The Executive: How One Man has Changed the Course of Two of Baseball’s Premier Franchises
In the wake of the 2002 regular season, the Boston Red Sox were entering a time of great uncertainty. The club had just finished up an extremely disappointing season where they had an impressive 93–69 record, yet failed to make the playoffs. Off the field, things were just as hectic. When they had bought the team prior to that season, new owners John Henry, Tom Werner, and Larry Lucchino had failed to find a person skilled enough to run the day to day baseball operations of the team. The group believed that in order to win the franchise’s first championship in over 80 years, a new voice had to be in charge.
That new voice was found when Lucchino hired the 28 year old Yale University graduate Theo Epstein to be the team’s new General Manager. Nearly every front office in Major League Baseball was shocked to learn that Lucchino was able to place so much trust in a man who they all saw as “just another know-it-all kid” who was now the youngest executive in the history of the sport. However, soon these detractors were no longer shocked by how young Epstein was, but by how well he was able to do his job.
During that first offseason, Epstein wasted no time signing three minor free agents who would end up playing a major impact in the team’s World Series run the following season. These players were none other than the power hitting David Ortiz from the Minnesota Twins, the loud mouthed, Jack Daniels chugging first baseman Kevin Millar from the Florida Marlins, and Cy Young Award winner Curt Schilling from the Arizona Diamondbacks, who, in the most successful Wine-and-Dine in professional sports history, was persuaded to join the club after Theo flew to his house on Thanksgiving Day and ate dinner with his whole family.
An often overlooked fact is also just how well Theo Epstein was able to prepare the Red Sox for the future through the draft. Sure in Major League Baseball the draft isn’t aired on prime time television and there’s usually no controversies except for the occasional mispronounced name and wardrobe malfunction from the Commissioner (I’m sure we’re all still scarred by the horrifying Bud Selig nip slip of 20o6), but that doesn’t make it any less vital to the success of teams moving forward. Theo knew that to ensure the long term prosperity of the club, there needed to be a constant flow of young talent entering the system.
During his tenure as General Manager, Epstein was able to draft Jacoby Ellsbury, Dustin Pedroia, Clay “I can’t pitch through July without getting injured” Buchholz, and Jonathan Papelbon, all of whom ended up playing a major role in the team’s championship in 2007 and beyond.
Before he left to become the President of Operations for the Chicago Cubs, Epstein was also able to draft a large group of the core players who make up the the 2016 Red Sox including Xander Bogaerts, Mookie Betts, Jackie Bradley Jr., and Blake Swihart.
But in 2011, Theo moved on to greener pastures, and of course by greener pastures I mean a team that hadn’t won a World Series in over 100 years and a city that gets so miserable during the winter that it could be a backdrop for the latest Hollywood dystopian action movie. (Author’s note: Just remembered the book/movie “Divergent” so I definitely nailed that comparison).
In Chicago, Epstein was handed a seemingly impossible task of turning a team of ragtag rookies and overpaid veterans into a team that would not only be able to make it out of the buzz saw that is the N.L. Central, but a team that would be able to compete and win when the lights shined the brightest. Despite those odds being seemingly stacked against him, in less than five short years since taking over club’s baseball operations, Epstein has done just that. Using all of the lessons he learned over the course of tenure with Boston, he has manufactured the Cubs into a team that is a top contender to win the National League in the present day and for many years to come.
By using a brilliant combination of Moneyball-esque sabremetrics and good old fashion scouting, Epstein, along with new manager and baseball wizard Joe Maddon, have assembled a team that will be in serious contention for a championship come October. This 2016 version of the Cubs is a melting pot of seasoned veterans, and former Red Sox, Jon Lester, John Lackey, Anthony Rizzo, and David Ross. They have also been jolted by free agent signings like last year’s NL Cy Young Jake Arietta, Jason Heyward, and Ben Zobrist. Also, similar to what he did in Boston, Epstein has also been able to retool what was once an abysmal Cubs farm system into one of the best in baseball. The fruits of this system have already began to show with the likes of players like Kris Bryant, Jorge Soler, and Addison Russell, who are all having a major impact on the team’s success.
On paper, this Cubs team is something special, as is proven by the fact that as of yesterday they are the first team in baseball to reach 40 wins, a pace that hasn’t been seen since the 2001 Seattle Mariners who won an MLB record 116 games. Those Mariners of course fell short of winning a World Series, a situation that these Cubs are well aware of and will try their hardest not to repeat. However, if this year the Chicago Cubs do win their first championship since the great Bull Moose Teddy Roosevelt was president and cars were still considered so dangerous that the speed limit was a tire scorching 10 miles per hour, they will have one man to thank and one man only. Theo Epstein.
