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He’s been kicked out of a company. He’s been through a $750 million divorce. He argued down the ransom demands of men who kidnapped his daughter. He even put his elbow through a Picasso. But Steve Wynn has never been in a pickle quite like this.

Elaine Wynn has asked a federal court for permission to sell the Wynn Resorts (WYNN) shares she was awarded in the couple’s 2009 divorce. A sale of even half of her 9.6 percent stake could trigger a series of events that would threaten her ex-husband’s sway over the $13 billion gaming company, his lavish, company-financed lifestyle—and possibly his personal fortune. “She’s the swing shareholder,” says William Thompson, a professor emeritus at the University of Nevada, who studies the gambling industry. “This could be the final damper on the guy.”

Shareholders have a lot riding on the suit: They’ve enjoyed an eightfold gain since 2009 under Wynn’s leadership. The company, whose flagship casino is the most profitable on the Las Vegas Strip, has said it would face a serious business risk if Wynn, 71, left or even got distracted. “If we lose the services of Mr. Wynn, or if he is unable to devote sufficient attention to our operations for any other reason, our business may be significantly impaired,” the latest annual report said. “Our ability to maintain our competitive position is dependent to a large degree on the efforts, skills, and reputation of Stephen A. Wynn.” Wynn did not respond to e-mailed questions. A company lawyer, Kim Sinatra, declined to comment.

Elaine filed a claim in federal court in Las Vegas last June seeking to void an agreement that restricts sales of her shares and forces her to vote them at her ex-husband’s direction. She acted in the wake of Wynn’s ouster of Kazuo Okada, his former partner and co-founder of Wynn Resorts’ predecessor company. In 2012, Wynn Resorts stripped Okada of his shares after accusing him of bribing Asian casino regulators, which Okada has denied. The company issued a $1.9 billion note to buy the stake. Elaine, who declined to comment for this story, argues in court papers that she only agreed to the lockup because Wynn insisted that if she sold shares, so might Okada, the top holder at the time, and that would undermine the chief executive officer’s influence on the company. Wynn called her demand “legally baseless.”

Wynn is effectively the company’s largest shareholder because he owns 9.9 percent of the stock and controls his ex-wife’s shares. If Elaine prevails in court, “Steve Wynn would not beneficially own or control Elaine Wynn’s shares and a change in control may result” under the terms of the company’s debt agreements, according to company filings. Once that happens, the company says it must offer to buy back $3 billion in bonds. The company, which has said it’s heavily indebted, might have to borrow more money to finance such a buyback. That could lead to a lowered credit rating and complicate the completion of a $4 billion casino project in Macau with 1,000 guest rooms, Hermès (RMS) and Prada (1913) boutiques, and antique Chinese porcelain decorations that Wynn bought at auction. The judge in charge of the case hasn’t set a date to hear Elaine’s claim.

Introduced by their fathers, Elaine and Steve became college sweethearts at the University of Pennsylvania, Elaine said in a 2005 television interview with Charlie Rose. They married in 1963, divorced in 1986, remarried in 1991. Their second divorce was finalized in 2010. “I am Steve’s confidant,” she told Rose. “I think I’m the person he trusts the most.” Wynn met his current wife, Andrea Hissom, on a yacht in the French Riviera in 2008, according to the Las Vegas Weekly. He married her in April 2011. Elaine sits on the company’s board of directors, participating in shareholder meetings that Wynn’s new wife also attends.

Okada, chairman of Universal Entertainment (6425), which makes Japanese pachinko gaming machines, has sued Wynn Resorts to get his shares back. In the suit, he alleges the company donated $135 million to a fund that supports the University of Macau in hopes of getting a casino license there. Wynn Resorts termed it a “spurious” theory. The U.S. said in a court filing it has launched a criminal probe of Wynn Resorts’ Macau donation, as well as of Okada’s alleged payments to regulators elsewhere. Okada would not comment for this article except to say he’s cooperating with investigators. Wynn Resorts has said it will cooperate in any investigation.

As CEO, Wynn took $17.7 million in compensation and $92 million in dividends last year, filings show. His perks included corporate aircraft use valued at $1.2 million, as well as a 6,522-square-foot home at the Wynn Las Vegas Fairway Villa resort. If Wynn were to lose control of his casino empire, it wouldn’t be the first time. He was ousted from Mirage Resorts in 2000 by Kirk Kerkorian, MGM Grand’s majority owner, getting $11 million in severance. Investors were unhappy then with Wynn’s spending on new projects and a company art collection. His severance deal with Wynn Resorts calls for him to be paid as much as $239 million if he’s demoted or forced out by a majority owner, according to company filings.

Wynn could maintain his grip on the company by acquiring Elaine’s shares, which were valued at $1.27 billion as of April 24. His net worth is $2.3 billion, according to the Bloomberg Billionaire’s Index. In November, Wynn sold the crown jewel of his private art collection, Picasso’s Le Rêve, to hedge fund billionaire Steve Cohen for $150 million. (He had agreed to sell the painting to Cohen in 2006, but the transaction was canceled after Wynn, who’s legally blind, accidentally damaged the canvas. It’s been repaired.)

Wynn Resorts without Steve Wynn would be a very different company. He “has a magic touch,” says the University of Nevada’s Thompson. “He’s the best developer we’ve had, and he’s the force that revived Las Vegas.” Still, Elaine may be one challenge he can’t overcome. “He’s Mr. Charisma in gaming,” says Thompson. “Part of having charisma is you fall down but you always get up. Maybe this time he doesn’t jump back.”

The bottom line: If Elaine Wynn wins the right to sell her shares, valued at $1.27 billion, Steve could find himself struggling to hang on to his company.