A sit-down with the billionaire in the Big (Red) Apple behind St. Pete's next great skyscraper

NEW YORK CITY — Billionaire John Catsimatidis has a favorite word: opportunity.

It was opportunity that led him as a college kid to buy the small grocery store where he worked, eventually parlaying it into Manhattan's biggest supermarket chain. It was opportunity that launched his Red Apple Group from soap and cereal into aviation, heating oil, insurance, finance, real estate and gas and convenience stores.

And it was opportunity that prompted Catsimatidis to pay $16.5 million cash in April for an entire block in downtown St. Petersburg, a city that he has visited for years — his wife's 98-year-old father still lives there — but that he never thought was exactly flush with possibilities.

Then, "all of a sudden, the city government seemed like it was a little more progressive in encouraging investment," says Catsimatidis, who is keeping a close eye on St. Petersburg's mayor race. "It's not as if we were looking for any investment but if somebody shows it to me and it's a good deal, I'll look into it. When the offer was made for the land in St. Pete, we wrote a check."

PREVIOUS COVERAGE: Red Apple Group buys coveted St. Petersburg parcel for $16.5 million

It is a Friday morning in Red Apple's headquarters, which cover the entire fifth floor of a high-rise office building in midtown Manhattan. Catsimatidis — whose hobbies include hosting a Sunday morning radio talk show — has just finished taping an interview in a room dominated by a big red glass apple. From there, he moves across the hall into a cluttered conference room. On one wall: An artist's conception of a soaring tower in St. Petersburg.

Despite the rendering, Catsimatidis acknowledges that plans for the 400 block of Central Avenue are still in the preliminary stage as discussion continues over the best use of two vacant acres in the heart of a dramatically reenergized downtown.

"I understand the city would like 200,000 (square feet) of office, 200,000 of hotels, lots of parking," he says. "It's a lot of land. We could have a separate hotel, a separate office building."

But the 68-year-old Catsimatidis appears to have made up his mind in one regard: "We want to build a nice condo tower with great views. It will have balconies. I love balconies. You've got to be able to breathe fresh air."

Cleared of all structures and attractively landscaped, the Central Avenue block probably will remain a fenced private park for at least a year. But Catsimatidis — who also bought a small building across the street for Red Apple's Florida headquarters — is poised to become a major player in downtown St. Petersburg's redevelopment just as he has become a well-known if sometimes eyebrow-raising figure in the city where he grew up.

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'Common billionaire' politician

Born in Greece, Catsimatidis was just six months sold when his parents moved to New York. He dropped out of college a few credits shy of graduation as he began building his grocery empire -- offering such innovations as check cashing and free delivery -- with stores under the names Red Apple, Gristedes and Sloan's.

By age 24, Catsimatidis was making $1 million a year. Now, he ranks No. 581 on Forbes' list of the world's billionaires with a net worth of $3.3 billion, millions of which go to philanthropic causes.

As Catsimatidis' businesses grew, so did his time in the public eye. Lining Red Apple's walls are dozens of photos of him with the famous, ranging from Fidel Castro and Cesar Chavez ("The poison on the grapes killing his workers also hurt my customers") to Ronald Reagan, Barack Obama and Bill Clinton. He has been especially close to Clinton, hosting fundraisers and letting the former president use his private jet.

Catsimatidis, who sports an American flag pin and a tie covered with little eagle heads, said he pays no attention to political labels when contributing.

"I look at people I consider good people who want to do the right thing," he says.

It was as a Republican, though, that Catsimatidis broke into politics himself, running for mayor of New York City in 2013 as a "common billionaire" who would create jobs and improve public safety. He faced an uphill fight, partly because some voters considered his Gristedes stores dingy and overpriced, partly because of his unorthodox campaigning style.

"Mr. Catsimatidis — whose smiling photo still appears at the top of Gristedes coupon fliers — has proved an exuberant and disruptive presence," the New York Times said at the time. "He swore at an audience member who questioned him at a Young Republicans' meeting, expressed skepticism about global warming at a sustainability event (he was booed), and once trailed off midsentence at a candidate forum, telling the puzzled audience, "Sorry, lost my train of thought."

Catsimatidis was defeated in the Republican primary and recently abandoned thoughts of another try at the mayor's office, deeming the chances of anyone beating incumbent Bill de Blasio as "slim to none."

As his New York grocery stores dwindled in number, victims of soaring rents and increased competition, Catsimatidis moved into other ventures including real estate. He owns "three or four blocks" on Coney Island where he plans to build residential towers. As a result of buying dozens of Pantry Pride supermarkets in Florida in the 1980s, "I owned 40 shopping centers from Key West to Riviera Beach," he says.

Those have since been sold, and Catsimatidis is now focused on the Tampa Bay area, calling himself "almost a native of St. Pete."

Deep St. Pete connections

His initial ties to the city were through his wife, Margo. An Indiana native, she had moved to New York to purse a career as a ballerina but went to work as a temp for Red Apple after breaking an ankle. She and Catsimatidis married and had two children, John Jr. and Andrea, both executives with the company.

Decades ago, the Catsimatidises began going to St. Petersburg to visit Margo's retired parents. The gregarious Catsimatidis got to know many prominent locals including then-Mayor Rick Baker, who "attended all of my wife's New Year's parties," he says.

Catsimatidis clearly keeps up with local happenings that could affect his investments. He comments that "a lot of people have gotten behind" Baker in his current race for mayor against incumbent Rick Kriseman. But asked if plans to contribute to Baker, he quickly adds: "The other fellow seems like a decent guy, too."

Among those in the bay area especially close to Catsimatidis is U.S. Rep. Gus Bilirakis of Tarpon Springs, who was best man at Andrea Catsimatidis' wedding to one of Richard Nixon's grandsons. (They have since divorced).

Another Greek-American House member seems less in favor.

"Charlie Crist was sitting in that chair where you are two days ago," Catsimatidis tells a reporter. "He was trying to raise money. I've known Charlie since he was governor and he p---- me off. He didn't show up to my wife's party."

Catsimatidis doesn't remember which of his local contacts steered him toward the downtown St. Petersburg block, which he acquired after feuding owners resolved a long-running dispute. But he saw opportunity, even if it's not clear exactly what form it will take.

"We didn't come here with a preliminary agenda other than to do a beautiful building," he says. "I don't mind spending money, I want to be proud of what we're doing."

Even as Red Apple executives meet with architects and hotel companies about plans for the St. Petersburg property, the company remains on the look-out for other opportunities.

One hint: "I love the beach," says Catsimatidis, who likes to stay at the TradeWinds Island Grand Resort on St. Pete Beach.

Another hint: On a recent trip to Florida, he had breakfast with Tampa Bay Lighting owner Jeff Vinik, who is involved in a $2 billion makeover of Tampa's Channelside area.

"He wanted to meet us and tell us what he's doing in Tampa and the opportunities," Catsimatidis says.

In addition to real estate, he considers the bio-medical field ripe for investment "because people want to live longer." He and some family members have diabetes, so he is especially intrigued by talk that Apple is developing a device that continuously and non-invasively monitors blood sugar levels.

One business where Catsimatidis sees less opportunity is the one where he got his start almost 50 years ago.

Grocery stores are "going to have to change more or die," he says. "Every drug store now is a food store."

Contact Susan Taylor Martin at smartin@tampabay.com or (727) 893-8642. Follow @susanskate