By Joe Bosso, Portraits by Scott McDermott

Michael Strahan admits that he has a lot of cars, but he isn’t exactly sure how many he owns. Surveying the enviable fleet of cool, classy rides (special emphasis on Mercedes and Porsche) that are stacked on hydraulic lifts inside his Hackensack, New Jersey, warehouse, the former NFL superstar turned media titan suggests that the size of the group is always in flux.

“Cars seem to come and go,” he says. “I’ve got some that are being worked on, and a few are out being sold. What happens is, I’ll get something that I enjoy for a while, but if I stop using it—I’ll sell it. Or I’ll get multiples of certain cars and then I’ll sell one. Some stick around longer than others.”

The auto room comprises one half of the warehouse; the second portion is what Strahan affectionately calls “Strayland,” his deluxe getaway spot/man cave complete with cozy couches, a full bar, a refrigerator-sized humidor, a widescreen TV, a golf simulator and other big-kid toys and goodies. Although his high-profile cohosting duties on Good Morning America and its third-hour series Strahan and Sara keeps him in New York City for much of the week (to make those 5 AM wake-up calls, he maintains an apartment on Manhattan’s West Side), he relishes any opportunity he can grab to kick back in his award-and-trophy festooned funhouse.

“This is the best place when I need to decompress,” he says. “It’s my secret spot to get away from it all and relax from the city. Depending on my schedule, I’ll come here once or twice a week. Last week I was here five times. My brother will come by, and we’ll hang out. Other times, I’ll just drive out by myself. I’ll sit here and watch TV, smoke a cigar. Sometimes it helps just to do nothing.”

“Doing nothing” sounds antithetical to how Strahan has lived much of his adult life. There is, of course, his celebrated career as a defensive end: He spent his entire 15 years in the NFL with the New York Giants, setting a record for the most sacks in one season (2001), and helping the team score a Super Bowl victory over the New England Patriots in his final year as a player in 2007. Since then, he’s become a dominant presence on the airwaves. In addition to both GMA shows, he’s a football analyst on Fox NFL Sundays, and his production company, SMAC Entertainment, has been responsible for a number of programs such as The $100,000 Pyramid (which he hosts), the Nickelodeon Kids’ Choice Sports Awards and a reboot of The Joker’s Wild (hosted by Snoop Dog), among others. He’s even tried his hand at acting, appearing as a main character on the Fox sitcom Brothers, as well as turning in a memorable cameo in the film Magic Mike XXL.

All of which begs the question: Is there anything Strahan can’t do?

He laughs and says, “I’m bad at a lot of things, but I won’t admit it.” Pressed for specifics, he allows, “Well, I can’t play an instrument. Guitar, drums—I’m horrible at music. I did take some piano lessons. At first I picked it up OK, but then I grew frustrated. It’s something I would try to do again if I had the time.”

Musical failings aside, the inveterate multi-tasker and entrepreneur has found success in a number of other areas—like fashion: In 2015, Strahan launched his line of men’s formal wear, Collection by Michael Strahan, available at JCPenney. Robust sales allowed him to extend his reach into athleisure clothing (MSX by Michael Strahan) and even a luggage line.

He sits back and waxes philosophical: “If there’s a reason why I’ve been successful, I think it’s because of an authenticity factor. What I put out there is who I am. I’m not selling you something or trying to make you buy something I wouldn’t wear myself. Same goes for the rest of my career. I’m myself at all times, and so you’re not surprised at what you get. Whatever you do, be authentic. If you can do that, good things will follow.”

The Interview

Let’s talk cigars. What was the first cigar that really did it for you?

The first cigar that gave me an incredible feeling was a Cohiba. My friend Harvey Sanders gave me one, and it was like, “Whoa! This is a good cigar.” Ever since then, I’ve been a cigar guy. I have humidors filled with cigars, and I love to share them. It’s a great social thing. My buddies will come out and we’ll smoke cigars. Sometimes I’ll come here by myself, and I’ll smoke a cigar and go over notes; sometimes I’ll just look up at the trees and enjoy the peace. I smoke a few days a week, mostly on weekends. Or when I’m golfing—it’s funny how a cigar will turn a bad game around.

Do you experiment with brands, or do you have dedicated favorites?

I experiment a lot. You try new things and make discoveries. I love Gurkhas and Padrons – they’ve got a nice, easy pull. I’ve got Olivas in the humidor. Friends give me cigars to try out. One of my friends gave me this box of Davidoffs – Year of the Pig. I tried ‘em out, and they’re awesome cigars.

I understand you’re also a big tequila fan.

Look at my wall, you know? [Laughs] I never liked beer, which is funny because I grew up in Germany. Plus, the beer belly thing scared me. When I was younger, I drank Sambuca, and then I got a little soft with Malibu Sea Breezes. My buddies made a little fun of me with that.

Want more? Subscribe to Cigar & Spirits Magazine!