Theo Epstein Delivers Master Class In Business of Baseball

by  |  February 19, 2019

JohnLaLoggia

Theo EpsteinIf you’re curious about what makes a great baseball executive, take a look at the press conferences conducted by Chicago Cubs President of Baseball Operations Theo Epstein. You won’t find too many public speakers who are more eloquent or effective at getting their message across than him.

During the 2018 end-of-season press conference, he spoke about his team’s abrupt ending after falling to the Rockies in the NL Wild Card game. There was a variety of diverse issues he addressed, ranging from a sudden lack of offense to domestic violence. His reputation and accomplishments are well renowned, but his public speaking is the stuff of legends.

Accountability

Despite winning 95 games and going to the playoffs for the fourth year in row, the 2018 season was seen as a disappointment considering the large payroll and young talent. The team squandered a five-game lead to the Brewers during the last month of the regular season to lose the division. Many of their young players regressed as the season went along. There were two offseason acquisitions that were unsuccessful. Free agent Yu Darvish signed a six-year, $126 million contract in February 2018. He pitched only 40 innings and was shut down for the year with an elbow injury by late August. Tyler Chatwood signed a three-year deal worth $38 million. In 2018, he walked 95 batters in 103.2 innings, pitched to a 5.30 ERA and was moved to the bullpen in late July.

It times of turmoil, we’ve often seen people in high-ranking positions deflect blame or deny things aren’t as bad as they seem. Every time Theo Epstein faces a difficult question, he meets it head on with supreme confidence.

“We all have to be accountable, and it starts with me.”

It’s simple, yet effective. People want a leader who is upfront about their mistakes and takes ownership of them. Epstein’s ability to relate to the media looks effortless, not because he gives a juicy soundbite, but because he conveys humanity to the public.

 “When you fail and you don’t reach your goal, it starts with self-awareness, self-reflection and accountability.”

People like to hear someone who is confident, but they love to hear someone who is humble. Theo Epstein’s empathy and humility is why people respect him and the media praises him. Baseball is a war of attrition and it takes a lot of moving parts to win. He acknowledges the complexity of the game which gives him immediate credibility. Baseball’s media and journalists are simply looking for the truth, and Epstein provides that. What the media feasts on is someone lying, unprepared, or not taking accountability.

“I’ll be the first to admit that the offseason moves we made last year did not lead to immediate productivity on those contracts this year. I have to own that and find a way to be better with those decisions.”

Epstein controls press conferences, not the media. He’s so well prepared for any question that by the time someone wants to ask it, it’s already been answered. There are countless times during this press conference where Epstein has to reiterate what he previously said about the same question. In the first half of 2018, the Cubs led the league in runs scored, OPS and virtually every significant offensive category. They had a total of 40 games where they only scored no runs or one run. In the second half, they had 50 games where they scored two or more runs. And their record in games where they scored two runs was 37-13. They hit more ground balls than other team by a significant margin in the second half (49.5%). There was no denying the offensive failure.

“Part of getting better is facing the problem, and our offense broke.”

He immediately acknowledges the lack of offense, particularly in close games because it was such a glaring weakness. Once he addresses that, the brilliance of Theo Epstein takes over in real time as he gives an in-depth answer into why this might’ve happened. His ability to wield vulnerability allows the media to empathize with the Cubs’ post-World Series complacency.

“There wasn’t a complete sense of urgency every day to win. We have to own this. It’s been a little different since 2016. We have to get back to that.”

Epstein takes his time and is extremely thoughtful about his answers. He acknowledges the issue, gives a possible reason why, and then provides context and comfort on the Cubs organizational outlook going forward. When people talk about the Cubs, they inevitably mention their young players, who have incredible potential: Wilson Contreras, Albert Almora Jr., Ian Happ, Kyle Schwarber and a few others. Epstein admits they haven’t lived up to projections yet and creates his own sense of urgency.

“It’s probably time to stop evaluating in terms of talent and start evaluating in terms of production.”

This shows he’s holding everyone accountable for the performance in 2018. And, perhaps, putting certain people on notice as they head into the 2019 season. Epstein praises his young players, pointing out things they did well during the season and how they are going to improve going forward. He leaves things on a positive note because he knows his players are young and probably watching.

Transparency

Joe Maddon ended the 2018 season managing his team to more wins than any other team in MLB over the last four years. It was confusing why he hadn’t been offered a contract extension going into the last year of his deal. There was a question asked about Epstein and Maddon having personal friction between them, as previously reported.

“We have a terrific working relationship. We don’t agree all the time about baseball issues, and that’s the way it should be. I don’t want a ‘yes man’ as the manager. There should be discord and debate.”

Not only did he not deny their disagreements, but he advocated discourse and the benefits of creative tension. Theo Epstein has stated several times that he likes pushback from people in his front office who make a strong case and advocate for it. Whether it’s an intern or his GM, Epstein welcomes all good ideas, regardless of where they come from. He conveys he’s not a Steinbrennerian executive who dictates lineups to his manager. He’s open to new ideas and wants his working relationships to function with transparency and collaboration.

Honesty

MLB ended its investigation into domestic violence allegations against shortstop Addison Russell and suspended him for 40 regular season games in 2019. MLB’s ruling came down minutes before Epstein addressed the media. He quickly supported MLB’s decision and made pledges that went beyond just the game of baseball.

“Domestic violence is everyone’s problem. We all have an obligation to be part of the solution. It’s my responsibility to find out what we can do to prevent this from ever happening again.”

During the Cubs 2019 spring training press conference, Epstein was faced with another difficult issue involving Joe Ricketts, the father of Cubs Chairman Tom Ricketts, about his leaked Islamophobic and racist emails.

“I’d like to join Tom in stating, unequivocally, that the views expressed in those emails have no place in our organization, in the sport of baseball or in society overall.”

By providing this type of wisdom and honesty, Theo Epstein allows the organization to navigate even the worst possible situations. The Russell and Ricketts stories should be incredibly damaging to an organization. But his leadership qualities are able to not only weather this type of PR storm, but inspire a better tomorrow.

“Diversity is important everywhere, not just because it’s the right thing to do, but because it helps you win. If you’re not diverse, you don’t have the benefit of different backgrounds, histories and perspectives, which is what you need collectively to help you get to the right answer.”

As a listener, you feel better about your ball club, and the world, after hearing him speak.