Why a camo hat was key to the Cubs landing Jon Lester

Jeff Passan
·MLB columnist

SAN DIEGO – The package arrived with a Chicago postmark. Throughout the process of his courtship, Jon Lester received plenty of nice gestures from those interested in signing him – the case of Opus One from one team should go down well – but this was different. Inside the box were a camouflage-colored hat and T-shirt with the sort of logo that looks slightly out of place on such gear: the Chicago Cubs'.

Nothing can explain Jon Lester's decision to leave behind his time in Boston and more money in San Francisco for the shores of Lake Michigan quite as well as the cheap swag that greeted him in the mail a few weeks ago. It represented everything that mattered to him, which happened to be the same thing that has buoyed the Cubs through a tenuous rebuilding process: trust.

In club president Theo Epstein, right, and general manager Jed Hoyer, Jon Lester found trust. (AP)
In club president Theo Epstein, right, and general manager Jed Hoyer, Jon Lester found trust. (AP)

No matter how many times the Red Sox apologized for screwing up by lowballing him, and no matter how much effort the Giants put in to convincing Lester he was the vital piece to their next championship, nobody could match the trust forged by Theo Epstein and Jed Hoyer, architects of the teams that won Lester a pair of World Series rings in Boston.

This wasn't rigged, not by any means, not with Lester waiting for Boston to woo him or the New York Yankees to step in and try or the Atlanta Braves to give him reason to stay at home. But from their first meeting to the final phone call Tuesday night, the Cubs wielded the two most formidable weapons that trumped even dollar signs.

Epstein and Hoyer, the Cubs' president and general manager, knew Lester well enough to know how much he'd dig the camo gear. Every few days, they checked in with him in one fashion or another, respectful enough to avoid sounding desperate, desperate enough to forge a greater level of respect. They saw him as an 18-year-old kid who didn't make it out of the first inning of his first pro start and as a 22-year-old man who beat cancer and, now, as a 30-year-old husband and father who desired something more, something genuine.

So, yes, the organization that as much as any asked those who love it to trust the plan now needed to pull off its most convincing act yet with a man it ultimately would pay $155 million to throw a baseball for the next six seasons. The reinvention of the Cubs didn't necessarily depend on this, but after losing the Russell Martin sweepstakes to Toronto, Lester represented something more than the typical free agent to Chicago. He was proof that this plan wasn't some tunnel with a light that kept going out.

[ Related: Jon Lester responds to congratulations, criticism on Twitter]

Since Epstein and Hoyer took over the Cubs in 2011, they've spent almost every day in asset-accumulation mode. They took a sledgehammer to the mess they inherited and were more focused on getting young than patients at a Botox clinic. As energizing as it was – as invigorating as a clean slate can be for those who relish in building something – the losing gnaws at patience, makes even the most steadfast question where, exactly, this thing is going.

The answer was: here, at the Manchester Grand Hyatt, deep into negotiating sessions that sucked $20 million more out of the Cubs than their initial offer and made Lester the second-highest-paid pitcher on an annual basis. It wasn't the most money – while they denied it publicly, the Giants, according to numerous people involved, expressed a willingness to go as high as $168 million – but the combination of money, comfort, trust and possibilities.

"It reminds me a lot of the 2003-04 Red Sox," Lester said in early December. "John Henry buys the team and they transform Fenway. A lot of that stuff is very compelling to me."

[ Related: Cubs won the lottery with Lester; now they must win games]

The Cubs are overhauling Wrigley Field, turning it from a 20th-century relic into a 21st-century stadium worthy of excitement. They're playing the patient game, not trying to turn the Lester signing into a tidal wave of expectations but a nice, surfable swell. Any thought of going in hard for 2015 is silly, particularly with the youth they plan on scattering across the field at nearly every position. This is a team that's built to win in 2016 and '17 and '18 and beyond, not this year. They didn't get where they are today by sacrificing for the short-term.

They did it through the sort of creativity that helped them land Lester. No, a ball cap and shirt weren't going to sway Lester one way or another. They simply reminded him that Epstein and Hoyer know him, know what appeals to him, what makes him tick. Beyond what he'll do on the mound, Lester sets an almost unparalleled example of intensity before, during and after his starts. It's a culture thing, unquantifiable, immeasurable, still very real. If the $155 million pitcher is the hardest worker on the team – and Lester will be – the kids making $500,000 haven't an excuse in the world to skirt doing the same.

It was a perfect match, really, a right-pitcher-for-the-right-time bit of kismet. And Tuesday night, when Epstein and Lester finally got on the phone together, it was obvious to the few in the Cubs' suite just how much it meant. This wasn't the first step toward winning a World Series for the first time since 1908, and it won't be the last, but it was one of those seminal moments that puts the Cubs in a far greater place than they were before.

Inside the room, the energy was palpable. The tunnel was shortening, the light a gleaming trophy, which is far off but not as far as it was. On the night the Cubs shot back to relevance, they passed the phone around, told Jon Lester how excited they were to have him, hung up, celebrated until 4:30 in the morning and got back to work soon thereafter, plenty of it left to prove Lester's trust was as well placed as he hopes.

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