Beyond the Legal X’s and O’s

With a passion for technology and social media, one of the youngest general counsel in the NFL is taking her expertise past the legal realm

A perturbed silence fell over thousands at Jacksonville Municipal Stadium as Morten Andersen lined up for the thirty-yard field goal attempt. Here was a player who, as kicker for the Atlanta Falcons, had made fifty-nine consecutive field goals from less than thirty yards away. Looking to add number sixty to his streak in 1996, Andersen and the Falcons hoped to eliminate the Jacksonville Jaguars—one of the youngest NFL franchises that was only in its second season at that point—from playoff contention.

Less than a few seconds later, that silence and looming dread was quickly replaced by the cheers of thousands, as what would later be called Morten’s Miss sailed wide left by one yard. The following week, the Jaguars won the Wild Card game in Buffalo, only to follow up that impeccable run by pulling off one of the major upsets in NFL history by defeating John Elway’s Denver Broncos in the Divisional Round. Upon the return home to Jacksonville, the Jaguars were greeted by an estimated 40,000 fans gathered at the stadium.

It wasn’t only that 1996 season that was impressive, but after establishing the franchise the year before, the team would make the playoffs four straight years from 1996 to 1999, a feat that has perplexed many as to how a team in a market as small as Jacksonville was able to accomplish this success so quickly. They, of course, had a few factors in their favor: future Super Bowl-winning head coach Tom Coughlin (now executive vice president of football operations for the Jaguars), a Pro Bowl quarterback in Mark Brunell, and a dynamic receiving duo in Jimmy Smith and Keenan McCardell. But they also had a youthful energy that could ride a tangible excitement throughout Florida’s First Coast. That innovative spirit has been a tradition in the greater Jacksonville area ever since.

During those initial years of the franchise in the late 1990s, Cassie Sadowitz wasn’t considering a career in law. In fact, she wasn’t even in college yet. But now, as the general counsel for the Jacksonville Jaguars, she is bringing that same youthful energy to the front office to accumulate multiple wins off the field. These victories may not be showing up in an almanac, but they are making waves throughout the NFL.

“Never in a million years did I ever think that I would someday end up as one of the youngest general counsel in the NFL,” Sadowitz says.

In comparison to other general counsel, and just like the Jaguars’ playoff run in 1996, Sadowitz took more of the unconventional route to the NFL. With a passion for social media, technology, marketing, and branding, Sadowitz is bringing a new playbook to the Jaguars that aligns legal with all aspects of the organization. During her second year of law school, Sadowitz reached out to David Cohen, who was the director of legal at the time for the MLB’s Los Angeles Angels. With guidance from Cohen, Sadowitz earned an internship with the team and learned the ropes about being an in-house counsel for a sports team. “At the time, I didn’t realize exactly how my foundation in tech would translate into the sports world. But it turns out that the two are inextricably linked,” Sadowitz recalls.

Upon graduation from law school, Sadowitz accepted a legal role with the NFL’s Tampa Bay Buccaneers. She spent just shy of two seasons with the Buccaneers before moving north to join the Jacksonville Jaguars in November 2014. Now Sadowitz, along with the team’s chief legal officer, manage all legal aspects of the business. This includes transactions, litigation strategy, compliance, and working with each department to help drive revenue while minimizing exposure. She also supports different areas of sponsorship, marketing, hospitality, ticket sales, and employee relations.

“I find that the legal department is really the pulse of the organization that touches all aspects of the business,” she says. “What I’ve found is that to be effective in this role, no matter what team you’re with, you have to get to know your colleagues, the operations, and really understand the competing priorities of each department. That’s very important to me.”

It was an eye for social media and branding that originally caught the eye of Cohen and helped Sadowitz spearhead her legal career. To this day, Sadowitz is bringing the same strategy to the Jaguars. She works directly with marketing and other sectors of the organization, whether it’s a matter of drafting promotion rules, protecting intellectual property, or providing counsel on ad copy.

“A sports brand is typically successful when it can capture the hearts and the minds of its fans, its sponsors, and serve as a symbol that also helps drive incremental revenue,” she says. “We work with marketing on a daily basis, and we’re constantly trying to come up with new, unique ways to reach our audience. As a younger team in the NFL, we are up against larger markets and franchises that have been around for decades, which makes for exciting competition off the field.”

It’s also promoting an individual brand, particularly in the legal realm, that helps one stand out. Doing so for Sadowitz was instrumental when seeking her first role with the Angels, and it’s something she inspires fellow general counsel to do. “Too often, attorneys are stuck in that very black and white mentality,” she says. “If you have an understanding of how competitive the legal industry is, especially sports law, you can think creatively of ways to present yourself with an unconventional application and making yourself stand out. I think that is especially true for me, given my story and my journey.”

Over the years, the popularity of the NFL has skyrocketed. Right alongside this exponential growth has been a surge in social media. For the Jaguars, social media paves the way for the organization and players to connect with the community and fans. It also opens up more opportunities for conversations, which can be instrumental in helping direct business strategies.

“It’s critically important to be able to reach the younger generations,” Sadowitz explains. “Social media teaches us a lot about the wants, needs, and desires of our fans and audience at large. I think at the end of the day, interaction is key. The days of one-way story telling are long behind us. It’s now about fostering a dialogue between an invested fan base and all the stakeholders involved with the brand—players, employees, sponsors—and the ability to create an ecosystem, where everyone can come together and share the common affinity for the team.”

Social media has also been imperative in allowing the Jacksonville Jaguars to connect with fans internationally. Since 2013, the Jaguars have played a game each season in London. Social media allows the team to interact with its UK fan base, affectionately called the Union Jax. Along with interacting with fans, social media enables the organization to connect with the community, including releasing a video called Lifework that allows fans to experience the behind the scenes of what it’s like working for the Jaguars. Sadowitz and the Jaguars have also worked with several sponsors, including Bud Light on a hashtag campaign, Firehouse Subs on game day-related promotions, and Mellow Mushroom on Instagram contests.

“Many legal teams out there still don’t really understand the power of social media and oftentimes don’t want to launch dynamic promotions, because it can be seen as a risky, unchartered area of the law,” Sadowitz explains. “But from our perspective, we never want to be known as the lawyers who say no and shut down ideas. We always want to be open to innovative ways to enhance our brand and brainstorm the best pathway in an evolving area of the law.”

But Sadowitz also notes that the trend is changing, as more general counsel are becoming aware of social media and its impact on the business of an organization. She says that having an in-house legal team that’s privy to the evolving legal landscape can proactively help alleviate risk when it comes to crafting high-profile social media activations.

“The platforms are changing. The audiences are changing. Being able to stay in tune with what those developments are and the wants of our audience make things a lot easier during the execution phase,” she says.

That same tangible excitement was paramount in the late 1990s and is coming back again with several new initiatives from the Jaguars, including a massive stadium improvement project with updates to certain premium spaces, construction of an amphitheater known as Daily’s Place, and the team’s covered flex field. Serving as a multi-use facility being built adjacent to EverBank Field, Daily’s Place and the covered flex field will bring an entertainment district to Jacksonville. Even though the city is a smaller market, its innovation and youthful spirit can rival any NFL franchise. And with Sadowitz on the executive team, that excitement will echo throughout the organization and the city.

“We’re a relatively young team in the NFL, and all these initiatives that we’re undertaking—the improvements to the stadium, the covered flex field, the amphitheater, even just the technology that’s been introduced in recent years—all of those things make for a stellar fan experience. That’s really what Jacksonville needs. We want this to be a premier entertainment destination,” Sadowitz says.

Serving the Community

Even with being one of the youngest NFL franchises, the Jacksonville Jaguars organization has a long history of giving back to the community. That tradition expanded further in 2016 with the launch of the Jax MVP program.

The Jaguars Foundation, together with US Assure, created this program to provide an opportunity for a select group of local, emerging business leaders to engage in professional development curricula and also give back to the community. The organization raises funds for various causes including education, women’s health, military and veterans, as well as family programs. This is just one example, though, of the numerous ways the Jaguars give back.

“It’s incredibly rewarding to be able to launch programs that leverage the team, business relationships, and resources to help give back to the community,” Sadowitz says.