By Scott Jacobs

So, first impressions of Si . . . he walks around his club (“Teasers”) with a big grin on his face, his eyes peeking out from under a baseball cap that says “Boxing’s Most Feared Manager.” My guess is he must be 70 or so and it looks like the last time his body saw a coat-and-tie Reagan was president.

One of his girls – there are 118 in all, a dozen or so always on call to dance – comes up and gives him a big kiss. “This is the most beautiful girl in the world,” he says. There are some who think Si is a bit daft. If he is, there is method in his madness, because his method tonight is to hug her back.

Over the din of the music, Si launches in on his favorite topic, which is not girls, Key West, or the college students on Spring break that now fill his club, but boxing. He is just back from the Pacquaio – Clottey fight in Houston. (“A total waste of time. Clottey lost every round. He never even fought.”) But he can hardly wait until Saturday when Top Rank Boxing brings the whole show to town for “Fight Night in The Keys.”

In the great tradition of Ernest Hemingway––a tradition, by the way, that is not as great as you might imagine––Key West will take its place in boxing’s center ring. Top Rank will stage a heavyweight title match between Cuba’s Olympic gold medalist Odlanier Solis and Costa Rican champion Carl Davis Drumond outdoors before 5,000 fans in Key West’s famous Mallory Square. The Fox Sports Network will broadcast it to 93 million homes, and ground zero for all the action will be Teasers, Si’s strip club on Duval Street and Big Uns, the sports bar he owns below it.

For the last five years, Si Stern and his partner Dave Johnson have been building “Fight Night in the Keys” into a Key West institution. The literary crowd has its “Hemingway Days.” The gay community celebrates “Fantasy Fest.” Now fight fans will have their day as well and, although Johnson is the promoter of record, everyone knows this is Si’s baby.

In the weeks leading up to the event, Si lives and breathes boxing. He pumps it on the radio, promotes it at the club, sells the tickets (or gives them away to car valets), picks the ring girls, even manages some of the fighters. For some reason this year, Si has decided that is not enough. This year, Si wants something special at Fight Night in the Keys. This year, Si has decided he needs a writer.

Flying In

The American Eagle turbo-prop lifts off from Miami International Airport and banks sharply south over suburbs, then farmlands, then a murky kind of greenish-brown swamp called The Everglades. Only from the air do you fully realize that southern Florida has no border just this soft green goo that oozes like lava into the sea. Slippery fingers of swampland break into small isles and islets, hundreds of them (800), mostly uninhabited, some little more than reefs with water skimming over the top, and pretty soon there is more water than land, and no more Florida.

I’m headed to Key West, one of only 30 of these islands large enough to sustain any kind of human community. Only 90 miles from Havana (and 168 from Miami Beach), it is the southernmost point in the United States. From the time Ponce de Leon first charted its existence in 1513, Key West has been a haven for characters who didn’t quite fit in anywhere else. The Spaniards called it Cayo Hueso, or bone key after finding the bones of massacred Indians scattered on its beaches, and for the next 300 years that’s about all you could find there.

Once control transferred to the United States in 1822, however, the scoundrels started moving in. Key West’s history thereafter can be divided into four eras: The Shipwreck Years (1830 – 1890) when small fortunes were made salvaging cargo from sunken schooners in the Florida Straits; The Heyday (1890 – 1930) when Key West flourished as Florida’s largest city (pop. 18,800) and Henry Flagler built his railroad through Florida in a vain attempt to make it a vacation destination; The Romantic Years (1930 – 1960) when Ernest Hemingway, Tennessee Williams and Robert Frost were frequent guests there; and The Margaritaville Years (1977 – present), when Jimmy Buffett’s song “Wasting Away in Margaritaville” turned Key West into a refuge for anyone wishing to partake of the drugs, sex, liquor and lifestyle it celebrates.

When Si called to ask if I would come down for Fight Night, it took me all of a New York second to say yes. He knew all the words that inspire a Chicago boy ­–– seventy degrees, all expenses paid, front row seats, “and did I mention, I run the largest strip club in the Florida Keys”–– because Si once was a Chicago boy himself, if you can call a 73-year-old a boy.

The Sweet Life of Si Stern

Si was born Silas Stern in 1937 in Garfield Park Hospital to a family of strictly observing Hassidic Jews from Humboldt Park. His family moved to Albany Park where he attended Roosevelt High School, then on to Los Angeles, where he followed in the footsteps of Sandy Koufax at Fairfax High School. (“I never attended a school more than two blocks from a deli,” he jokes.)  He tried his hand at a variety of sports, but excelled at tennis. “He plays a lot like Bobby Riggs,” his son Gary, 49, says. “He lures you in by claiming he’s not very good, then drives you crazy with lobs to the corner.”

When he was 19, Si found himself in the finals of a tennis tournament that took place on a Friday night. If he played, it would mean breaking the Sabbath. His father warned him never to return home if he did. Si went to the match, and kept going, eventually landing in Miami Beach where he got a job working as a bellman at the Fontainebleau Hotel.

This was in the 1950’s when Cuba was still considered a Florida colony. Fidel Castro had yet to come to power and Havana’s Riviera was a wild strip of beaches, casinos, nightclubs and showgirls. Si would go frequently on weekends to sample the nightlife and carouse with his buddies. One of them sold television sets for Admiral. Another, a Memphis businessman named Kemmons Wilson, was about to start a chain of motels called Holiday Inns.

In his first job in the television business, Si put the two of them together in a deal to furnish Admiral TV’s to all the Holiday Inn rooms in America.  The deal was so lucrative that when Motorola acquired the Admiral brand, the company made Si vice president of its television division. He rose in the ranks to become president of Quasar and GTE, ran a cable company in Ohio for a few years, and was living on Astor Street in Chicago, developing a hotel venture in Hoffman Estates, when a huge blizzard struck Chicago in 1988. The wind chill was below zero. Traffic on the Kennedy was at a standstill, and his car was dead. “If I get out of this car, I’m never coming back,” he told himself. Then he climbed out.

It took three years, but Si moved to Key West in 1991. He was 54 and single. He’d accumulated enough pension rights to retire three times over. His two children were grown. He had every intention of never working again — until another “opportunity” presented itself.

Never Miss an Opportunity

Opportunity has been the watchword of Si’s life. In Key West, it was an opportunity to buy a small bed and breakfast, and double its size; then an opportunity to buy a little strip club called Teasers, and move it downtown onto Duval Street. Enough other opportunities have arisen that Si has a dozen business interests on the island. Key West natives tend to be naturally suspicious of anyone not born and bred on the island, but Si has a foot in the door of every civic endeavor. He’s contributed money to help furnish the police department gym, construct the high school scoreboard, support local tourism and dabble in politics. But what Si contributes most is his enthusiasm.

“It’s fun watching Si work. He’s like a 5-year-old,” says his friend Reggie Long, a trainer in Chicago. “He gets so excited. You don’t always know where he’s going with an idea. The only thing you know for sure is that anything he touches turns to gold.”

Still Promoting

It’s going on midnight and Si is still pumping Fight Night in The Keys, although he has moved on to plug the individual boxers he will have fighting that night. There’s Marcus Upshaw, the nephew of NFL players union head Gene Upshaw, fighting for the Florida state middleweight belt; and Damian Frias, a Cuban out of Miami’s ghetto, “who is a great story”; and Danny “The White Lion” Van Staden, who also happens to manage the girls at Teasers.

Si rattles off the names of other VIP guests he wants me to interview. We make arrangements to meet tomorrow because suddenly his eye catches something amiss at the other end of the bar. “Have a drink. Enjoy the show,” he says, “We’ll talk more in the morning.”


As soon as Si steps away, a dancer by the name of Mary Jane takes a seat beside me. In the ten minutes before she goes up on stage, she coaxes a cream soda and Tequila shot out of me for ten bucks. (I, in turn, coax from her the fact she pays $40 a night to dance, keeps what she earns from lap dances, less tips for the bouncers and DJ, and makes $20 to $2,000 a night, depending on the clientele.)

The nice thing about working for Si, she says, is she can do what she wants as long as she stays clear of anything that might be construed as prostitution. There’s nothing sleazy about Teasers. It’s a job, and a legal one in Key West, not worth jeopardizing for a few extra bucks. What she offers customers is the illusion of sex. Most of the dance takes place in her customers’ heads. Her body is just the canvas on which they paint their dreams. To get those dreams going, she dresses like a schoolteacher with flowing black hair and heavy-rimmed black glasses – in a neon green latex mini-skirt.

When her turn comes to dance, Mary Jane slips off her stool. (“Watch this. I’m going gansta!” she says.) She mounts a stage with two poles in the middle of the room, starting at the back pole half-clothed and ending ten minutes later totally naked at the front one. Other girls are more athletic, shimmying up the pole and doing various acrobatic tricks as they undress on the way down, but Mary Jane has mastered the art of watching the boys watch her in the mirrors on the wall.

She catches the eye of a guy who is pretending to watch TV and comes over to engulf his head in her breasts. He slips a dollar in her garter for the favor. Another boy grins ear to ear and leans forward on both elbows with a twenty dangling from his teeth. She snatches it from him with her tits. He pulls out another. She does it again. He looks like he died and went to heaven.

Midnight on Duval Street

Outside on the sidewalk, a street hawker sounds the clarion call for Teasers – “Hot naked ladies and alcohol.” At Hemingway’s favorite bar Smokey Joe’s down the street, a half dozen college girls take the stage to sing “My Sharona” with the band. A fat man in a bra dances in the window of the Bull & Whiskey. A man with “$2 a beer” painted on his belly sells liquor from a T-shirt shop.

In the cab back to the hotel, the driver says this is all par for the course during spring break in Key West. During spring break, he can make $600 a night driving students around. The rest of the year he stays closer to his charter fishing boat. I ask him if he happens to know Si Stern. He smiles.

“Everybody knows Si,” he says. “He’s a great guy. He does things the Key West way. He does good by people, and people do good by him.”

Coming Next Week: FIGHT NIGHT IN THE KEYS Part II: The Pound for Pound Boys.

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