Britney Spears and Jason Trawick: He's Her Fiance, Manager & Conservator

After hitting rock bottom in 2008, Britney Spears’s X Factor debut is this week. Jason Trawick, her former agent, now manager/fiancé, is the man most responsible for Spears’s new career. But who is he? Ramin Setoodeh goes back to Trawick’s high-school days, interviewing close friends and colleagues.

Kevin Mazur, WireImage / Getty Images

It was supposed to be the wedding of the summer. Britney Spears’s third, actually, but momentous, nonetheless. The pop star, who just a few years ago had reached depths so low that she was seen shaving her head in public, had found love with her agent-turned-fiancé, Jason Trawick. The tabloids were speculating about a Hawaii wedding. But summer came and has nearly gone, and Britney hasn’t walked down the aisle.

Us Weekly landed a scoop that Britney was getting cold feet, that she no longer thought of Trawick as husband material. A source inside the Britney world talked to People and tried to swat away these rumors. Still, Spears—who once romanced a paparazzo and married a high-school friend for 55 hours—doesn’t have the best track record when it comes to men. And her fiancé is a complicated figure.

Trawick, 40, is often credited with performing a kind of Houdini act on Britney, 30. After her meltdown, which included losing custody of her kids, rehab, hitting paparazzi with her car, being institutionalized, and countless other crazy moments (like the disastrous performance of “Gimme More” at the 2007 MTV Video Music Awards), he—in tandem with her father, Jamie Spears—seemingly helped Britney reappear on planet Earth, at least looking normal. He accomplished this turnaround first as the agent who signed her to William Morris Endeavor Entertainment in 2008. In 2009, their relationship turned romantic. In 2011, Trawick quit his job to focus solely on Britney—and last December, they got engaged.

It’s hard to tell who benefits from this relationship more. Spears is one of the most successful acts in the history of pop music. She’s worth an estimated $200 million and her seven albums have sold more than 100 million copies. But in 2007, after the sad series of bizarre personal episodes, Britney’s career hit a wall. (Through her publicist, Spears declined to comment. Trawick offered to look at questions over email, but never responded.) She returned in her 2009 Circus comeback tour, during which Britney stood glassy-eyed in sold-out arenas, lip-syncing her old hits. Some people noticed the new Spears looked vacant, but it didn’t matter. The tour, an exercise in voyeurism, grossed more than $131 million.

Since 2008, Spears’s dad Jamie has been the sole conservator of her estate. In April a court appointed Trawick as the co-conservator, a situation that arises when a court decides a person “can’t adequately provide food, clothing, and shelter” for herself, says Meg Lodise, a partner at a Los Angeles law firm specializing in conservatorships. In other words, Britney has all the rights of a child.

Nevertheless, she’s poised to debut as a judge on The X Factor this week, and sources say that Trawick was key in convincing her to accept a $15 million, one-year contract to join the Simon Cowell singing Olympics. During audition rounds, gossip sites were salivating at reports that Spears frequently had to abandon her judge’s perch for a break—it became part of the hype of the show—and, according to one TV source, Trawick was always waiting in the wings. To prove that she’s normal, he’s booked her first magazine covers and talk-show appearances in a while.

The Britney press tour kicked off with a story in Elle magazine—Elle released images and interview snippets last week. Trawick appears in one of the photos; they cuddle as he holds a guitar. He also let it slip to the writer that Spears pursued him, not the other way around. “OK, that’s enough information, sweetie,” Spears said, interrupting the story. A few days later, a source told Radar Online that Trawick was lying and that he “had feelings for Britney for a very, very long time.”

According to those who know him, Trawick fell into Spears’s life during a rough time and stuck with her through her darkest days. (The court records on her health have remained sealed.) His former colleagues can’t recall exactly when or how Trawick’s working relationship with Spears turned into a romance, but once she became his girlfriend, she would occasionally visit the office.

“You see clients there all the time,” says a source that used to work at the agency. “But when she came in, it was like, ohmygod, Britney Spears is here! The whole office was whispering and the paparazzi would be outside.” Other than asking a receptionist for some water, she avoided any contact with the staff. “She didn’t say much. She’s like a cute, little shy girl.”

Shy or not, Spears gravitated to Trawick’s outgoing personality, and she started to rely on him more and more. He’s not the typical Ari Gold agent, with the greasy handshake and temper tantrums. According to one close former colleague, Trawick is so easy going, he never even raises his voice. Trawick grew up on Long Island, with dreams of becoming a professional hockey player. When those didn’t pan out, he moved to Hollywood and worked his way up from the agency mailroom. He had a reputation for inserting himself into meetings, but because of his nonthreatening demeanor, nobody objected. Once he became a full-fledged agent, he started handling crossover talent, such as singers who were big enough to big actors and vice versa. His roster included Taylor Swift, Hilary Duff, Paris Hilton, and country star Dwight Yoakam.

Beyond what his job required, Trawick lapped up the idea of being in the celebrity sphere and made pals out of the stars he represented. It’s not that he necessarily wanted to be famous; he simply likes the idea of being surrounded by fame. Despite being a Hollywood black sheep, Mel Gibson found a reliable confidant in Trawick and the two became very close. Trawick dated another client, the Australian actress and model Rachael Taylor. When Entourage star Kevin Connolly’s mother died in 2009, Trawick was the first to pack up and go to the funeral. He spent the weekend of the wake hanging out with Leonardo DiCaprio and Tobey Maguire. At the office, he had Ryan Seacrest on speed dial, whom he’d often nonchalantly call to shoot the breeze.

“Trust me, he has lots of friends in the industry,” says Darryl Cohen, head of product development at True 2 Beauty, a cosmetics website where Trawick works as a consultant. “Lots of people know him. It’s a known fact he represented Britney.”

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Unlike some of her previous relationships, Spears and Trawick share common ground. They both love Disneyland, and they both came from working-class families. Trawick grew up in Holbrook, N.Y. His dad was an executive at PC Richards. His mom was an art teacher at his junior high school. But Trawick was always driven to rise. When he was in high school, he negotiated a deal for himself that any agent would be proud of. He convinced his parents to let him move into the upstairs loft above the garage, with his own private entrance. He threw parties there—and his good looks made him a hit with girls. (I found his old yearbook on eBay. Back in high school, he looked kind of like a young Scott Baio.)

“Jason was very popular,” says a close pal since the first grade, Mike Simone. “We went to a huge school. His graduating class was 1,400. He was one of the most popular guys in his grade.” Simone chalks this up to his sense of humor—“probably one of the five funniest guys I’ve met.”

“I was very close with him, we played hockey together throughout high school,” says Bart Riccardi, another classmate. “He was a dependable friend.”

Trawick’s former work colleagues liked him, too. But looking back, they noticed a drastic physical transformation once he started dating Spears. The Daily Mail reported he lost 50 pounds by cutting carbs from his diet. He traded his bulky plaid shirts for fitted suits. He always brought a heavy-duty hockey duffel with him to work, but he hit the gym more often and toned down. “If he was working out, he wanted her to join him,” says a source. In an effort to be healthier, he and Spears both vowed to quit smoking together. (He failed.). And nearly everyone I interviewed stressed how good a parental figure he’s been to her sons—Sean Preston, who turns 7 this week, and Jayden James, whose sixth birthday is Wednesday. On Halloween, he’d order their costumes online and he was constantly buying them toys, like Spider-Man and GI Joe action figures.

Let’s remember that Trawick is romantically involved with a woman who has the same legal rights as a child. It sounds like a potentially difficult situation.

We fans and viewers won’t get a glimpse of the real Spears until October. That’s when The X Factor transitions from taped auditions to a live competition, and we see what Spears looks and acts like without the powers of editing. If she self-destructs in front of the world again, X Factor ratings will go through the roof, but at the cost of her own well-being.

“Britney always needs to be kept occupied,” says Steve Dennis, author of the unauthorized biography Britney: Inside the Dream. “She has rampant anxiety. Since a young age, she’s been told to run in a hamster wheel. If you get out of it, you still need to keep moving.”

In his book, Dennis argued that the turning point for Spears was when her father intervened and placed her in a conservatorship. “Where Britney stands now has to be viewed in the context of where she was in 2008,” Dennis says. “People are forgetting how remarkable her recovery has been. The conservatorship saved Britney’s life. It put stabilizers around Britney. Look at what surrounds Britney now—proper guidance.”

And Jason Trawick.