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“Without the players, there is no sport. They are the special sauce and what make the sport exciting. When I watch a game and see pure joy on athletes’ faces as they do something really special in a big moment -- show that emotion -- that’s what I remember."

Shawn McDonald

Vice President, Business and Legal Affairs

Q & A with Shawn McDonald

Shawn McDonald

Vice President, Business and Legal Affairs

On his early education and college background

Neither of my parents graduated high school, and I mention that because education was always very important to me and it’s something I’m very proud of given where I came from.

 

I went to Cornell for undergrad where I had wonderful professors who pushed me hard - they expected a lot of me, and so I expected a lot of myself.  I played for Cornell Football for a couple of years, which I enjoyed.

 

After Cornell I went straight to Harvard Law School.  Harvard Law was a goal of mine from when I was 12 years old. I was very proud when I received the acceptance letter as I knew how much my father had sacrificed to give me that opportunity.  Graduation was one of the few times in my life I saw my dad cry tears of joy.  

On breaking into the sports/ athletics industry

When I started off as a lawyer at Cravath, Swaine & Moore, I immediately tried to network within the sports industry to meet with any and everyone to hopefully get an opportunity to break through. It took me 11 years to get that breakthrough, but I think it is important to be persistent.

 

When the opportunity presented itself to work for an incredible company like Nike, I ran – I didn’t walk. I finally had the chance to break into sports and broaden my skill set and my experience beyond legal. My role there was Business Affairs Director for North America Sports Marketing. I was on the business side, though they wanted a lawyer in that role because I negotiated their biggest deals with the MLBPA, NFLPA, MLB, NFL and NCAA.  After the business terms were agreed to I managed the process at the legal department as we finalized the longform.  Once the longform was signed I owned the contracts both internally and externally. I explained to the business what our rights were, helped them think strategically how to use it, and I was one of a handful of people who was partner facing as it related to my deals.

 

It was in that capacity where I met Evan [Kaplan]. I met him at Nike and negotiated a couple of deals with him and got to know him personally and his family. We formed a friendship, but also a great mutual respect for each other. So, when this opportunity presented itself, it felt like the stars were aligned.

On his baseball fandom

I’m a massive baseball fan, all the way down to Single-A. Some of my favorite players I’ve been following since they were 16 or 17 years old.  I enjoy watching a player progress through the minors and get their shot in the big leagues.

 

When I was five, I picked every archrival team against my dad in every sport – and I love my dad, but it just made sports viewing at the house more interesting. Even though I grew up in New York City, I’m a diehard Red Sox fan and have been my whole life.

On his new role with the MLBPA

My role is going to be about 70 percent legal and 30 percent business, and I’ll be assisting on all matters business and legal for Evan and collaborating with Heather, Rob and the rest of the team. Two particular areas of focus for me will be our relationship with OneTeam Partners and negotiations with MLB. I’m really excited to be a part of the team and roll up my sleeves.

On working on the Players’ behalf

With Nike, the focus was empowering athletes. So yes, I negotiated deals with various organizations but at the core, at Nike’s mission, is to service the athlete. MLBPA and MLBPI obviously is, in my opinion, the strongest union in sports and one of the strongest unions in the country.

 

Without the players, there is no sport. They are the special sauce and what make the sport exciting. When I watch a game and see pure joy on athletes’ faces as they do something really special in a big moment -- show that emotion -- that’s what I remember. Being an advocate for the players is something that very much excited me.  I also think it was very important for the folks I interviewed with to know that empowering the athlete was something that would be a motivating factor for me as that is a core value of the union.

 

I am coming from an organization that was focused on storytelling from a player’s perspective and trying to be advocates for them and I believe it will be a seamless transition for me to come over to this side.  I think my experience on the business side, including understanding the metrics of how we can market the players and amplify their voices will be an asset to the team.

On the future of baseball

I love that we’re starting to see some players on teams show more and more emotion.   When the player is the focus, the game thrives.   Given all the great talent, young and veterans, I think the game is in good hands now and moving forward.

On the lessons his father has taught him

My father never let me win anything as a child, ever.  He wanted me to know when I won, I truly won.  He taught me chess at eight years old, and I didn’t beat him until I was 16. To this day, I remember the day that I beat him, and I remember how I felt. My father instilled in me a work ethic, pushed me hard and made personal sacrifices so that I would have opportunities. I have profound respect for those sacrifices and have worked very hard to take advantage of the opportunities I have had in my life. That drive is still with me today and is a big part of the fire within me that I will bring to the union. 

On his hobbies

My most prized degree is from a Scratch DJ Academy.  It was there that learned to DJ right out of law school.  I still have my turntables and thousands of vinyls, and I really enjoy it. I love mixing in hip-hop, R&B and soul.

 

I also love sports. My wife when we were dating said, ‘I understood that you liked sports, maybe I even understood that you loved sports, but I didn’t understand that during the quarantine you’d be setting an alarm to watch Korean baseball at three in the morning.’

On his advice to others wanting a career in sports

To folks who want to break into sports, I’d reiterate the advice that was given to me when I was younger. As a native New Yorker, I once told someone essentially that I wanted to be in sports but I wanted to be in New York. He told me, ‘Then you’re telling me you’re not serious about wanting a career in sports, because if you’re serious you’ll be willing to move anywhere and do anything to break in and prove yourself, and then go where the opportunity presents itself.’ That was tough to hear as a 24-year-old, but I did take it to heart, and I put my money where my mouth is and I ultimately took an opportunity in Portland [Oregon].

 

I would say to people who want a career in sports, if you’re not willing to move anywhere at any time and do whatever to break in, trust me there are tens of thousands of other people that are and you’re just not going to get the chance. Be willing to get out of your comfort zone if this is a passion of yours.