Wednesday, May 6, 2026

Theo’s Traits I Admire

By: Austin Weaver, @AustinTWeaver

Theo Epstein has broken two of the longest curses in sports. Photo Courtesy of https://bcexcelsior.com/

Like many other students out there, I have aspirations to build a World Series Championship team. Unless you live under a rock, you are aware the Cubs won the World Series for the first time since 1908. You may have also heard that Theo Epstein, the same guy who brought an end to the World Series drought in Boston, was the guy in charge in Chicago.

There are a couple things about Epstein that I admire and try to mimic in my daily life. Obviously, Epstein has been very successful and is in a position that many aspire to reach, but his success isn’t necessarily the biggest attribute I try to model.

Success is great, but it’s the process of getting to success that most intrigues me. While there may be many other pieces to that process, there are three things when it comes to Theo Epstein that I admire the most.

1. Grinded through law school

As a second year law and MBA student, I am constantly overwhelmed with the amount of classwork and information I am supposed to not only consume, but comprehend. Epstein was a full-time employee with the Padres when he enrolled in law school. The time commitment to both his job and schooling is almost incomprehensible, but the fact that he was able to manage it gave me the optimism that I too could take on that challenge.

While I may not be a full-time employee in the University of Iowa’s athletic department, I get up every day ready to attack the challenge that is working in the sports industry and continuing my education.

2. Doesn’t take himself too seriously

The second attribute of Epstein that I believe everyone can learn from is his ability to remain grounded through the pressure and success that comes with his job. From watching a game in the bleachers to eating goat after the Cubs won, and interviewing with a drunk Will Ferrell in the locker room, there are many examples of the type of person that Epstein is.

Bryce Harper got a lot of attention for a hat he wore bearing the slogan, “Make Baseball Fun Again.” It is clear Epstein doesn’t have a problem making sure he is having fun working in baseball. I can only hope I bring as much passion and energy to my career.

I highly recommend this ESPN Article that gives an in-depth look into Epstein and how he approaches his work.

3. Trust in his process

Working for two franchises that were desperate for championships, Epstein, at least publicly, never wavered on his convictions. In trying to break into the sports industry, I often find myself questioning if I am on the right track or if I am doing things the right way. The ability to be steadfast in the plan when the stakes are highest is a trait any good leader needs to have.

If anyone knows Theo, pass along my thanks. Not only for finally bringing my Dad’s Cubs a championship, but for giving me someone to look up to. I hope to not only reach the same level of success, but I hope I can do it in the right way and earn the respect of my peers like Epstein has.

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Apr 29, 2026; Atlanta, Georgia, USA; Detroit Tigers starting pitcher Tarik Skubal (29) throws against the Atlanta Braves in the first inning at Truist Park.

Skubal’s Elbow Surgery Puts Free-Agent Record in Doubt

The star pitcher will likely be out of action for at least two months.
Apr 22, 2026; Saint Paul, Minnesota, USA; Minnesota Wild center Joel Eriksson Ek (14) celebrates his goal with teammates during the second period in game three of the first round of the 2026 Stanley Cup Playoffs against the Dallas Stars at Grand Casino Arena.

Main Street Sports Now One Step Closer to Official Demise

The embattled regional sports network operator reaches another inflection point.
In this photo illustration, a mobile device displays the Kalshi logo while a laptop displays the webpage of the prediction market platform in Copenhagen, Denmark, on February 10, 2026. (Photo by Kristian Tuxen Ladegaard Berg/NurPhoto)

Leagues Weigh In on Future Prediction Market Regulation

Safeguarding integrity and protecting consumers were common themes.
Kalshi's logo is displayed on a smartphone placed on a reflective surface onto which a betting curve is projected in Creteil, France, on March 9, 2026, during a major scandal and a $54 million lawsuit concerning bets related to recent strikes in Iran. (Photo by Samuel Boivin/NurPhoto)NO USE FRANCE

CFTC: ‘Biggest Issue Is Manipulation’ in Sports Event Contracts

Michael Selig says his agency is in talks with “all the major sports leagues.”

Featured Today

Tottenham Spurs

Tottenham Hotspur Is Facing a Billion-Dollar Disaster

A seemingly improbable drop to England’s second tier is a tangible possibility.
Cricket - Indian Premier League - IPL - Final - Royal Challengers Bengaluru v Punjab Kings - Narendra Modi Stadium, Ahmedabad, India - June 4, 2025 Royal Challengers Bengaluru's Rajat Patidar lifts the trophy as he celebrates with teammates after winning the Indian Premier League
May 5, 2026

How Private Equity Fell in Love With Indian Cricket

India’s U.S.-style cricket league has become a private-equity playground.
Kaitlin Oaks (left) from Tampa looks at photos with Layla Abutha from Tampa while attending Thurby at Churchill Downs during the week of Kentucky Derby on Thursday, April 30, 2026.
May 1, 2026

Kentucky Derby Is Courting Gen Z

Churchill Downs is mixing traditional splendor with a youthful atmosphere.
INDIANAPOLIS, INDIANA - MARCH 25: Caitlin Clark of the Indiana Fever sits on the baseline and makes photographs during the Indiana Pacers game against the Los Angeles Lakers at Gainbridge Fieldhouse on March 25, 2026 in Indianapolis, Indiana.
April 22, 2026

Why Athletes Are Moonlighting As Sports Photographers

Athletes are swapping courtside seats for sideline cameras.
Sponsored

Temple Takes Your Sports Career to the Next Level

If you want to break through to the C-Suite , Temple University’s Executive Master of Science in Sport Business can help you up your game and accelerate your career. 
Sponsored

Networking With Purpose

Investing in the Ohio University PMSA unlocks access to one of the largest sports business alumni networks in the world.
Sponsored

University of San Francisco Is Your Ticket to the Game

Rated the No. 1 Sports Management program in California, USF has been a leader in educating industry professionals for more than 30 years.
Sponsored

What Is It Like to Run the Knicks?

Dave Checketts on his time running the Knicks & Jazz, Jordan war stories, and his investment strategy across major sports leagues.
Sponsored

UMass, McCormack Department of Sport Management Introduce Groundbreaking Women in Business Course

UMass’s Mark H. McCormack Department of Sport Management has announced the addition of a Women in Business course launching Spring 2021.
Sponsored

Sacred Heart University Gives Athletes and Students Hands-On Learning Opportunities

Professor Matthew F. Moran is training the industry’s next generation of exercise scientists at Sacred Heart University.
Sponsored

Ohio University PMSA Prepares Sports Professionals For New Normal

Two alumni of the Ohio University Professional Master of Sports Administration explain how they feel prepared for the future of sports.
Sponsored

Temple’s Sports Business Master’s Program Gives a Sports Media Pro Unique Perspective

Temple’s School of Sport, Tourism & Hospitality Management gave Sean Hanrahan the tools to elevate his career even after 30 years in the business.