Brennan Whitley knew from a young age he wanted to work in sports. Throughout high school and college, he seized opportunities to volunteer at the City of Palms Classic basketball tournament and to intern for organizations like the Fort Myers Miracle (now the Mighty Mussels), Tampa Bay Rays and Florida Gulf Coast University athletic department.
He was able to parlay his last internship, with the Boston Red Sox’s spring training operations in Fort Myers, into a full-time job — thanks to an assist from boss and mentor Katie Haas. She essentially created his role in Florida business operations for the Red Sox in order to keep him as part of the team.
'It’s long hours and little pay, and you’re preached that from day one in college. If you come in here thinking you’ll be the GM of the Red Sox within three years, you’ve got something else coming for you.' Brennan Whitley
“She showed me the ropes and she believed in me,” says Whitley. “She was someone who didn’t micromanage. She didn’t constantly look over your shoulder, but she was there for any support you needed. She was there whenever you had a question, but she trusted us to get our jobs done.”
He watched her work with Lee County during construction of JetBlue Park and navigate the sports world as a woman in leadership, and her example and guidance has been instrumental in his career. “It allowed me to grow into who I am today,” says Whitley.
Now he’s helping to inspire the next generation in sports management, whether it’s hiring and working with the Red Sox’s spring training interns or speaking with FGCU students interested in a career like his. “I give a tour of our facility every year to an FGCU sports concentration class and give a tough love speech on what it takes to get into sports,” he says. “The initiative is the biggest thing.”
Whitley loves that no two days are the same in his job. “Something different comes down the pipeline every day,” he says.
That requires an ability to shift and adapt. “Sports is a fast-paced environment, and it’s not for everyone,” he says. “It’s long hours and little pay, and you’re preached that from day one in college. If you come in here thinking you’ll be the GM of the Red Sox within three years, you’ve got something else coming for you.”
Name: Brennan Whitley
City of Residence: Fort Myers
Employer: Boston Red Sox
Title: Senior Manager, Florida Business Operations
Birthplace: Fort Myers
Years in the area: 33
Marital Status/Children: Married
Alma Mater/Degree: University of Tampa, Sport Management
What community group or organization are you most involved with? Boys and Girls Club of Lee County and City of Palms Classic basketball tournament
What's the weirdest job you've ever had? Selling waffles at a minor league baseball game for Billy Donovan Night as he was "waffling" between coaching at the University of Florida and going to the NBA
What's your top tip for being productive? Stop procrastinating! Set time for you, and make sure you take care of yourself first. If you are not in the right place mentally, everything will seem like a 99 mph fastball up and in.
If you could have a side hustle, what would it be? Event consulting
What's your favorite off-hours activity? Golf
Have you gone to the movies in 2021? If yes, what did you see? Nope, but love Outer Banks on Netflix!
What's the top item on your bucket list? Playing the top 100 golf courses in the world!
What's your favorite podcast? Section 10 Podcast
Where is your happy place? On a beach in the islands with my wife and dogs!
Describe yourself in three words: Driven, trustworthy, dependable.
Who is your mentor for your career and why? My former boss, Katie Haas. She gave me my first opportunity with the Red Sox and taught me what it takes to be successful in a MLB Front Office.
What are the biggest lessons you have learned from your mentor? Don't let others get in the way of progression! Break through those barriers and lead by example. Talk to your employees and set the example for how they should approach customer service. Learn people's names, it's not easy with a staff of over 200, but call them by name whenever possible.