Jonathan Casillas defied the odds throughout his nine-year NFL career. From going undrafted out of Wisconsin to becoming a two-time Super Bowl champion with the New Orleans Saints and New England Patriots, Casillas’s journey exemplifies perseverance and leadership. The former linebacker, of Puerto Rican and African-American descent, made his mark not just on the field – where he recorded a career-high 96 tackles with the New York Giants in 2016 – but also through his commitment to youth development and community service. Now a media personality and foundation leader, Casillas shares his insights on leadership, preparation, and personal growth in this exclusive interview with Rolling Out’s CEO to CEO series.
[Editor’s note: This is a truncated transcription of a longer video interview. Please see the video for the extended version. Some errors may occur.]
You’re making a difference through your foundation and changing the lives of youth. Why is it important for you to inspire our community despite your success?
Football was great – nine years in the NFL, a couple of Super Bowls as an undrafted player. But that’s not my life’s purpose. The NFL platform helped elevate me to my true calling: helping people and giving back. I know I’m blessed, so I’m always trying to be a blessing to somebody else. These kids are our future – future football players, engineers, pioneers, astronauts. When I talk to kids from areas like where I came from, I let them know that with a plan and consistent work, they can accomplish anything. I’m living proof of that.
What were the key tools you used to sustain a successful nine-year NFL career?
First, being where you’re supposed to be – physically and mentally. In the NFL, we say “Be where your feet are.” When you’re on that field practicing, you have to be locked in, not worrying about anything else. Second, preparation is everything. I learned that from Drew Brees and Tom Brady. Watching these two legends prepare – it was second to none. I learned from literally two of the best players in any sport how to do it day in and day out. Third, dealing with adversity. It’s not if it’s coming – it’s when. You need that tough skin to handle everything from play politics to injuries.
How did you maintain focus despite life’s distractions and temptations?
I kept the main thing the main thing. Some guys can do podcasts while playing, but look at their performance. I chose my time cautiously. Being undrafted, every single year I was fighting for my roster spot. The NFL stands for “not for long.” Sure, I became a captain and was never cut, but I never put myself in situations where I’d miss football because of off-field distractions – whether it was drug testing, clubs, anything. Football had to come first.
What did being a team captain teach you about leadership?
It was deeply humbling. The guys voted me captain even though I wasn’t the best player and didn’t make the most money. That speaks to character. By my later years with the Giants, I’d absorbed everything from the veterans I’d played with. I became that bridge between players and coaches – someone who could communicate complex strategies but also break them down simply. You’ve got to be someone players can turn to for answers but also count on in tough situations. Being captain for my hometown team, the Giants – that topped even the Super Bowl rings. It wasn’t about performance; it was about representing something bigger than myself.
As CEO of your destiny now, what drives you each day?
I love new challenges. The media side is different, especially when you’re talking about a struggling team like the Giants losing 30-7 to the Buccaneers. But I love analyzing the game and staying connected to football. At 37, seven years post-retirement, you have to reinvent yourself. I’m building my brand as a Giants ambassador while exploring new opportunities. Football taught me to embrace challenges – this is just the next chapter.
What advice would you give to young people about leadership and entrepreneurship?
First, master following before leading. As a rookie, I watched Drew Brees command a team meeting – that showed me a whole different level of leadership. Study how great leaders prepare and handle adversity. Second, recognize opportunities everywhere. Speaking on panels, networking, even listening to others – these moments can unlock new chapters in your life. Success isn’t a destination; it’s a journey. Through preparation and determination, you’ll achieve things beyond your imagination. I’ve seen dreams evolve into realities I never expected. That’s the beauty of staying focused and prepared – you create opportunities you couldn’t even envision.
