Theo Epstein has ended one decades-long World Series championship drought. And now, he’s the brains behind the end of a second. The Chicago Cubs have won their first World Series since 1908 and he’s definitely getting paid for that.
Epstein was the general manager of the Boston Red Sox when the Sox won the World Series in 2004, reversing the so-called Curse of the Bambino and claiming their first title since 1918. He left Boston for Chicago before the 2012 season, and four years later, he’s led the Cubs to their first National League pennant since 1945. Since they beat the Cleveland Indians in the World Series, they ended the longest championship drought in professional sports.
The Cubs didn’t get off to a hot start in the Series, losing Game 1, 6-0. However, they ended up coming all the way back from a 3-1 deficit to force a Game 7 on November 2. They won, 8-6 in 10 innings.
Epstein, who grew up a diehard Red Sox fan in the Boston suburb of Brookline, has an estimated net worth of $25 million, Celebrity Net Worth notes, and is among the highest-paid baseball executives.
Here’s a look at Epstein’s recent contract extension and his past deals:
1. Cubs & Epstein Agreed to a 5-Year $50 Million Deal in September
Just before the 2016 postseason kicked off, the Cubs announced that Epstein signed a five-year deal to stay with the franchise. USA Today reported that the deal is expected to be worth over $50 million.
Cubs chairman Tom Ricketts made it clear that he wanted to make Epstein the highest-paid executive in baseball.
“He’s the best at what he does in the game,” Ricketts said in February. “And from a compensation standpoint, it should be reflected. We’re generally on the same page. We spend a lot of time together, not just on the contract.”
Epstein’s contract is much higher than another recent big executive deal. In October 2014, the Dodgers’ Andrew Friedman signed a five-year, $35 million deal.
2. 2016 Was Epstein’s Last Year in a 5-Year, $18 Million Deal Signed in 2011
Epstein’s new contract is a significant pay raise. In 2011, ESPN reported that Epstein’s first deal with the Cubs was for five years and worth between $15 million and $20 million. The Cubs also agreed to pay the conclusion bonuses from his Red Sox contract.
Epstein jumped to the Cubs with one year left on his last Red Sox contract. He had been in Boston for nine years.
The compensation deal between the Cubs and Red Sox for Epstein going to the Cubs included the Sox receiving pitcher Chris Carpenter and the Cubs getting first baseman Jair Bogaerts. Bogaerts is Xander Bogaerts’ twin brother, but did not meet the same success as Xander and never played in the Cubs’ system.
As for Carpenter, he appeared in eight games for the Sox in 2012 and hasn’t pitched in the majors since.
3. Epstein Left the Red Sox for 3 Months in 2005 After Being Offered a 3-Year, $4.5 Million Contract
In 2005, Epstein famously left the Red Sox for three months after he received a three-year contract offer that would have earned him $1.5 million a year. According to ESPN, this was quadruple what he was making before. However, it was short of the $2.5 million annual salary the Sox had offered Oakland GM Billy Beane in 2002. (Beane ultimately turned down the Sox and that’s why they hired Epstein.)
At the time, The Boston Herald reported that the money wasn’t the real reason he left. It was the inside politics with the Sox and his boss and mentor, Larry Lucchino. The night Epstein resigned was Halloween, so he was famously seen leaving Fenway in a gorilla costume.
Before the 2006 season began, Epstein and the Red Sox came to terms and he resumed his title as GM for the team.
4. Epstein & His Brother Paul Co-Founded the Foundation To Be Named Later
When Epstein isn’t hard at work in Chicago, he and his twin brother Paul run The Foundation To Be Named Later. They co-founded the foundation in 2005 with a mission to promote education and the healthy development of youth and families. The fund provides the Peter Gammons College Scholarships and several other Boston and Chicago-based beneficiaries.
They also host the Hot Stove Cool Music benefits, which often include Epstein himself playing guitar. In June, Pearl Jam’s Eddie Vedder performed at a Chicago Hot Stove cool Music concert and also auctioned off one of his guitars for $26,000.
5. In 2011, Epstein Bought a Home in Chicago Near Wrigley for $3.25 Million
When Epstein moved to Chicago in 2011, he bought a $3.25 million home located near Wrigley Field, so he doesn’t have a long commute. Crain’s reported at the time that the home was listed publicly as the residence of his wife, Marie Whitney Epstein.
The home was built in 2010 by PLD Homes and was originally listed at $3 million in September 2011. The home is 7,800-square-feet and is three stores. It has four fireplaces, a master bedroom, a four-car garage, a patio and deck.
The Chicago Tribune reported at the time that there was a bidding war for the home. Patrick Sharp, who was still with the Blackhawks at the time, was set to buy the house, but he canceled the contract five days before Epstein closed the deal.