of hunting.
Lester heard from Ryan Dempster , Jeff Samardzija and Jason Hammel on how cool it was to play at Wrigley, and to live in Chicago. All three had been traded by Epstein during the Cubs' rebuild but understood it was part of the plan to restock the system, and left on good terms.
"Are these guys close?" Lester asked Samardzija. "Are they there?"
Dempster was a key in relating how he and his family would enjoy the city, Lester acknowledged.
Assuredly Dempster also told Lester he automatically would be inducted into the "Stanley's Mafia," a diverse group of celebrities with Chicago ties — including Dempster, Chris Chelios, Kerry Wood, Eddie Vedder and John Cusack — who sometimes congregate at Stanley's Kitchen and Tap. Wood let Lester know he would be "honored" knowing Lester would wear his number, which Lester also said was a tribute to Nolan Ryan and Walter Payton.
"Obviously I wouldn't be here right now if they didn't speak highly of Chicago," he said.
Still, Lester was undecided heading into the winter meetings in San Diego.
The information overdose was on full display in the days and hours leading up to the decision, with a hail of tweets coming from all directions. A personal visit from Red Sox owner John Henry "moved the needle" toward Boston said one tweet, and then another declared Boston was out of the picture and it was down to the Cubs and Giants. Then came a tweet that Lester was "leaning toward the Giants," followed almost immediately by a quote from Giants assistant GM Bobby Evans saying they "did not receive a rose," a modern-day metaphor for rejection.
The tension was building in San Diego, where executives of the Cubs and Red Sox were following the bread crumbs of "information" on Twitter and doing their own polling to see where Lester stood.
"It was therapeutic not to read it, since I'd say 75-80 percent of what was written was inaccurate, wrong or miscaracterization," Levinson said. "And it really didn't help the process. It just added a lot more stress and made everybody put forth a greater effort to get it right from our end."
Everyone expected a decision by Dec. 9. As that night wore on with no word, Levinson texted Lester: "Where the hell are you? Could you please call me?"
Meanwhile, Epstein and general manager Jed Hoyer were huddled outside a restaurant making calls in the most remote place they could find when a disheveled Chicago reporter walked past with carryout food. After first mistaking the reporter as homeless, they waved, then waited for him to pass before continuing the call.
Around midnight in Chicago, a tweet by foxsports.com's Ken Rosenthal announced the Cub were the winners. Lester said he and Farrah didn't make the final decision until a few hours before the announcement.
"By the time it was released, at best, he made the decision an hour and a half earlier," Levinson said.
The Cubs had laid out their game plan for 2015 and '16 and spoke bluntly, Levinson said. The soft-sell approach turned out to be the right one. After three years here, the Cubs' brass understand we don't really need to sell anyone on the coolness of Chicago.
"Spectacular," Levinson said of the Cubs' plan. "They were relentless, they were detail-oriented, and as important as anything else, they were sincere. They were completely transparent and brutally honest with all the information we required."
Lester finished his briefing by saying he doesn't believe in curses, asking "what if (Moises) Alou jumped up and (the ball) hit off the heel of his glove" on that infamous October night in 2003.
"Of course, it ruins that guy's life and they blame it on a curse," he said.
Lester does, of course, know all about the Billy Goat curse.
"Absolutely," he said. "We'll do what we need to do. If we need to bring some goats around, we'll do that."