The Arm (15 page)

“We were exceptionally honest about where we are in the life cycle,” Hoyer said later. “We told him that we're going to be very young. We didn't try to sugarcoat it or say we weren't. . . .
You're going to have to live through some growing pains with some young hitters, but that what we're growing has a chance to be pretty special.”

The day ended at chic RPM Steak, where Ricketts met the group in a private room and immediately bonded with Lester over their mutual love of hunting. Throughout the day, Epstein and Hoyer had noticed a different Lester than the one they knew in Boston, one more mature and comfortable with himself. He opened up, knocked off one-liners. Their dream pitcher was even better than they remembered.

Following dinner, Epstein, Hoyer, and the Levinsons hung around to talk business. Epstein's plan: get the Levinsons drunk and figure out what they really wanted. Tequila shots and beer flowed. Though the Levinsons never cracked, Epstein and Hoyer got the sense that $150 million would win them Lester. And so they felt confident about the initial offer they planned to present: six years, $135 million—nearly twice as much as the Boston offer that made this day possible.

O
NE WEEK AFTER THE MEETING,
Epstein and Hoyer sent another package to Lester. Inside was a camouflage hat featuring the Cubs' logo and a letter that showed just how unconventional they were willing to play in order to convince Lester to come to Chicago: even though the Levinsons hadn't yet responded to their initial offer, the Cubs told Lester they planned to increase it anyway.

“This is a bit of an unusual negotiating strategy, but we don't believe in playing games or stringing things along when we know what we want,” the letter said. “You are our absolute top priority and we don't want to leave anything back.”

The Cubs didn't know their first offer was still the highest. Detroit committed to five years and $100 million on the nose. While Toronto offered the highest annual salary at $25 million a year, it refused to go beyond five seasons. Atlanta, with whom
Lester met, indicated it would max out at six years, $120 million. Each was a respectable offer. Just not enough for where the market was going.

“We knew 135 wasn't going to get it done,” Epstein said. “I thought 150 was our walk-away. So we did go back and forth a lot on, ‘We want to make a move, we don't want it to be too big because we need to leave some room, but we don't want it to be too small and piss him off.'”

The goal: dazzle Lester enough that he would sign before the Winter Meetings, preventing another team from making a Godfather offer higher than the comfort zone the Cubs had already stretched. The day before Thanksgiving, the Levinsons set up a phone call with Lester, Epstein, and Hoyer during which the Cubs asked how interested he would be in signing now. The ploy failed. Lester asked for space instead.

Within twenty-four hours, the Cubs' fears were substantiated. Los Angeles Dodgers president Andrew Friedman called the Levinsons on Thanksgiving Day and said his team loved Lester but needed time to figure out how serious it could get. The San Francisco Giants, World Series champions three times in the previous five seasons, suffered from no such equivocation. They wanted in. Lester picked the brain of friend and 2013 Red Sox teammate Jake Peavy, now a Giant, about San Francisco's merits. Madison Bumgarner, the World Series hero in 2014, raved about the organization, the fans, everything. When star catcher Buster Posey showed up at Lester's house along with GM Brian Sabean and manager Bruce Bochy on December 1, the Cubs–Red Sox duel looked like it would have company.

“We have a new team to consider,” Lester told me, and excitement tinged his voice even as the process wore on him. At the ugly-Christmas-sweater party he and Farrah hosted—Lester wore a cardigan wired with blinking lights—friends tiptoed around the question of where he'd end up because they understood the stress. It wasn't just the text messages from reporters chasing completely
incorrect rumors thrown out on Twitter by a teenage kid. It was the idea that within a week, he would choose where he spent the next six years of his life, a hard enough decision for anyone, regardless of the money. And the knowledge that when he did sign the contract, he no longer would be Jon Lester. He would be $150 Million Man Jon Lester, his contract permanently attached to his name.

The Giants' interest spooked the Red Sox and Cubs into their own maneuvering. On December 5, John Henry and his wife, Linda, flew a private jet to Atlanta to meet with the Lesters. They brought two bags filled with presents for the boys and a case of Opus One wine, about which Henry raved. The get-together lasted an hour, of which fifteen minutes was devoted to talking business. Henry intimated three times that the Red Sox probably wouldn't be the highest bidder.

The Cubs, already the highest, finally made that second offer the same day: six years, $150 million, with another $250,000 a year to cover personal jet service to ferry Farrah and the boys to and from Atlanta. The family travel bonus was symbolic; they knew Lester wanted to be wanted. Epstein wrote one final letter to Lester the next day. With the Red Sox sending in Henry to close their deal, the Giants priming their own huge offer, and the Dodgers seemingly lurking, Epstein couldn't stop typing on his iPad. This would be his last message to Lester before the Winter Meetings started, and he wanted it to be memorable.

Going to Chicago has “been a wonderful rebirth for all of us, one of the best decisions we've ever made,” Epstein wrote. Chicago offered Lester the same opportunity: to become part of something novel, this idea that he, his old bosses, and a bunch of kids could slay a century of disappointment. Of all the appeals to his psyche, this one resonated the most with Lester, who said every time we spoke: “It would be pretty cool to win there.” This challenge was Epstein's best bait, stronger than Boston's familiarity and San Francisco's rings.

“If you do decide to join us in Chicago,” the last sentence of Epstein's message read, “we look forward to taking care of your family, to great fun to be had together, and to the biggest celebration in the history of sports!”

W
HEN JON LESTER NEEDS PEACE,
he takes Interstate 85 south into Meriwether County and goes hunting. On December 8, he drove to his farm with a Mathews bow, a stand that locks onto a tree, and the promise of silence. He needed all of it to help him with the biggest choice of his life.

“As soon as you make the decision and you're up there in the press conference, you're always gonna kind of second-guess it,” Lester said. “You're human. You're going to ask if you made the right decision. And you'll never know until you play the whole thing out.”

He returned from his hunting trip without an answer, so he and Farrah compiled a two-sided list, a technique his father taught him. On one side were the pros, on the other the cons. He compared and contrasted to figure out what was truly important, to avoid emotional intervention, to force a choice. And if he could rationalize living with the cons of that decision, he would stick with it, knowing that nothing is perfect.

Boston was home, a place with his best friends in baseball, the team with which he won two World Series—familiar, comfortable, easy. It was also unwilling to pay what the market thought he was worth, and no matter how many times the Red Sox apologized, the pain of his departure never flagged. San Francisco was the minidynasty, its ballpark built for him to throw two hundred strong innings, the city a jewel, and it threw a late trump card: if Lester committed to the Giants, the team indicated a willingness to give him a seventh year and a deal in the neighborhood of $168 million. San Francisco was also a five-and-a-half-hour flight from Atlanta, twice as long as the other two cities, and the prospect of
hauling Hudson and Walker across the country bothered him. If it were about the money, he'd have gone to San Francisco.

It didn't feel right. Chicago was exciting, a new beginning, with intimations of immortality, with big money and two men he trusted who were promising him the world. On the other side of the ledger was the potential for a bust with a group of kids he'd never met.

“When it came down to it, it's still Red Sox and Cubs,” Lester told me. “It's like your first love. No matter what happens, you always kind of go back to that person. You fall back on that. Regardless of what the money and years were, it always came back to Boston for the comfort, knowing where spring training is, knowing the guys in the clubhouse, the training staff. All that stuff. And then you have to sit there and ask whether you're really going to choose the unknown—this new city, this new place, that's never won.”

First he needed to hear from Boston. Out of respect, he gave the Red Sox last right of refusal because, unlike the Cubs, Boston hadn't budged from what it handed Lester in the envelope nearly a month earlier. Chicago bumped its offer a third time, to the $155 million that caused the fight between Epstein and Sam Levinson, plus a seventh-year option—another $15 million that would vest if Lester pitched two hundred innings in 2020 or four hundred between 2019 and 2020. The Red Sox's final offer matched the Cubs' initial one: six years, $135 million. Boston knew it was $20 million short. It did not matter. This was the Red Sox's number. It would not move.

Lester had made history in Boston, winning the final game of the 2007 World Series. Now he planned on making more in Chicago. It was over. Just like that. The conflict, the agita, the indecision, all gone in a clink of champagne glasses with Farrah.

“The biggest thing that made me believe in the Cubs was Jed and Theo,” Lester said. “They made me believe in what they believe in.”

He and Farrah gathered the boys and headed to dinner at Chops, a steakhouse near their home, where the manager, a Yankees fan who a few months earlier bet Lester a dollar he would sign with New York, asked, “Are we here to celebrate or are we here for dinner?” Lester's answer was to order a $400 bottle of wine.

The calls to his agents and the Cubs prompted a raucous scene in the Levinsons' suite, where Epstein, Hoyer, and Maddon, all there for the Winter Meetings, gathered to celebrate—minus the Jäger. Telling other people wasn't nearly as easy. Lester's first call went to Dustin Pedroia, the Red Sox's second baseman.

“As soon as he answered, he knew,” Lester said. “I lost it. I apologized to him. It's supposed to be one of the happiest times of my life, and I'm sitting there apologizing to one of my buddies.”

He rang David Ortiz and Mike Napoli and Shane Victorino, linchpins of the Red Sox's 2013 World Series win, along with Ben Cherington and Boston manager John Farrell. As much as they hated his choice, each understood. The Carmine offer created this mess, and the retooled Red Sox would enter the 2015 season with Pablo Sandoval and Hanley Ramírez, Rusney Castillo, and Yoan Moncada—nearly $320 million worth of bats—but no ace. They would finish in last place in the American League East division for the second straight year.

Toward the end of the night, the calls made and drunk on the thought of a new adventure, Lester wanted to celebrate with one last bottle of wine. He uncorked it and took a sip. John Henry was right. The Opus One tasted like heaven.

A
LL OF THIS—THE LETTERS, THE
gifts, the VIP treatment, and, ultimately, $155 million, every penny of it assured—for an arm that went through the showcase circuit and four years in the minor leagues, nine more in the major leagues, and a dozen spring trainings. I shouldn't have been surprised. Free agency supercharges the right brain in left-brained people.

Watching it unfold with teams blind to the inside of Lester's arm made it even more intriguing until the Cubs essentially shrugged their shoulders at the problem. Elbow injuries are so pervasive that a team run by two of the smartest men in the game, primed to make a strong run at the World Series over the next five seasons, was willing to guarantee nearly $26 million a year, at the time the second-highest number ever for a pitcher, to somebody it knew needed surgery.

“The chip doesn't bother me at all,” Epstein said. “It's not going to be debilitating. It can only fuck you for part of the season with bad timing.” To him, a bone chip was like a hamstring strain or an oblique tear, an injury with a finite recovery time and minimal long-term implications. And he was right: on the spectrum of elbow injuries, bone chips are what teams hope for when a pitcher complains of soreness. Recovery from bone-chip removal takes two to three months and doesn't involve the mental and physical drain of Tommy John rehabilitation. It's surgery, though, and it would add Lester to the brotherhood of scarred elbows, the long list of those at greater risk for a future injury.

“If the Cubs want me to get it removed, I'll get it removed,” Lester said. “If it's not bothering me and we don't want it to, I won't. It's one of those deals where I don't want to get cut on unless I have to. I don't want to get cut on to remove something that isn't a big deal. You never want to do surgery, regardless of how routine it is.”

It's not like the Cubs usually played fast and loose with the arm. When they went to Los Angeles to see free agent Masahiro Tanaka after the 2013 season, they declined to rely solely on Dr. Neal ElAttrache's report. They were the only ones to bring their team doctor so he could perform an examination. Both ElAttrache and the Cubs' doctor, Stephen Gryzlo, said Tanaka's elbow looked healthy. His UCL showed a partial tear less than six months later.

One of the lessons Epstein has learned in his thirteen years
running a baseball team: “You can't go into an MRI expecting it to be pristine.” Even when Gryzlo said his comfort level with Lester dictated only a three- or four-year contract—few team doctors ever will recommend a pitching contract longer—Epstein chalked it up to caution. Doctors exist to be skeptics. Executives exist to win baseball games.