Before she was Sosay, she was Jennifer Elaine Kaiser, a Midwest farm girl raised with four brothers, a barn full of stubborn animals, and just enough rebellion to make her dangerous. Her early life reads like a Springsteen song—Southwest Michigan dirt roads, horses that bit, dogs that barked, and a young woman dreaming of something more than county fairs and Sunday sermons.
She was smart. Loyola University, Michigan State. Dual degrees in pre-law and studio art—one foot in the courtroom, the other smearing paint across canvas like she was wrestling her demons into submission. But law books weren’t enough. Gallery walls weren’t either. Somewhere between lectures and life-drawing classes, Kaiser got the itch for chaos—the kind of chaos only pro wrestling could offer. And like a good Bukowski anti-heroine, she didn’t walk in the front door. She kicked it open.
In April 2003, she stepped into the ring for Windy City Pro Wrestling under her real name. It was rough. Gritty. The kind of indie grind that separates the dreamers from the masochists. She didn’t just show up—she made noise. Beat Sandra D. Snatched the Ladies Championship. Then, just as quickly, she vacated it. Walked away to focus on art and personal training. That’s always been her move: leave just as they start paying attention.
But wrestling doesn’t let go easy.
By the end of 2003, she was in Louisville, Kentucky—ground zero for Ohio Valley Wrestling. This was developmental country. A proving ground. A meat grinder disguised as a wrestling school. It’s where you go to either make it to WWE or get eaten alive by someone who will. Jennifer Kaiser became Sosay—a sly, sultry heel with a secretary’s wardrobe and a con artist’s glint in her eye.
She didn’t throw punches. She threw shade. She didn’t need to wrestle. She could manipulate. The character—equal parts ruthless publicist and seductive schemer—was inspired by the likes of Stephanie McMahon but wore her ambition like a weapon. In Kenny Bolin’s Bolin Services stable, she played the “personal secretary” to Ken Doane, who would later become Kenny Dykstra in WWE. Onscreen, she was the power behind the throne—whispering, influencing, maneuvering.
Her first feud? Maria. They brawled in October 2003, their match ending in a no-contest, but the drama stuck. Sosay didn’t need clean finishes—she needed heat. She had brief feuds with Trinity and Shelly Martinez too, each one a study in mind games, not moonsaults.
Then came Jack Bull. A stuntman gimmick with a wild glint and a loose relationship with sobriety. Sosay became his publicist—a slick, manipulative power agent who looked like she belonged on the cover of Variety but moved like she was hiding brass knuckles under her clipboard. Together, they feuded with Joey Mercury. Chairs, chains, and a staged “drinking contest” that Bull won with the grace of a honky-tonk philosopher.
But Mercury wasn’t having it. On November 29, 2006, he smacked Bull with a chair, then hit Sosay with a double underhook DDT. It was a storyline injury, sure—but it was also a turning point. For once, Sosay wasn’t just whispering from the apron. She was taking bumps. That mattered.
She returned in January 2007, back in Bull’s corner as he challenged guys like Charles Evans and Justin LaRouche. But wrestling’s a cruel, unpredictable thing. Bull got cut from his developmental contract just two days after their angle climaxed. No warning. Just poof. Gone.
Sosay hung around, dabbling in Miss OVW contests and backstage segments. But the writing was on the wall.
Her final match came on April 25, 2007. A six-woman tag team dark match. She teamed with Beth Phoenix and Katie Lea—two future WWE stars—in a winning effort over Serena, Maryse, and Victoria Crawford. No cameras. No grand exit. Just the slow fade of a woman walking away while the rest of the world looked the other way.
She stayed gone for six years.
Then, out of nowhere, she showed up again. One night in April 2013, she returned to OVW and lost a dark match to Jessie Belle. A callback. A postscript. Two months later, she showed up in Chicago at 6 Corners BBQ Fest, teamed with Tony Atlas of all people, and beat Melanie Cruise and Robo De Luna in a mixed tag match. It was weird. It was glorious. It was vintage Sosay—come in, stir the pot, then vanish.
And just like that, she was gone. For good this time.
No Hall of Fame speech. No farewell tour. No sendoff hashtags. She walked away from wrestling the same way she entered it—quietly dangerous, with a crooked smile and something more interesting on her mind.
Since retirement, Kaiser’s been living her other life—the one she always kept simmering in the background. Artist. Trainer. Model. Creator. Her website is filled with fashion, color, and a sort of refined chaos that feels like a less bloody cousin to wrestling.
She didn’t leave because she was broken. She left because she had more to say than the ring could contain.
Jennifer Kaiser—Sosay—was never meant to be a wrestling lifer. She wasn’t chasing WrestleMania moments or diva photo shoots. She was chasing experience. Heat. A moment. And when she got it, she left with her boots still laced and her reputation intact.
You might’ve forgotten her.
But the smart ones? They remember.
They remember the woman in the pencil skirt with a devil’s grin and a head full of schemes.
They remember Sosay—the secretary of pain, the artist of the exit, the queen of the almost.