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Volume 23 No. 13
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Forum: Impressions of Derek Jeter as CEO

A year ago in a conference room in New York City, a group of well-regarded sports business executives were finishing up a meeting, and the conversation turned to Derek Jeter’s early, tumultuous days as owner of the Miami Marlins. “Baseball picked the wrong ownership group,” one person said, arguing that the Jeter/Bruce Sherman group was not as qualified as a competing group led by Miami business executive Jorge Mas. I listened to the criticism of the former Yankees shortstop, which added to the heavy media scrutiny Jeter already had received from local and national baseball writers.

But my view was that Jeter had won baseball’s blessing and the bid, and earned the right to do what he felt was needed to turn the franchise around. He made controversial changes — such as trading away star players and dismissing longtime advisers and “faces” of the franchise like Jeff Conine  and Jack McKeon — and people severely criticized him for being tone deaf and ill-prepared. But I wanted to be patient and give him the benefit of the doubt as he tried trying to change the narrative around a troubled franchise. 

Now, I’m beginning to have doubts about the efficacy of his leadership.  The quick parting with well-respected business executive Chip Bowers after just 14 months indicated to me that Jeter may be inheriting the traits of some of the least successful owners I’ve witnessed in sports: impatience and an inability to trust different points of view. 

Bowers was brought in from the Golden State Warriors, where he served six years as CMO, after a long stint with the Orlando Magic. He has learned under the watchful eye of owners such as Joe Lacob and Peter Guber, as well as executives Rick Welts, Steve Griggs and Alex Martins. He was hired by Jeter as president of business operations in March 2018 after an extensive search. 

It was understood this was going to be a long, slow turnaround. Many remain skeptical of the South Florida market, and it was badly damaged by previous ownership.  People early on seemed to be on the same page that this was going to be a grind and take time, and the key was to get all the staff — from ownership on down — to believe and buy into the process. There were going to be some tough, unpopular decisions.

But now, just over a year later, Bowers is gone. I’m sure that both sides wish they had handled their relationship differently.  Bowers has been in the business for 24 years. He has strong points of view about how an operation should run. Jeter is a future hall of famer, and not many around him have told him no or pushed back on what he wants. I get that. But confident, secure ownership must — and generally can — get past that. We all know that owners are opinionated. They believe they are the smartest people in the room and have the answers. They’ve been very successful, and always want to be heard. But the successful and effective ownership I’ve witnessed can discuss and debate, but in the end will listen to their people, the experts with experience they’ve hired to operate their business. 

Where ownership can get off the rails is by micro-managing, sweating the small stuff and weighing in on every single decision. Jeter can’t fall into that trap. He must be the outward-facing leader in the community and build relationships while also showing that he’s in for the long haul, and that it’s going to be a process. He has to understand all of the various constituencies — both inside and outside the organization. While Jeter was  incredibly successful for a tremendous organization for 20 years, it doesn’t mean he’s a fully formed CEO. He can’t insulate himself or surround himself with those who won’t challenge him and with little experience in  the complexities of team operations. 

Shortly after parting ways with Bowers, Jeter said he was not happy with the performance of the franchise “but we’re working hard on gaining the trust of our fan base.” Working hard has never been a problem for Jeter, and no one has questioned his work ethic in South Florida. But he must be open to different points of view, to let experienced voices help inform his decision-making, become aligned with them and let them do their jobs. Only then, potentially, can the Marlins begin to turn things around.


First Look podcast, with issues Abe is watching this week, at the 15:10 mark:

Abraham Madkour can be reached at