A dream of mine dating back to the time I was in middle school was to work in the business side of baseball, ideally for a team or the league office. As I got older, I realized the part of the business that intersects most closely with professional athletes is labor and employment law, since athletes are the labor and the product of the leagues and the teams. This realization is what led me to pursuing Cornell’s Industrial and Labor Relations (ILR) school and continuing onto law school at the University of Buffalo.
As I researched executives who worked in the sports law field, I came across a young, highly successful attorney who followed a similar path that I would like to pursue, Jessica Villanella. Jessica is the Vice President of Employee Relations & Co-General Counsel for the New York Mets. Her background in labor and employment law helped lead her to where she is with the Mets today.
Jessica had an extremely unique path into the business of sports, being the daughter of a former NBA coach. Jessica was born in Switzerland and moved 18 times as a kid. From the beginning, professional sports was her family business and she knew she wanted to work in sports, but not in what capacity. Jessica was a Division I athlete, playing basketball at Stony Brook University, and she expressed that at that time playing basketball was her number one priority. In her junior year, she said she realized she needed to think about life after basketball. This was when she realized law school felt like a profession that spoke to her, but she had no lawyers in her life and she lacked perspective on the legal profession other than what was portrayed on TV. She felt that it was the right path for her, but she did not want to jump right into law school without being 100% sure, given the fact it is a major investment.
Following her time at Stony Brook, Jessica decided to pursue a paralegal position with a law firm in Chicago. She chose Chicago because at the time her father was coaching with the Chicago Bulls. Working as a litigation paralegal solidified her decision to pursue law school. When applying to law school, Jessica wanted to go to school in the Midwest, specifically Marquette University, which has a very strong sports law program and was where her dad went to college. Although this was her initial plan, life changed for her and she knew she wanted to go back to New York City for law school. She emphasized how thankful she was to have made that choice because “it’s the market you want to be in if you want to work in sports.”
This led her to taking a different job as a paralegal in NYC with an in-house firm that represented the Newhouse family. At the time the firm she was working for was doing substantial work in the entertainment sector, specifically for Conde Nast Publications, Bright House Networks and different newspapers throughout the country that belonged to the Newhouse family. During her time there, Jessica specifically did labor and employment work in the entertainment sector. This experience was helpful in guiding her to an area of law she enjoyed. She was adamant about continuing to work, so she worked as a paralegal during the day and attended law school at Seton Hall University at night. A combination of the long commute from Manhattan to New Jersey to attend classes at night, paired with Jessica receiving strong grades in her first year of law school, led her to transferring to Fordham Law School. She continued working for the firm she was with and attended night classes to complete her degree. She did not participate in any clubs, law review, or journals in school, she said “I was only going to get the degree.” She planned to start her career with the firm she was working for.
In her final year of law school, someone brought to her attention that the NHL was looking for a labor and employment intern. Since sports was her end goal, she applied for the internship and ultimately was offered it by the NHL. When she went to the Commissioner’s office she had the privilege of meeting general counsels and the Commissioner himself, but she knew she needed full-time employment. Because of this, she turned down the internship, but the league was unwilling to let her go. Through advocating for herself and explaining she was looking for a full-time job, she got the NHL league office to offer her just that. A piece of advice that Jessica shared with me during our talk that will stick with me was, “if they want you, then it is the right time to ask for what you want.” Jessica did just that, and ended up taking the job with the NHL.
Her time at the NHL was extremely eventful as she started her job with the league during collective bargaining negotiations, which ultimately led to a lockout when the league lost half a season. Although it was a dark time for the sport, Jessica gained invaluable first-hand experience at the bargaining table and working around the clock. She explained that every hour outside of law school was dedicated to the league and that her experience there was one of the most extreme times for any sports league. She explained how unique it was to see what was really happening from the inside, as opposed to media reactions and outside voice spreading speculation on the matter. After giving tremendous sweat equity to the NHL league office and graduating from Fordham Law School, her mentor at the NHL, Jessica Berman, approached her with career advice. Her advice was that gaining firm experience would be the best thing for Jessica’s career. At this point in our conversation, Jessica emphasized that “the sports community is a super small world and to make sure you don’t burn any bridges.” Between Ms. Berman and the attorneys Jessica had previously worked with, she was offered a few interviews with law firms in New York City.
At this point in time, Jessica had been practicing as a labor and employment paralegal/law clerk for nearly seven years. Ultimately, she interviewed with Jackson Lewis, P.C. and accepted a position with the nationally recognized labor and employment firm. Her initial plan was to work 3-5 years as an associate for Jackson Lewis and gain general firm experience, but after just one year Jessica Berman called her to tell her that the New York Mets were seeking an entry level counsel with labor and employment experience. Ms. Berman made the call to the Mets, and this led to an expedited interview process where Jessica was soon offered the job. She knew she had to be thoughtful and careful with Jackson Lewis, so she made sure to sit with the managing partner to discuss this opportunity, and when she did he showed nothing but excitement for her and told her to pursue the opportunity. Jessica started with the Mets in 2014 and was promoted to General Counsel in 2021.
Jessica’s path is very inspirational, but so was her advice to aspiring sports attorneys. She started by first saying networking and making as many connections as you can is extremely important. She says when they are hiring she gets thousands of resumes and when you are a referral or a previous intern, it separates you from being just another resume. Going off of making connections, she emphasized that you must build on the relationships so that the people actually know you and can speak genuinely of your character or work they have seen you do. Along with that she said to be as involved you can with the industry related groups at your school that you are interested in. Having things like groups, internships, or competitions that are industry specific will help an aspiring sports lawyer stand out. Also, in terms of positioning yourself, she said be sure to do well in law school and gain experience in areas you know would translate to the job you aspire to get. One of the best pieces of advice she gave me during this segment of our talk was “When you pick a job you can reach and challenge yourself, but in law be careful not to put yourself in a position to fail because that can be detrimental. Be thoughtful and careful when accepting an opportunity.”
Towards the end of our interview, I asked Jessica what she loves outside of baseball. Without hesitation, she said she loved being a mom. She has two kids, a one year old and a three year old, whom she loves spending time with. She also said she loved to travel (which she noted is very contradictory when having two little kids), but since she moved around the country her whole life she knows how much beauty there is in the world and loves the opportunity to go out and see it.
Afterward, we discussed the work-life balance as a team executive and to my surprise she was thrilled with how much it is valued in the New York Mets organization. She said it was a major focus of the Mets to diversify workplace and sport and to be able to accommodate working parents. She noted that flexibility is key and that the pandemic showed us how possible it is. She said the organization is very comfortable with its employees working remotely, and that she herself enjoyed the opportunity to work remotely so that she could spend time with her kids. She noted that it starts from the top and that the Mets organization highly values this flexibility and everyone gets the opportunity to do what is best for them to give their 100% at work.
When I asked her what the most rewarding part of her job was, I was anticipating the World Series appearance the Mets made in 2015, but she gave me a much more thoughtful response. She told me the most rewarding part of her job was when employees she works with say thank you for something and that it made a difference in their lives. For Jessica, she gains professional fulfilment from making a difference in her colleagues’ lives, helping them enjoy their jobs, and giving them the opportunity to live their lives outside of work a little easier. I then asked what the most challenging part of her job was, and to no surprise she said it was working through the pandemic. From the pandemic shortened season to executive change at the Mets, the pandemic provided many challenges for her.
I then asked if there was anything about her job that people unfamiliar with the responsibilities of a sports team’s general counsel might not know. Her answer to this was the limited interaction there is with players. Many people are under the notion that if you work for a team you work closely with the athletes, but Jessica said that is a minimal part of her job. She wanted people who might aspire to be in-house counsel for a team to know that going in, and to not be deterred when they are not interacting with players as a daily part of their job.
Finally, I asked her if there was anything else she wanted to share that I had not asked about. She told me she was extremely proud to be a female executive in baseball and that it is part of a small community so that she takes great pride in it. She also noted that she was honored to be in the presence of the other incredible women who are doing it.
Jessica’s story was inspirational and encouraging to me as an aspiring sports attorney. Our entire conversation was incredibly insightful and speaks to the work ethic and drive that Jessica has had her entire career and that has propelled her to be where she is today. I am incredibly thankful that someone as high up in the sports world as Jessica Villanella, with so many responsibilities, was willing to take the time to talk and share advice with me.