Late on Dec. 9, Giants assistant GM Bobby Evans told reporters he thought his club was out of the Jon Lester sweepstakes, that the lefty’s heartstrings were pulling him toward two finalists: the Red Sox and the Cubs.

Done deal.

It was a negotiation of sentimental currency, and Boston was flush. He was drafted here, beat cancer here, won a World Series here and then did it again a few years later. Chicago had Theo Epstein, a mess of raw bats and a 106-year tradition of blowing it. Advantage: Sox.

Only, in this battle for Jon Lester’s heart, Ben Cherington never had a chance.


Epstein was in his second season as General Manager of the Red Sox in Nov. 2003 when he flew to Arizona to spend Thanksgiving with Diamondbacks ace Curt Schilling, the last piece to his World Series puzzle. The Red Sox had worked out a deal with Arizona to bring Schilling to Boston, provided he waive his no-trade clause and sign an extension.

By Black Friday, it was done, almost a year to the day after Larry Lucchino made the 28-year-old Epstein the youngest-ever GM in Major League Baseball.

Epstein was home-grown talent, born in New York but raised in Brookline on a steady diet of being disappointed by the Red Sox. A baseball lover but an unspectacular player, Epstein’s brain took him to Yale University. At 18, he landed an internship with the Orioles. It was there he met and befriended Lucchino, then part of Baltimore’s organization. A few years later, Lucchino brought Epstein with him when he became president of the Padres. When Lucchino came to Boston in 2002, so did Epstein.

Sabermetrics were at the time largely in the shadows, but a few forward-thinking baseball leaders had started to embrace the arcane formulas, new principal owner John Henry among them. He hired the “father of sabermetrics,’’ Bill James as a consultant and pursued stat whiz Billy Beane for the vacant GM position but was rebuffed. At Lucchino’s suggestion, the stat-crunching Ivy Leaguer got the job.

Jon Lester’s history with Theo Epstein likely played a big part in his leaving Boston for Chicago. —AP


Epstein’s first signings included a few value bats who would make an impact in the World Series in Bill Mueller, Kevin Millar and a little-known first-baseman/DH for the Minnesota Twins named David Ortiz. Epstein’s first calendar year at the helm was tame, but the 2004 season would be anything but.

He had taken the job with the intention of bringing Boston its first World Series title in 86 years, and it became clear to him by mid-summer the team’s defense was not ready for the postseason. In a blockbuster deadline swap, Epstein moved beloved shortstop Nomar Garciaparra for a pair of Gold Glove players in shortstop Orlando Cabrera and first baseman Doug Mientkiewicz. It was the sort of gutsy move that could have led to a swift ouster had it failed. But of course, it didn’t.

Epstein became a fan-favorite after the World Series win, but he and Lucchino reportedly clashed over power throughout the 2005 season. Negotiations grew heated, and Epstein’s contract expired on Halloween night, with the kid GM reportedly sneaking out of the complex in a gorilla suit. Epstein stood his ground, and returned to the club ten weeks later with expanded powers.

Throughout the mid-2000s, Epstein’s front office drafted and nurtured the pieces that would form the nucleus of the 2007 World Series run and subsequent success, including Dustin Pedroia, Jonathan Papelbon, Jacoby Ellsbury, and Kevin Youkilis. Lester was drafted months before Epstein’s hiring, but Epstein presided over his ascent.

Epstein presided over an unprecented run for the moden Red Sox, but it came to a crashing halt in 2011 when the Red Sox squandered a nine-game AL East lead and missed the playoffs. In the aftermath, the front office and longtime manager Terry Francona made the mutual decision to part ways. Shortly after, Epstein became the Cubs’ president of baseball operations.


Long-time front office man Ben Cherington was promoted to fill the vacancy. In addition to serving in scouting and player development, Cherington had been co-interim GM with Jed Hoyer during Epstein’s earlier hiatus.

Cherington was widely viewed as a puppet of ownership despite their frequent suggestions to the contrary, and the hiring of Lucchino favorite Bobby Valentine only served to reinforce that perception.

His first season was a predictable disaster, but held two moves that would play into the success that was 2013: the shedding of nearly $300 million in salary between Carl Crawford, Josh Beckett and Adrian Gonzalez and the firing of Valentine a day after the regular season ended.

Where Epstein went with his gut, Cherington was all business. In the 2013 pre-season, his Red Sox made a series of smart, safe moves that included the hiring of former Red Sox pitching coach John Farrell as manager and bargain signings of David Ross, Mike Napoli, Shane Victorino, Koji Uehara and others.

These acquisitions and others meshed perfectly with the existing nucleus of the squad, creating an atmosphere in the clubhouse not seen since 2004 and its ‘band of idiots.’ At the end of October, the Red Sox were world champions for the third time in 10 years.

A minor player in the 2007 World Series, Lester was a full-fledged ace in 2013. He threw 34.2 innings of 1.56 ERA ball in the postseason, winning two in the World Series and four overall. With his contract set to expire at the end of the 2014, an extension was priority no. 1 — for everyone but the Red Sox front office.

At the Baseball Writers Association of America awards dinner in January, Lester told reporters he would take a discount to stay in Boston. Cherington took him at his word and then some, offering four years at $70 million — less than half of the $155 million he would sign for on the open market. Talks broke down, and Lester was traded in a deadline deal that he would later say helped him stomach the idea of leaving Boston.

In his introductory press conference as a Cub earlier this month, Lester said Epstein’s selling point was a new dynasty in Chicago. A suspect claim at face value, but given the man making it, he bought in. At the same press conference, Epstein joked he would have soaked himself in deer urine — as a hunter does to attract his quarry — to bring in Lester. As Schilling was a decade ago, Lester was Epstein’s guy, and that meant something.

It remains to be seen whether this signing is a savvy one or Epstein’s sentimentality getting the best of him. It’s impossible to argue Lester’s resume, but at 30, it’s unlikely he remains a workhorse through the duration of what could be a seven-year deal. Epstein set aside conventional wisdom to follow his heart, but he’s been burned by that in the past, as he was with Carl Crawford, Josh Beckett and others.

Hanley Ramirez, who became a Red Sox in November, was one of the biggest free agent signings of Ben Cherington’s tenure as GM. —The Boston Globe

Looking strictly at trophies, Cherington has clearly had a better first three years than Epstein. But the latter still deserves plenty of credit for a World Series won on the shoulders of David Ortiz and Jon Lester.

Cherington this off-season made the first big-money free agent signings of his tenure, bringing in the proven (and popular) Pablo Sandoval, former Sox top prospect Hanley Ramirez and pitchers Rick Porcello and Wade Miley, who have been heralded as possible blossomingstuds.

Cherington has shown he can tweak a competitive major league roster to keep it that way, but whether he can build a World Series roster on his own has yet to be seen. He lost on Lester and has taken a beating for it, but the jury on that trade is still years from a verdict.

At this stage, only one thing is for sure: Cherington is no Theo, for better or worse.