FRESH FROM A Wednesday taping of Good Morning America, Michael Strahan heads to downtown Manhattan cradling two leather watch cases in the crook of his left arm, like he’s just recovered a fumble. Embossed with his initials, MAS, each holds four watches worth nearly $1 million in total. “I just grabbed a bunch,” Strahan says of his collection, which includes some 40 watches, including Audemars Piguet, De Bethune, Hublot and plenty of Rolex Daytonas.

“A Daytona was my first big watch purchase when I came to the NFL. If it says Rolex Daytona on it, I have it,” he says. “I think it’s like me: durable, sustainable and versatile.”

At 53, Strahan has certainly stood the test of time. He spent 15 years (1993–2007) as a defensive end for the New York Giants, becoming one of the most dominant pass rushers in history. In 2014, seven years after helping the Giants win Super Bowl XLII, he was inducted into the Pro Football Hall of Fame. Going pro was never a given for Strahan, who was born in Houston but grew up in Germany, where his father was a major in the Army’s 82nd Airborne Division. “I was hoping just to have a job when I got out of college,” he says of his years at Texas Southern University, where he followed in his uncle’s cleats as a star defensive end.

That mentality has clearly stayed with him since he hung up his helmet in 2008. He joined the Fox NFL Sunday team immediately after, and in 2012, he beat out an all-star roster of talent to become cohost of Live! with Kelly Ripa. Four years later, he landed his current role as a cohost of Good Morning America and added a side hustle as host of The $100,000 Pyramid. All told, Forbes estimates that his TV work earns Stra­han at least $20 million a year, considerably more than the $6.9 million he averaged on the field for his final ten seasons with the Giants.

“I never expected my career to be what it has been, or continues to be, at all,” Strahan says, wearing a $76,000 “John Mayer” Rolex. “I always liked nice things, but I never knew I’d be able to afford a lot of nice things. It’s given me an appreciation for what I have because I know what it’s like to always want something and not be able to have it.”

In addition to his watch collection—which Forbes estimates is worth some $2 million—Strahan also collects cars and spirits, but he says watches are “like artworks” that also measure success. “If you’ve ever gone to a factory to see how a watch is built, you see how much craftsmanship and precision goes into it. There’s so much thought that goes into making these things that we just throw on our wrist.”

For instance, when Jeff Bezos’ Blue Origin invited Stra­han to travel to space in 2021, he wore two timepieces with celestial significance: a $44,600 Rolex GMT-Master II with a meteorite dial and a $125,000 Star Trek–inspired De Beth­une watch. “Someone might say, ‘Well, I have this electronic watch, it keeps the same time,’ ” he says. “Yeah, it keeps the same time—but it doesn’t have any kind of personality to it. And to me, a watch is about personality.”

He applies that philosophy to giving watches as well. A few years ago, he presented Constance Schwartz-Morini, cofounder of his talent and production company, Smac Entertainment, with a Rolex Oyster Perpetual with a yellow dial, calling her “the sunshine in my life.”

Schwartz-Morini met Strahan while working for the NFL’s marketing team. She then moved into talent management, representing Snoop Dogg before getting into business with Strahan. Founded in 2011, Smac produ­ces content and mana­ges talent such as Wiz Khalifa, Deion Sanders and Houston Texans wide receiver Stefon Diggs. Now the CEO of Smac, Schwartz-Morini says she tries to impose on Strahan’s time only when necessary. “He’s committed to every single thing that he’s attached to,” she says. “Or else he won’t do it.”

Last year, Strahan took on a new challenge—the world of investing—with billionaire Marc Lasry, cofounder of the $12.2 billion New York City–based private equity firm Avenue Capi­tal Group, who had launched a new sports fund looking for opportunities in emerging sports leagues and teams. Strahan and Lasry met more than 15 years ago, bon­ding over their mutual love for watches.

In 2021, they participated in a $165 million fundraising round for the new and pre-owned luxury watch retailer The 1916 Company that also included Michael Jordan, Giannis Antetokoun­mpo, Bill Ackman and other famous faces. “We became friends, and then every time we’d see each other, I’d always notice he had a different watch, and vice-versa,” Lasry says.

Strahan is part of Avenue Capital’s team of fellow athlete investors—including Steph Curry, Lindsey Vonn and British soccer star Harry Kane. “Because of who Michael is, people show him a ton of deals and he will forward the ones he thinks are interesting to us,” Lasry says. “Ultimately, the real reason we’re able to get some of these deals is because the people on the other side want to partner up with Michael.”

Although he just ramped up his workload with Avenue Capital, Strahan, a father of four, says he has a retirement “window” now that he’s an empty-nester. “I have a soft landing in mind,” he says. “I won’t go cold turkey on everything, but I see myself slowly dropping different things until eventually you’ll just find me on the golf course.”

After all, the passionate watch collector learned a painful lesson about the value of time in the past year. In October 2023, his youngest daughter, Isabella, was diagnosed with a rare type of brain cancer at age 19. While she’s now in remission, the ordeal gave Strahan a new perspective that can’t be found on a Paul Newman dial.

“Time is the one thing that once it’s gone, you can never get it back,” he says. “I’m very conscious of that, being a dad. That’s what has led me to think more about the end of my career—I don’t want to be someone who’s on TV at 80 years old. It’s an absolute pleasure and privilege to be able to have that option. But I can get more of everything in life except for time.”