It’s one of the most critical questions I pose to groups of any and every size I speak to, and often one of the most difficult to bag a consensus answer.

What exactly is leadership?

To the people at “Fortune” magazine, here in 2017, it’s a skill best defined not by a Pope, or a global business tycoon, a Supreme Court Justice or even a former Vice President of the United States.

Leadership is personified by the relatively young man who runs a baseball team. 

And here’s the entire list for your perusal and to begin more than a few good arguments:

Seriously? A BASEBALL GUY as the greatest leader in the world???

Sure. Why not? He’s earned it. More than once. And let’s keep in mind this is about leadership skills, not leading mighty armies, changing political minds or curing diseases.

Think only here about LEADERSHIP.

Upfront, I’ve met and interviewed Theo many times. We became friendly when I was hosting a nightly cable sports show in New England called “Sports Pulse” and I was breaking plenty of local media rules by talking more than just baseball in some rather raucous “1 on 1” interviews. My arrival in New England coincided with the rise of the Boston Red Sox and their improbable run to the World Series, featuring their storybook ALCS win over the NY Yankees and 4 game sweep of the St. Louis Cardinals.

If I sound a little like a fan, it’s because I became one during those years covering the team, their self-proclaimed “band of idiots” on the field, and getting to know the mastermind behind breaking “The Curse of the Bambino”, Theo Epstein.

The man is impressive. From his knowledge of the game to his innate ability to read and relate to people.

Let’s take the line “Well, he’s only a baseball guy!” out of this and focus on leadership skills that can and should be utilized in every business and every life.

Looking at this list objectively, knowing full well that a Cubs Championship likely bent more than a few ears toward being convinced, and with no disrespect meant to any of the other 49 on this list who all would have made excellent choices for top of this list, Epstein does indeed personify what being a leader is all about.

  • STAYING THE COURSE: Theo, and I know he won’t mind if I refer to him by first name, is single minded in his drive and commitment. He allows nothing to sway him nor distract his attention.
  • PATIENCE: To rebuild and change the culture of not one, but two staid organizations that were set in their ways for decades, takes the patience of a Saint. While there are plenty of people who would like him deified for those World Series titles, he got there because he took his time and went about his business of change methodically.
  • A CALM DEMEANOR: Never once did I see the man lose his cool. Talk to people who’ve worked with and for him. He makes his point with a steely gaze and resolve while never displaying explosive anger.
  • TRUST: Theo engenders trust among his people. They know he has their back every second of every day. They also know he will bounce them like rubber balls out of their job if they don’t return that trust. Really good people like to be trusted by their superiors, and the successful ones return that trust ten-fold.
  • TRUTH: Comes right after trust. I’ve never once heard Theo lie to anyone, or for that atter have someone come back and reveal he lied to them. He’s a businessman at the end of the day and I’m certain has told a few in his career, but I could never believe it would be done with malice or bad intent.
  • HE BELIEVES IN SUCCESS: I never once got the feeling he thought of anything but winning. Sure, there were times he likely lost a little faith, but his confidence remained intact. That belief filters down to his entire organization.
  • LEADS BY EXAMPLE: The man has no skeletons in his closet. You won’t see him shooting off his mouth to make a point, tweeting some ridiculous comment that could backfire, dressing anyone down in front of others, treating people with a lack of respect.

And it never hurts to make fun of yourself and just be genuine.

Honestly, I could go on and on with the examples of leadership Theo exemplifies. Hes not perfect, makes his mistakes, owns up to them, and moves on.

These are the qualities of a leader that everyone should seek to copy and bring into their personal and professional lives.

The other 49 on this list are all admirable choices. Every single one has proven what it takes to be a leader. Every single one deserves to be top ranked here. The best thing about lists such as this? It opens up a conversation about a topic we should ALL be talking about.


You may never win a World Series, but reaching the pinnacle of success in your field is possible by understanding what it means to be a real and honest leader.

Learn that and it’s a home run every single time.