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Dead Man’s Float

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Seth and Phyllis Tobias's $5 million home, in Jupiter, Florida.  

In his early twenties, Tobias commuted from Philadelphia to New York on the 5:55 “Triple Nickel” train to a series of jobs on Wall Street. Some of the jobs worked out, some didn’t. At 24, he got his first break. That’s when Tobias began processing trades for a then-unknown portfolio manager named Jim Cramer. Tobias impressed Cramer, but the job didn’t last long. Tobias traded up to a position with the much larger JRO Associates hedge fund. Five years later, Tobias headed out on his own.

Tobias founded Circle T in 1996, at age 32. He named the company after the first letter of his last name, which he had tattooed on his left shoulder just after college. He started the firm with just one other employee, Steve Schwartz, a 25-year-old protégé of Tobias’s from JRO. He’d sit there in the middle of the room, taking in all the data and chatter, and then bark a buy or sell order. He seemed to have a gift for making the right call. “Seth could just tell when to get in and get out of a stock,” says Schwartz. “Seconds matter. He could see a movement in the cost of steel and figure out how that was going to impact companies that did business with GM and make a snap decision two, three moves ahead of other people.”

Tobias lived for what he called “the game,” and to him it was a game—who could analyze a company’s quarterly report or process a bit of information fastest and make the first move. He had a pet ritual after the market’s closing bell rang. He’d exhale, check his numbers, then call his friends at other hedge funds and ask them a simple question: “Are you up or are you down?” Simple.

In the early days of Circle T, Tobias was mostly up. By 2002, the firm was valued at almost $500 million, and Tobias was personally worth tens of millions of dollars. He bought homes—in suburban Philadelphia, on the Jersey shore, and in midtown Manhattan. He bought a luxury box at Veterans Stadium, where the Philadelphia Eagles played. A JRO colleague introduced Tobias to some pals at CNBC, and Tobias became a regular on the network’s Squawk Box program.

Tobias also liked to party. His longtime friend Patrick Bransome said in a recent deposition that there were many nights when Tobias would get so loaded he had to drive him home. Bransome would drop his friend on his couch and leave once Tobias passed out.

“Look, Seth was a little crazy,” a former colleague told me. “But we all are. You have to have a screw loose to be in this business and take the risks. You have to blow off steam, or you’ll combust. He liked to blow off steam, too; we’d go to strip clubs and go out drinking. He just blew off steam a little harder than most.”

It’s shortly after New Year’s, and I’m in the West Palm Beach office of Jay Jacknin. Jacknin, Phyllis Tobias’s third husband, is serving as counsel to his ex-wife in the death of Seth Tobias. He’s a short, jolly man with hearing aids in both ears. At one point, he reaches into a file and brings out a picture of Seth and Phyllis on a beach. He starts to make a point about the case but then offers an aside. “She had a great body,” he says. “Women love her. Men find her fascinating. I just couldn’t afford her.”

Phyllis Tobias was born Filomena Manente in 1966 and was raised in Union City, New Jersey. She was brought up by a strict Italian family, and went to Catholic schools. Now and then, she worked as a waitress. Her nickname, a nod to her personality, was Sunny. Just after she graduated from high school, in 1984, she married Vince Racanati. She was 18, he was 24. They had a daughter but got divorced after a year. Phyllis took a job as a secretary on Wall Street, where she met and married a twice-divorced stockbroker named Arthur Tolendini. That was 1987. They lasted just three years.

Phyllis moved to Palm Beach and was selling insurance when she met Jacknin, a divorce attorney. They got married in 1993 and had two children. But in October 2002 Jacknin filed for divorce, claiming Phyllis had gotten numerous credit cards without his consent and run the balance to the maximum. Jacknin didn’t move out of the couple’s home after they separated. He was worried about his two children. Phyllis was furious about that. The police were summoned three times in 2003, and each time, Jay Jacknin said his wife was the aggressor. He said she struck him, threw a phone, and pulled his hair.


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