The Arm (14 page)

“Listen, we believe relationships can get better and stronger with bumps in the road,” Cherington said. “No marriage is perfect. That's why we're here, and we want to put everything behind us.”

The awkwardness soon abated. Lester was reminded why he loved Boston. Then it was Larry Lucchino's turn to speak. Lucchino is one of baseball's most polarizing figures, known as much for his loutishness as his business acumen. He liked to bloviate,
often to his team's detriment; he was the first to call the Yankees the “evil empire.” But he sparked baseball's retro-park revolution when, as president of the Baltimore Orioles in the early 1990s, he facilitated the construction of Oriole Park at Camden Yards. Under his stewardship, Fenway Park went from dump to jewel.

Following the 2008 season, the Red Sox longed for first baseman Mark Teixeira. Lucchino, Henry, and Epstein flew to Dallas for dinner with Teixeira and his agent, Scott Boras, convinced they could hammer out the particulars that night. Before the appetizers arrived, Lucchino, sitting across from Teixeira, told him no team would beat the Red Sox's $162 million offer, so there was no sense in shopping for another team. Shortly after dinner ended, Boras was on the phone with the Yankees. Teixeira signed with them a week later for $180 million.

At Lester's house, Lucchino tried to play humorist. “We know that you love Boston,” he said. “We know your kids love Boston. And, heck, Jon, you're a Southern cracker despite being from the West Coast.” Everybody laughed. Some of the chuckles were more uncomfortable than others. Lucchino talked about the support system the Red Sox would have in place—how they were bringing back Bob Tewksbury, the team's former sports-psychology coach who was working at the Major League Baseball Players Association. Cherington shot a dirty look Lucchino's way. That wasn't public yet. The Red Sox were sworn to secrecy.

The one voice nobody had heard pierced the quiet. John Henry is the Red Sox's majority owner, the analytical complement to Lucchino the lawyer and Werner the politician. Henry had made billions trading commodities, and since buying the Red Sox in 2002 had expanded ownership's empire to include an English soccer team, Liverpool, and a three-car team in NASCAR. Even though he once said Lucchino runs the Red Sox, Henry ran Lucchino. His words in an April 2014
Bloomberg Businessweek
story had stuck with Lester. Henry, riffing on a paper presented at the annual MIT Sloan Sports Analytics Conference that reaf
firmed the value of young players and slagged those paid for past performance, was quoted as saying: “To me, the most important thing this study shows is that virtually all of the underpaid players are under thirty and virtually all the overpaid players are over thirty. Yet teams continue to extravagantly overpay for players above the age of thirty.”

Henry now claimed he had been misunderstood. “We have no biases for players signing in their thirties,” he told Lester. The Red Sox have spent the second most money in baseball behind only the Yankees since Henry bought the team, he noted, and the resources existed to continue that. No more transition years, like 2014, when the Red Sox's reliance on young talent contributed to their last-place finish.

Cherington went for the close: Even though the Red Sox did prefer shorter contracts for older players, they wanted to dispense with protocol for Lester. Cherington pulled out a folder with a white envelope.

“This is for you, Jon,” he said.

Lester took the envelope and thanked Cherington. Everyone else stood up and exchanged pleasantries. The meeting was over. After the Red Sox brass left, Lester tore at the envelope and pulled out a piece of paper. His eyes flitted across the page, looking for the offer: six years, $120 million. Two more years and $50 million more, all because of two bets. The first was that Lester had bet on himself. The second was that baseball believed in his arm. Because of Lester's time in Boston, the Red Sox were the only team in baseball that knew something might be amiss inside his elbow. And they still offered him one of the ten biggest contracts ever for a starting pitcher.

T
HREE DAYS BEFORE LESTER'S MEETING
with Boston, the Levinsons had been in Mesa, Arizona, at the Cubs' opulent spring-training complex. They locked down specifics for their meeting—Epstein
and Hoyer wanted to host Lester in Chicago—before heading to catch a few innings of the Arizona Fall League game being played inside the stadium.

Epstein stood in between the Levinsons in the concourse, directly behind the home-plate seats where scouts and other personnel sat. He looked down and recognized Ben Cherington, who sat alongside lieutenants Brian O'Halloran, Zack Scott, and Jared Porter, the team's director of pro scouting. Cherington could be serious, so Epstein pulled out his phone and tapped a text message to Porter.

“Do the Levinsons have any good clients?”

“Lester,” Porter replied.

“Oh,” Epstein wrote, “I heard he's good.”

“Morse, Badenhop, Janssen, McGowan,” Porter continued, ticking off four other ACES free agents.

“Look back and to the left,” Epstein wrote.

Porter turned around and saw a smiling Epstein, his left arm around one Levinson, his right arm around the other.

Over the previous dozen years, Epstein had carved himself a unique place among baseball executives. He was not the Houston Astros' Jeff Luhnow, a wheel-reinventing swashbuckler intent on upending the system. Nor was he the Arizona Diamondbacks' new GM, Dave Stewart, a scouting hardliner who believed numbers were best left inside calculators. And he certainly was not a cross-cultural icon like Billy Beane, with Brad Pitt clamoring to portray him in a movie. Epstein took a sliver of each to form the archetypal modern GM: he was just as comfortable arguing the value of analytics all day as he was breaking down an on-the-ground scouting report or joining Eddie Vedder for his fiftieth birthday party in San Francisco.

The cult of Theo was powerful. Hoyer had left the GM job with San Diego—a position with more decision-making power—to join Epstein in Chicago. He was the conscience on Epstein's shoulder, the confidant who challenged him most, as
close to an equal partner as Epstein would allow himself. When they arrived in Chicago for what would be a massive rebuild—a top-to-bottom reimagining of how the organization runs, with a sell-off of every valuable asset they couldn't sign to a team-friendly long-term deal and a focus on larding the team with hitting prospects to counteract the offensive drought they saw beginning to plague the game—they first needed to implement a new worldview. The Cubs scrapped the idea of a hierarchical office and set it up more like a boiler room, open and democratic, willing to accept every idea so long as it could be challenged and dissected by the brains with which they stuffed the room.

Never did Epstein and Hoyer figure one of those ideas would be Jon Lester. There weren't many sure things in baseball, but Lester re-signing with Boston was one. Then came the offer in the spring of 2014, and the moment it leaked, the Cubs recognized just how game-changing it was. “We'd look at the free agent list and be like, ‘Eh, Lester is never going to be a free agent,'” Hoyer said, “and so it really wasn't until the whole thing in spring training that we said this actually could happen. Even then, I don't think we really thought it would.”

Still, it warranted due diligence, and when Epstein and Hoyer asked their scouts, analysts, and other bright minds in the organization, they agreed almost unanimously: Lester was the target, more than Scherzer or the other front-end free agent starter, James Shields. Lester checked almost every box on their wish list. Left-handed pitchers age better. Strong mix of pitches without an excessive reliance on velocity. “Perfect mechanics,” Epstein said. Off-the-charts makeup. Playoff dominance. From the start, Epstein and Hoyer figured Lester would fetch at least a six-year deal, so in the annual survey sent to all Cubs personnel, they asked: “Under any circumstances would you ever go six years, $100 million-plus on a free agent pitcher?”

Answers ran the gamut. Coaches, minor league managers, and scouts were more of the hell-yes variety while in-house sorts
weren't quite as keen. Depending on the day, Epstein and Hoyer found themselves on both sides. “Unless you think you've got it all figured out, which no one does in baseball, you have a lot of back-and-forth in your own head about it,” Epstein said. “You try to balance different factors. You wake up one day like, ‘We've got to sign Lester,' you wake up another day, ‘We're never signing a pitcher in his thirties,' and it's an internal struggle. Jed and I had the back-and-forth with each other. We changed each other's minds. It's a process of getting to the least bad answer.”

For all of the front office's success so far—the emergence of the greatest collection of prospects in the game was enough to make a lot of people forget the Cubs' 286 losses over their first three seasons in Chicago—Epstein and Hoyer were far from infallible. They operate by a mantra: “We don't know shit.” The biggest contract they'd ever given to a pitcher was to Daisuke Matsuzaka, a six-year, $103 million deal with the Red Sox, for which they got 668 middling innings before his UCL gave out. The history of the $100 million pitcher, from Mike Hampton to Barry Zito to Johan Santana, was littered with disappointment.

On a conference call with Cubs chairman Tom Ricketts and his siblings Laura, Todd, and Pete, Epstein and Hoyer laid out the strategy. All their young, cheap players gave them room to splurge on the frontline starter their farm system lacked. So here's how Lester fit. Here's the market. Here's the personal connection. Here's the downside. Here's why he's the right guy at the right time. Here's how high they'll go. Here's the first offer.

Settling on that number took time. Unlike Carmine, the Cubs' computer system, named Ivy, looked at Lester in far friendlier fashion. It said $120 million over six years was more than tolerable. The Cubs could adjust the model to rationalize $150 million, the ceiling Epstein and Hoyer suggested. Their ability to hunt for bargains convinced the ownership that Epstein and Hoyer could root out the extra $30 million elsewhere. The Rickettses told them to go get Lester.

Step one: the perfect pitch for their perfect pitcher. For more than a year, the idea of a Cubs infomercial bounced around the office. They had considered making one to lure Robinson Cano, the jewel of the 2013–14 free agent class, until they came to a grim realization. “We had nothing to put in the video,” Epstein said. The rise of homegrown talent like Kris Bryant, Addison Russell, Jorge Soler, and Kyle Schwarber, along with the emergence of ace Jake Arrieta, the hiring of the first-rate Joe Maddon as manager, and the unveiling of the renovation that would bring Wrigley Field into the twenty-first century, changed all that. “We've got a pretty good story to tell,” said Epstein, who supervised multiple cuts of the video and fired off emails with changes and fixes throughout October.

On November 4, the first day of free agency, Lester received a DVD copy of the video along with a letter from Epstein and Hoyer that said: “We are not going to hide the ball: you are exactly the type of pitcher AND person we want wearing a Cubs uniform.” The fifteen-minute video might as well have been titled
Propaganda Explicitly for Jon Lester
. “Everything we did,” Epstein said, “was just meant to appeal to a deep layer of Jon and Farrah's psyche that maybe they weren't aware of.”

In the video's first two minutes, Epstein talks about how the team staffs a twenty-four-hour on-call doctor and nurse for families in case of emergency when the team is out of town. First baseman Anthony Rizzo touted Tom Ricketts as an Everyman who drinks beers with the fans. Epstein extolled the spring-training complex in Mesa. Ricketts itemized the Wrigley Field renovations and improvements. Quotes from writers Buster Olney, Rany Jazayerli, and Dave Cameron exalted the team's young core. Ryan Dempster, a longtime Cub and teammate of Lester's in 2013, waxed on about how the Cubs' large number of day games allowed more time with family. Helicopter shots of the busy city and the quiet country an hour away were aimed at Lester's rural tastes. And around the eleventh minute, Rick Sutcliffe, a Cubs
star in the '80s and now an ESPN broadcaster, popped up to say: “I don't think I can even put into words what Chicago is going to be like when they win the World Series.” The video ends with clips from a commercial for the video game
MLB 12: The Show
that imagines the hysteria of a Cubs championship, with parties in the streets and a jubilant vendor kissing a fan.

The day of the meeting started with a whimper. Lester's flight from South Carolina into Chicago was delayed for three hours. He and Farrah hopped in a car at O'Hare, which the Cubs stocked with a case of beer and a handwritten note apologizing for their travel issues. After leaving their bags at the hotel, they were dropped off at the Cubs' makeshift offices across the street from the under-renovation Wrigley Field and spirited into the one presentable space, a conference room with modular clocks, soft carpeting, recessed lighting, and a thermostat set at 72 degrees. At Hoyer's suggestion, Lester's career batting statistics—.000, hitless in 36 at bats—had been posted on a faux scoreboard. It got a hearty laugh from Lester and Farrah, the perfect icebreaker. Twenty minutes into the meeting, she was sipping a glass of wine, Lester, Epstein, and Hoyer were drinking beers, and it felt like old times to everyone. Ricketts was supposed to present first, but he had skipped the meeting because he refused to miss his daughter's school play. The Lesters appreciated that.

Cubs charity czar Connie Falcone explained how the team could support NVRQT, traveling secretary Vijay Tekchandani boasted that the Cubs would travel the fewest miles of all teams in 2015, and media relations director Peter Chase promoted the virtues of the Chicago press corps compared with that of Boston, where Chase once worked as well. Epstein and Hoyer then broke down the Cubs player by player, trying to explain their vision and allay Lester's anxiety over joining a team with a losing tradition.