As chairman of Loews Hotels & Resorts, Jonathan M. Tisch oversees 18 four- and five-star hotels in the US and Canada. But there’s only one of them that he regards as a personal rite of passage: the Loews Miami Beach Hotel. H e says, “Loews Miami Beach was my bar mitzvah.”

It wasn’t just that Tisch quarterbacked the effort to win the right to develop the hotel—or that Loews triumphed over a gaggle of hotel Goliaths, or even that he pulled rank on his father, Preston Robert Tisch, who ran the Loews empire at the time, over the final presentation. It’s that the ultimate pitch included a video of Tisch, dressed in drag—“high heels, lipstick, rouge, a curly wig, and even a set of Lee Press-on Nails,” he recounts in his book The Power of We—pretending to be a reporter, and doing man-on-the-street interviews about the prospect of South Beach’s first new hotel in decades. (In fact, the Loews Miami Beach, which opened in 1998, was the first major hotel to open in South Beach since 1967, and with 842 rooms, it is still the city’s second-largest after the Fontainebleau Miami Beach.)

The video was Tisch’s idea—Loews had to do something out-of-the-box to win the competition, he felt. It was inspired by David Letterman’s sending his mother to report on the 1994 winter Olympics in Lillehammer, Norway, and it concluded the Loews presentation. A claustrophobic silence ensued. And then, just like a Hollywood ending, someone laughed, which led to a prairie fire of hysteria. It is still the longest Hail Mary touchdown pass in the city’s history.

Jonathan Tisch seems the least l ikely CEO in America to do something so crazy that it just might work. He’s the CEO as statesman, the travel industry’s chief ambassador in his role as chairman emeritus of the US Travel Association. He also has a string of blue-chip accomplishments: He’s written three books; hosts an Emmy-nominated TV show about business; for six years headed NYC & Company, New York’s tourism marketing agency; sits on the board of the Tribeca Film Institute; helped bring Super Bowl XLVIII to New York (as a co-owner of the Giants); and has a College of Citizenship and Public Service at Tufts University, his alma mater, named after him.

In person, Tisch is deliberate, articulate, soft-spoken, but with sudden bursts of feeling (which he lassos back quickly). He’s candid, asserting that he was not optimistic about the summer weekend business in South Beach, but that the destination excited him. “It was a community that had soul, vibrancy, excitement,” he says. He’s modest, crediting Tony Goldman, Craig Robins, and Ian Schrager for creating South Beach. “It has grown even beyond my expectation,” he says.

Tisch has repeatedly shown that he’s not afraid to step out of character. In March 2004, he appeared in a reality-TV program on The Learning Channel called Now Who’s Boss? The idea was to have top executives experience life at the bottom rung of their company ladder. Tisch worked as a room-service waiter, bellman, front desk assistant, and even cleaned bathrooms, under the eyes of a supervisor, no less. On the show, Tisch is the new hire looking to win employee of the month, but then, he also takes a small walk on the wild side, asking a guest at check-in if he was a Dolphins fan (yes) and then kidding him about not being a Giants fan.

The act wasn’t just an act. Based on his experience, Tisch changed the fabric of staff uniforms (they were too hot) and cut to make employees look hipper, he says; tweaked the technology to speed up the check-in process; and got a lesson in humility as a room-service waiter, noting that a guest made eye contact with everyone in the elevator except him.

Tisch goes back a long way with Miami. In 1957, the Tisch family commissioned Morris Lapidus to build the Americana Hotel here. The Bal Harbour Shops now sit on the space that was the Americana tennis courts. And he’s in on the future of Miami. He knows that it’s America’s portal from Latin and South America, and to that end Loews Hotels & Resorts worked with the US Secretary of Homeland Security to promote the Global Entry and TSA Pre programs, in which Loews paid the $100 fee for its top-tier guests to enroll online to be eligible for US Customs and Border Protection expedited screening—at immigration, members could skip the lines and use an automated kiosk. (The one-time program ended last November.)

Tisch is in Miami six times a year to “work on the vision, design, and feel of the hotel” and—in classic Jonathan Tisch form—“do a walk-through and say hello.” He says that Miami has “a feel to it that’s just electric.” He’s an early riser, and the thing he loves about South Beach is “walking in the morning and being able to see what’s happened the night before.” He frequents the News Cafe and Van Dyke Café. His favorite restaurants express Tisch’s buttoned-up side: Joe’s Stone Crab, Prime One Twelve, Estiatorio Milos, The Dutch, and Zuma (which he hopes “comes to New York one of these days”). He canvasses the competition but not undercover—“It’s a bit hard for me to be anonymous”—and for the record, he thinks that the rooms at the W South Beach are “outstanding.”

Back in 2004, Tisch wrote these words in the opening chapter of The Power of We: “The reality is that virtually every business relies on social and governmental resources for part of its success. The myth of the go-it-alone business hero is just that—a myth.” It’s an iconoclastic position, but it didn’t garner a whirlwind of criticism.

Fast-forward to 2012, when a sitting president said the same thing, but in a pithier, more populist way: “If you were successful, somebody along the line gave you some help.” Result: Category 1 storm with sustained winds of about three months.

The political climate has grown a lot more acidic since 2004, but Tisch is still offering above-the-fray wisdom. He advocates intelligent business-government partnerships, like the one that brought Loews to Miami in 1998. He thinks America should work harder to put out the welcome mat to international visitors—“open doors but secure borders,” as he phrases it—as a way of creating jobs. He also applauds the surge in wealthy Latin and South American visitors to Miami. And when it comes to travel, he’s still a romantic. “Our industry is the American dream,” he says.

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