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Booking agent Cara Lewis is once again representing Kanye West, working to revive his prosperous touring career that she architected in the 2000s and 2010s before he meticulously destroyed it after firing her in 2016.

Lewis has already had some early success, landing West and Ty Dolla $ign a headlining slot at Rolling Loud in Los Angeles March 14 to promote their new chart-topping album, Vultures 1. But in the long term, Lewis faces much more difficult odds undoing the damage West wrought on his own career, burning bridges with promoters, racking up multi-million-dollar lawsuits with vendors and production companies and making vitriolic and antisemitic statements that have gotten him banned by all the major talent agencies.

That leaves very little runaway for Lewis — “a self-described Jewish girl from the Bronx,” according to a 2023 profile in Pollstar — to relaunch West’s career. The saga is the talk of the town in both Los Angeles and New York, with more than six high-level booking agents telling Billboard that Lewis’ ability to produce business opportunities for West will be determined by West himself.

“He’s still on his bulls—, which means he is still in self-destruct mode and can’t work,” said one prominent booking agent who spoke on the condition of anonymity but said their agency was approached about representing West and passed. “I don’t take anything he says at face value. He needs to go away for at least a year and get sober.”

Lewis did not respond to a request for comment.

“There’s not really any upside for Cara,” says another booking agent who was also pitched on representing West. “She’s going to spend most of her time being told ‘no’ by promoters who have been burned by Kanye in the past. And any gigs she does land for him are going to be nightmares to get through.”

West has recently posted on social media about his booking challenges. On Feb 6, he took to Instagram to complain about the lack of interest from major arenas in hosting a listening party for his new album.

“We just sold out the United Center in seven minutes,” he shared in a video. “It’s the only arena that I had access to in the past year. And when I call, people say there’s no [availabilities] for me, and you know why that is.”

West made the video shortly after the O2 Arena in London rejected a similar request. He followed up that video by asking followers to contact Lewis for booking opportunities, showing a text message Lewis had sent to West expressing confidence about his future prospects. The post showing the text message was later deleted by West.

Kanye first began working with Lewis in 2006 when she was at the William Morris Agency, which became William Morris Endeavor (WME) in 2009. In 2012, Lewis quit WME to join CAA, bringing with her high-profile clients like Eminem, Ne-Yo, T.I. and West. Together, West and Lewis developed a touring strategy that generated $160 million in ticket sales, including his Watch the Throne Tour with Jay-Z, which generated $75 million in sales and was the highest-grossing tour ever when it wrapped, according to Billboard Boxscore.

Had West not stopped touring in 2016, he could have easily generated hundreds of millions of dollars in revenue from concerts and festivals in the years since. Even without any regular income from touring for the last seven years, West still ranks as the fifth highest-grossing hip-hop act in Billboard Boxscore history.

But instead of building upon their success, West fired Lewis and CAA and signed with UTA in March 2016. The Wrap reported at the time that West left CAA to expand his acting portfolio following the success of his cameo in Zoolander 2.

West returned to CAA a year later, but by then Lewis was already gone, working to launch her own boutique agency after she and CAA parted ways in November 2016.

While Lewis was setting up her new business, things really started going downhill for West. In October 2016, moments before taking the stage at the Meadows Music & Arts Festival in New York, West learned that his wife, Kim Kardashian, had been robbed at gunpoint in her Paris hotel room. He ended up canceling the set so that he could fly to France to be with her.

The Paris incident also led him to cancel two dates on his Saint Pablo Tour, ultimately returning to the road five days later on Oct. 7 to perform a show at the United Center. Fans noticed that West had seemed withdrawn and erratic on the tour, which eventually ended 20 dates early in Sacramento on Nov. 19, 2016, when West performed three songs before launching into a tirade about Facebook, Jay-Z, Hillary Clinton and Beyoncé before walking offstage. West was hospitalized two days later following a welfare check conducted by the LAPD.

An investigation by insurance company Lloyds of London, which West had hired to insure the tour, alleged that he was abusing alcohol and marijuana on the tour. The two parties eventually settled the dispute, court documents show.

In 2022, West was sued by Phantom Labs, a company he hired to help produce the Free Larry Hoover benefit concert with rapper Drake in December 2021. Six months after the concert, Phantom Labs sued West, saying it was owed “$7 million by Kanye in outstanding fees for work on various projects over the past year,” including the Free Larry Hoover concert and his 2022 appearance at Coachella, which Kanye canceled days before he was to take the stage.

“While West’s history is well known, I wouldn’t say the curtain has closed on his career quite yet,” said one promoter who has followed West’s career and didn’t want to be named in this article. “I’m going to reserve judgment until after his Rolling Loud appearance. If he pulls off a big show and people view it as successful, that will buy him a lot of goodwill and time. Perhaps some of [his] former partners can be persuaded to work out an agreement with him. Or maybe he will blow the whole thing up again. Either way it will be entertaining to watch, and we can all say we were there to see it happen.”