by Tom Verducci
The obvious omissions from such a list, however, were the names of talented young pitchers. But Epstein and Hoyer did tell Lester he was just the first of two planned big-time additions to the rotation. Once the Cubs signed him, they told Lester, they would still have enough money to trade for another ace-level pitcher—they had their eye on Noah Syndergaard in the New York Mets’ system—or acquire one from what looked like a blockbuster class of free agents the next winter, including David Price, Jordan Zimmermann, Johnny Cueto, and Jeff Samardzija.
That’s when Epstein laid out the time line. The meeting with Lester took place 20 days after the surprising Kansas City Royals lost Game 7 of the World Series to the San Francisco Giants. The Royals punched their postseason ticket as an 89-win wild card team (they famously rallied against Lester and the Oakland Athletics to win that wild card game) after a 14-win improvement in 2013.
“We think we’re getting somewhere,” Epstein told Lester. “If you come here, in 2015 we have a legitimate chance to be the 2014 Royals. We should contend for the second wild card, and if things break just right, we could do some special things. We could also go in the other direction. We could crumble under the weight of relying on so many young players. But I don’t see that with this group.”
He told Lester the window was just beginning to open for the Cubs—that the team could contend for multiple championships over the next decade.
“We could present it in forceful, compelling terms because we believed it,” Epstein recalled. “We really believed in the talent and the character of this group. We could tell him that the Bryants, the Russells, the Schwarbers—these guys had the kind of makeup that was off the charts. We told him that we totally trusted in the ceiling and the character of these players and that this was the nucleus of a championship club.”
Lester would later say, “You never know when prospects work out and I know sometimes the free agents you want to go after sign extensions. So those plans don’t always work. But I believed in the core and the plans they have for more additions.
“I don’t really want to say it was a sales job, because I really believe what they believe, that this could be the next dynasty over the next six, seven, eight, nine years. That interested me. Having that comfort with Theo and Jed was important. I think I’m pretty good at knowing when it’s somebody you can believe or when you can see through the BS. I felt like there was no BS. This wasn’t a used car salesman sitting there trying to sell you something.”
Epstein ran Lester through statistical projection models and scouting reports on the young players in his system.
Said Lester, “It didn’t take much for him to convince me about these young guys. He sat there and gave me highlight after highlight and number after number on these guys and what they projected them to do and what position they wanted them to play. I think the biggest thing that sold me, especially on not only these young guys, but the whole organization, was just how arrogant he was about it, and I mean that in a good way. He was very confident in what he had done to this point or to that point to get this team to the next step, and I thought that was the most impressive part. Just how confident he was in these guys because these guys were not going to be failures.
“They weren’t going to be a bust when the scouting report gets out and going to get exposed and all that stuff. Now, getting to play with these guys, you really understand what he saw.”
Lester would later tell Epstein, “That day of the presentations was a home run. That’s when we started envisioning ourselves as Cubs.”
The meeting was all about hope. Nobody said anything about money. That would happen the next day.
The Cubs had money to spend on Lester because they had missed out on signing Japanese free agent pitcher Masahiro Tanaka 10 months earlier. Tanaka hit free agency after a 24–0 season for the Rakuten Golden Eagles. Interested teams would have to pay a $20 million posting fee to his former club and win a bidding war to gain Tanaka’s services. In January 2014, Tanaka’s agent, Casey Close, rented the Beverly Hills home of one of his colleagues, a basketball agent, to host two “recruiting days” for Tanaka. Representatives from 10 teams, waiting in black SUVs on the street for their one-hour turn over the two days, literally lined up in America’s leading neighborhood of $10 million homes to convince a 25-year-old pitcher, fresh off a flight from Japan and eating sushi on a couch inside one of the mansions, to take nine digits worth of their money.
Those 10 teams were not scared off by the obvious risks: that Tanaka had never thrown a pitch in the major leagues, that since he was a teenager his arm had endured a massive workload these same decision makers believe would wreck their own pitchers, and that the transition from playing baseball in Japan to playing in the United States was fraught with competitive and cultural differences that threatened the entire investment. The Yankees, Rangers, Astros, White Sox, Dodgers, Cubs, and Diamondbacks were among the teams that lined up.
“It was like The Dating Game,” said Kevin Towers, the Arizona general manager at the time. “First of all, it was a beautiful home. We were all waiting. You see all these cars parked up the street. And he’s sitting there on the couch and then it’s like, ‘Now it’s bachelor number one!’ You come down and try to sell yourself, your entire organization, in 15 minutes. You have a chance to make that first impression.”
The Yankees sent eight people to Beverly Hills. They brought a video presentation that included a recruiting pitch from former Yankees outfielder Hideki Matsui and a tour of Yankee Stadium done in the style of MTV’s Cribs. Twelve days later, Tanaka took the Yankees’ money: $155 million over seven years. With the $20 million posting fee folded in, their $175 million investment represented the second largest bet ever made on a pitcher at the time, trailing only the $180 million extension Detroit handed Justin Verlander. Rather than spend the money they had bid for Tanaka that winter, Epstein and Hoyer put it back in their pockets.
“Missing on Tanaka allowed us to do Lester,” Epstein said. “When we missed on Tanaka, rather than spend the money in the 2014 budget we set it aside. We rat-holed it and didn’t spend the $25 million [average annual value]. We said, ‘That will be a big part in pursuing a free agent.’ That became the signing bonus for Jon.”
The key question for Epstein was this: If Tanaka at age 25 was worth $155 million over seven years, how much money and how many years would he pay for Lester, who would pitch in 2015 at age 31?
The clues began in spring training of 2014, when the Boston Red Sox opened negotiations on an extension for Lester at four years and $70 million. The industry generally regarded that opening salvo as a lowball offer, particularly because Philadelphia had given left-handed ace Cliff Lee five years and $120 million four years earlier. If Boston regarded the offer simply as a start to lengthy back-and-forth negotiations, it was a miscalculation, because Lester, famously stubborn in how he pitches and approaches the game, told them he would not negotiate once the regular season began. Boston simply didn’t have the time to make up the chasm between its opening offer and Lester’s market value.
It didn’t help matters, either, when Red Sox principal owner John Henry expressed general agreement with a report that long-term contracts for pitchers in their 30s were bad investments. Boston wound up trading Lester to Oakland midway through the season, with designs on making a run at him after the season, though by then they had lost the advantage of incumbency and would have to line up with all others interested in his services.
The day after Epstein and Hoyer made their presentation to Lester, they put together a formal offer: $130 million over six years. How could they justify paying Lester through age 36 when the landscape was filled with bad investments on older pitchers?
“Contracts of this size for pitchers are a risk regardless of age, especially for starting pitchers in their 30s,” Epstein acknowledged at the time. “There’s no way around that. But I don’t believe that means you never do them. You go in with eyes wide open. [One] of our primary goals
was to build an organization that was so healthy that you don’t need to go into free agency very often, and healthy enough so you can afford to fail in free agency. You can’t sign a free agent if you can’t recover if you get little or no production.
“The only reason we can sign a contract like this is because of the potential impact position players we have in the organization. A good deal of our strategy is accumulating impact position players, and when the time is right to go out and get the impact pitching guys to go along with them.
“For three years we’ve slowly been building up a stable of position players and we knew sometime over the next 15 months we were going to add an impact pitcher or two from outside the organization, one through free agency and probably one through trade.
“It’s such a risky thing, but sooner or later you have to put your trust in someone. And when you’re a last-place team pursuing and attracting free agents, the free agents have to put their trust in you. We felt a lot better knowing the player. We’ve known Jon Lester since he was 18 years old. We studied his mechanics inside out.
“We believe nobody has perfect mechanics, but, according to the model we hold up when we send pitchers to biomechanical labs, his mechanics rate higher than anybody we’ve seen. Does that fully mitigate the risks? No, but it helps. And it helps knowing he’s been on a state-of-the-art shoulder [conditioning] program since he was 18, it helps knowing the family and the workload and what makes him tick. All that stuff helps. They are small factors in mitigating the risk. He has a tremendous pitcher’s body with ideal mechanics, he wasn’t abused as an amateur as a pitcher because of growing up in cold weather, and he has a very strong and undamaged shoulder.”
Epstein also knew that in Boston in 2009 he had ordered four MRIs of Lester’s shoulder before giving him a five-year extension. Those MRIs came back impressively clean. The two of them had a long shared history. Epstein and Lester had joined the Boston organization just three months apart a dozen years earlier.
In January 2002, Henry, Tom Werner, and Larry Lucchino agreed to join forces to purchase the Red Sox. One month later Henry divested himself of the Florida Marlins by selling them to Montreal Expos owner Jeffrey Loria, who in turn sold the Expos to the 29 other owners. Loria replaced many of the Marlins scouts and executives with the people who had worked for him in Montreal, leaving many of the former Marlins people to scatter to the wind. In March, many of them reunited with Henry in Boston, including evaluators David Chadd, Ray Crone, and David Finley, all of whom had been keeping an eye on a pitcher from Bellarmine Prep in Tacoma, Jon Lester. Epstein arrived in Boston from San Diego that same month as an assistant general manager. One of his duties was to assist with the draft.
Lester, who was throwing between 89 and 93 mph when his senior season began, looked like a first-round pick. By midseason, however, his velocity began to drop. When the Major League Scouting Bureau paid a visit to watch him pitch, Lester topped out at 88 mph. When that video circulated, Lester’s stock sank. But Chadd, Crone, Finley, and Gary Rajsich, the Boston area scout, all had seen Lester on his best days, and they knew that a high school pitcher who also played another position (outfield) and who also played other sports (basketball and soccer) might typically hit a dead-arm period during the season. They were unbowed by the Scouting Bureau report.
That June, the first draft for Epstein with Boston, the Red Sox did not have a pick until number 57, in the second round. Much to their good fortune, Lester slipped to them. They signed him for $1 million.
Four years later, on June 10, 2006, Lester made his major league debut. He was spectacular right from the start. Lester, then just 22 years old, went 5–0 with a 2.38 ERA in his first eight starts. But then he hit a rough patch. His back began to ache. On August 18, while Lester was driving to Fenway Park for a start against the Yankees, a car rear-ended his vehicle. He gave up seven runs that night before getting knocked out in the fourth inning. His back grew worse. He lasted just five innings in his next start, giving up three runs against the Angels in Anaheim, after which he flew to Seattle to see his doctor about his back.
After that exam, Henry arranged for a private jet to take Lester back to Boston for more exams. It wasn’t simply about his back any longer. On Thursday, August 31, the Red Sox announced that Lester had been admitted to Massachusetts General Hospital with enlarged lymph nodes. The next day the club announced that he was diagnosed with a rare form of non-Hodgkin’s lymphoma, a blood cancer, and would immediately begin treatment. They’d found it early. In late November 2006 he was declared cancer free.
Lester spent the first half of the 2007 season in the minor leagues, regaining his strength and his form. He earned a second-half promotion, and was the winning pitcher in the clinching game of the 2007 World Series—just 13 months after his cancer diagnosis.
After that, and up to his free agency, Lester proved to be one of the best and most reliable pitchers in baseball. From 2008 through 2014, Lester averaged 15 wins and 2071⁄3 innings, ranking fourth and sixth among all pitchers over those years in those respective categories. He kept up his velocity with his clean mechanics. In those years Lester’s fastball maintained an average velocity in the narrow range of 93.1 to 94.7 mph.
Meanwhile, while trying to sign Lester, Epstein and Hoyer were running concurrent negotiations with a soon-to-be-38-year-old backup catcher who hit .184 in 2014 while starting only 47 games, 18 of them with Lester on the mound for Boston. David Ross, despite his modest statistics, was a free agent in demand because of his reputation as an excellent receiver with impressive leadership skills. For anyone interested in signing Lester, Ross had the added benefit of having established himself as the left-hander’s personal catcher.
What became one of the most renowned pitcher-catcher relationships in baseball began in earnest on September 3, 2013, in Boston. The first-place Red Sox began play that night with a 51⁄2-game lead in the AL East, though they had been shut out the previous night by Detroit, the AL Central leaders. Lester had thrown much of that season to catcher Jarrod Saltalamacchia. Ross had missed much of the season with complications from concussions, which sometimes left him in such dark moods that he would find himself snapping at other people while driving with his wife and kids in the car. Manager John Farrell that night put Ross behind the plate for what was only his fourth start in 13 games since coming back. The fun started when Ross and Lester began going over the scouting report on Detroit.
“We all have different days,” Lester said. “We all have good days, we all have bad days. You’re in a good mood, you’re in a bad mood, whatever. He was in one of those David Ross bad moods and we went over the report and it was like, ‘This guy, he’s got it. He’s got it under control.’ I can just sit back and just see what he wants and I’ll throw it, you know what I mean? So it just so happened we had a good start.”
Lester and Ross combined for seven innings with one run allowed. Boston won, 2–1. Still, Farrell continued to mix Saltalamacchia and Ross behind the plate for Lester’s starts. It wasn’t until the American League Championship Series that year that Farrell fully committed to Ross as Lester’s personal catcher. The results were stunning. Starting with the September 3 game against Detroit and until his trade to Oakland, Lester went 15–5 with a 1.99 ERA in the 25 games Ross caught him.
Speaking about Ross’s thoroughness and intensity, Lester said, “Going into the [2013] postseason, I just felt like that wore off on a lot of our pitchers. That intensity, and where he wanted the ball, and he expects so much out of you that you want to almost do more sometimes to kind of get that approval-from-your-dad type thing. And it just evolved from there.”
Epstein put in an early call to Ross when the free agent period began after the 2014 season. He told Ross he was trying to sign Lester.
“We definitely have interest in you, Lester or no Lester,” Epstein told Ross. “We’re going for it. If we get Jon, we’re definitely going for it. If we don’t get Jon, we’ll wait one more year to go for it.
We’ll be 80 percent in this year and with one more off-season we’ll be all-in.”
The Red Sox wanted to keep Ross. The Padres made a strong push for him. Meanwhile, Epstein arranged for Ross to get his personalized version of the Cubs’ recruitment video. In that one, the public address announcer at Wrigley Field announced his name for his turn at bat in the World Series.
“I got chills watching it,” Ross said. “Theo laid out the plan to me. When Theo started talking to me, I started thinking, What if I was on the team that won the Holy Grail of championships? If you win that, you’re set for life. You sign autographs the rest of your life, like guys like [Kevin] Millar and [David] Ortiz with the ’04 Red Sox.
“If you could be a part of all that, why wouldn’t you try? If you really want to compete at the highest level, that’s the biggest stage. That’s what was calling me. I’m a guy that lays out the pros and the cons, but when it came to which way my heart was going, it kept pulling me to Chicago.”
Ross would have to wait. Lester was the Cubs’ priority. Epstein and Hoyer moved quickly with their November 19 offer to Lester, and soon thereafter bumped it from $130 million to $150 million, “hoping for an impulse buy,” as Epstein put it. Even so, the pitcher’s representatives, Sam and Seth Levinson, formulated their own game plan. They wanted to slow-track negotiations so that Lester remained in play until the winter meetings in early December, when an auction atmosphere can take root while teams gather under one roof for the equivalent of baseball’s annual convention.
Other teams began to jump in. On December 1, Lester’s doorbell rang. He opened the door and heard the man standing there say, “Hi, I’m Buster Posey, and I want to be your catcher for the next six years.” Posey, the San Francisco Giants catcher, had driven three hours from his Georgia home. He was accompanied by Giants president Larry Baer, general manager Brian Sabean, and assistant general manager Bobby Evans. The Giants had just won their third World Series title in five seasons.
