When the Duchess of Windsor, née Wallis Simpson, reportedly said “a woman can never be too rich or too thin,” she couldn’t possibly have imagined Lauren Jenai. The fitness entrepreneur is not only lithe as a cheetah, but she also pocketed $20 million from CrossFit, the gym-training empire she co-founded with her ex-husband, Greg Glassman.
Jenai lives in Portland, Ore., where she is preparing a new app-based diet and fitness concept, Manifest, to launch in December. And she’s planning a wedding to her new man, Franklin Tyrone Tucker, known as Ty, a childhood friend with whom she recently reconnected.
“I’m so in love, and I have never been happier,” she tells T&C.
But if there is a black fly in the Chardonnay, to paraphrase Alanis Morissette, it might be this: Tucker is currently in jail in Key West, Fla., awaiting trial on robbery and murder charges.
Tucker has been incarcerated since before the couple reconnected via a mutual friend on Facebook, and is not allowed visitors–meaning they haven’t spoken in person in over 30 years. On top of that, Jenai says she lost her video-call privileges for exposing her breasts during a chat, a violation of jailhouse rules. She also says she got busted trying to use her mother’s account to contact her fiancé—each infraction earning her a 100-year ban.
Nonetheless, wedding plans are going ahead, with a ceremony that could take place as soon as this month in the chapel of the Monroe County Detention Center on Stock Island.
The bride, 47, has sea-blue eyes, white-blonde hair and sleeve tattoos along the length of each arm. She is waiting to choose her dress so she can coordinate with the groom’s prison fatigues, which might be blue or black-and-white, depending on what permission he gets.
“Our first kiss will be our wedding kiss,” she says.
A $4 Billion Empire
Jenai’s first journey to the altar began in 1995. Then living in Santa Cruz, Calif., she fell in love with Glassman, a charismatic personal trainer at her gym. “He was kind of a big deal because he was up from L.A.,” she recalled. “There was a lot of buzz about him.”
Glassman was known for his intense, innovative workout regimes that produced remarkable results. “It changed my life,” Jenai says of his technique.
The couple married in 1998, and launched CrossFit together two years later. When they divorced in 2008, after having two boys and two girls together, they were living in Arizona, a community property state that splits marital assets down the middle.
Glassman was obliged to buy Jenai’s stake in the company for $20 million, and she says she’s worth “about that much” today. It wasn’t the ideal time to cash out: In 2015, one business writer estimated the CrossFit brand generated $4 billion in annual revenue. Today, it is available in 12,000 locations around the world.
Jenai also didn’t realize that while she was raising her children in the Grand Canyon state, the man she would eventually want to marry in 2019 was living only 20 miles away.
A Jailhouse Romance With Florida Man
Ty Tucker may have been nearby, but he was leading a very different kind of life. Working as a laborer, he drifted from Philadelphia, where he and Jenai met as teenagers, first to Arizona, and then, on foot, to south Florida.
A built man with a shaved head and greying beard, he survived by doing odd jobs, living for a time on a boat, and for a period in a homeless shelter, says Jenai.
On the night of November 17, 2017, according to prosecutors, he and two accomplices fatally stabbed a witness to a robbery they had just committed at a shanty dwelling on Stock Island, Fla. Local media dubbed it “the treehouse murder.”
Although he was named by the other two culprits, Tucker, 47, denies being involved, and his legal team says there is no physical evidence linking him to the crime. “The guy was down on his luck. He got involved with these transient people, and then this terrible thing happened,” Robert Hantman, a Manhattan-based attorney whom Jenai retained for Tucker’s defense, told T&C. “But his position is, he wasn’t there and he didn’t do it.”
Prosecutors from the office of Monroe County State Attorney Dennis W. Ward are relying on the testimony of Tucker’s alleged accomplices, as well as a jailhouse informant, who say he took part in the killing. He is charged with felony murder, as well as two counts each of armed robbery and wearing a mask while committing a felony, plus three counts of aggravated battery and tampering with a witness.
Larry Kahn, a spokesman for the State Attorney, said prosecutors are not seeking the death penalty. Nonetheless, Tucker faces life in prison if convicted.
Jenai is so convinced of her fiancé’s innocence that she offered to fund a $1 million bond, which could have allowed Tucker to travel to Oregon for the wedding. The court, however, denied that application. The next step for the couple is to take marriage counseling courses via telephone, which are required under Florida law.
$20 Million Rich, and No Pre-Nup
“Am I surprised about the relationship? I guess it’s unusual to have this kind of devotion between two people,” says Hantman. “Together, they hope that love and the law will bring lasting happiness.”
In the meantime, Jenai is standing by her man. “When I heard about what happened, my first instinct was this is nothing that Ty would do,” she says. “Since then, I have looked at all the evidence and there is absolutely nothing that suggests he was involved.”
“There are some people in my life, sure, who might think what I am doing is a little crazy,” she admits. “But my mom, who knows Ty, is supportive, and so are my kids.” The two boys and two girls are between the ages of 10 and 13.
In some ways, Jenai is repeating a pattern, mixing a new marriage with the start of a business. But this time, she is so confident about her relationship that she has declined to ask for a prenup.
Given the source of her own wealth, Jenai certainly understands how expensive a divorce can be. So, is either Florida or Oregon a community-property state?
“Good question, I don’t know,” she replies. “I should probably check on that.”
Contributing Editor Contributing Editor Ben Widdicombe reports for T&C on the nexus of privilege and power, and the bad—and occasionally good—behavior of the very rich.