The first time Antoinette Vigilante asked her wealthy husband Patrick Arbor for a divorce was around 2003, citing serial adultery on his part over their 10 years together.

Arbor, the former head of Chicago's Board of Trade, had other ideas. He bought her expensive jewelry, including a $17,000 necklace from the Italian island of Capri, and convinced her to stay married. She agreed—on the condition he stop sleeping around and give her his email passwords and a complete list of his bank accounts. She was 56 and he was 71 at the time.

“He was very charming, persuasive and cunning,” Vigilante told The Daily Beast in a telephone interview. “He's a politician—one of the best Chicago has ever seen.”

Nine years—and what Vigilante contends were countless extramarital affairs—later, she asked for a divorce again. That's when he started emptying the bank accounts and selling off his investments, she says. He did agree to the divorce, apparently having an exit plan underway that would cut his soon-to-be ex-wife out of a fortune she says they built together.

But the plan, it turned out, was not foolproof.

As a result, Arbor, now 82, is spending the holidays in a Chicago jail, where he has been locked up for the last seven months on contempt of court charges. The courts have ordered him to turn over $18 million to Vigilante. But depending on who you believe, he either can’t or won’t.

“I’m sure he says I‘m a gold digger, that I’m just after his money,” Vigilante says. “But the fact is that we were together over 20 years. He had a plan—it was to flee. He took all his money. He annihilated me financially and left me high and dry.”

During the interim between the first time Vigilante asked for a divorce and when he finally granted it, Arbor pushed to get his Italian passport based on his ancestry in Italy, which allowed him to easily travel to Europe.

“Behind my back I found emails that he was searching for apartments in Lugano,” she said, referring to the resort town on the Italian-Swiss border. “He was stashing money and counting the money he already had stashed.”

In late 2012, just as their nasty divorce proceedings got underway, Vigilante warned the court that, as an Italian passport holder, her husband could easily flee. She insisted that his U.S.-based accounts be frozen. The court initially did freeze all the accounts they knew about, but then his lawyers were able to get them unblocked, convincing the judge that because Arbor was elderly and battling cancer, he was not a flight risk.

But Vigilante was right. Days before a Cook County divorce court awarded Vigilante an $18 million payout, Arbor skipped the country. It soon became clear that he had long before transferred vast sums of money abroad.

According to the Chicago Sun-Times, which has reported the twists and turns of this saga in detail, the financier divided his money between banks in Panama, Zurich, Portugal, Dubai, the Channel Islands and Liechtenstein.

Howard Rosenfeld, Arbor's lawyer, was out of the country and unavailable to comment about the case. But in a jailhouse interview with the Sun-Times earlier this month, Arbor said was the victim of “persecution.” He claimed he lost nearly all of his money and cannot access a few million in an “asset-protection trust” in Lichtenstein.

“I’ve complied with every one of their demands, orders and wishes… The judge and the malfatorre want to keep me here,” he said, using his nickname for Vigilante, which is the Italian word for “evil one.”

Arbor, who was until recently listed as a principal at the Shatkin Arbor trading firm and as a trustee at Loyola University of Chicago, once ran as a Democratic candidate for lieutenant governor of Illinois. “Of course, my record is impeccable,” he wrote on the campaign application at the time. “I have a good reputation.” None of the companies he was affiliated with have commented on his actions, to his ex-wife’s dismay.

“They should say something,” she insists. “But they still support him because maybe they think they have a future somehow with donations.”

Once it was discovered that Arbor had left the country, he was immediately held in contempt for defying the court-ordered divorce payment order. Soon after, he was held in contempt again—this time for not paying court-ordered child support to a different woman he impregnated during a secret affair, according to the arrest warrant issued for him at the time.

Vigilante was not surprised. “I saw a manipulator. I saw someone deceitful. Someone with no moral compass,” she says. “Someone who was a good storyteller and who always fudged the truth. He had a terrific way of convincing people that he was telling the truth. You had to do what he requested or he made your life a living hell.”

Overseas, he spent his time between Rome and Lugano, with frequent trips to his ancestral home in Gravina, Puglia, in southern Italy. There he funded the expensive renovation of an ancient clocktower after connecting with his relative Renzo Arbore, a popular Italian showman who uses the original family name spelling. (The final ‘e’ in Arbore was dropped when Arbor's parents emigrated to America in the early 1900s.)

Reached by phone, Arbore told The Daily Beast that his American uncle is a "good man" who was being taken advantage of by a "greedy woman" who only wanted his money. Arbore met his American relative and Vigilante when he played a gig in Chicago in 2009. "I never liked her," he said. "You could tell she was evil."

Arbor seemed destined to live out a comfortable expat retirement in Europe with his alleged fortunes. But Vigilante had her own plan.

She tipped off the feds that her ex-husband had always kept secret investments in foreign accounts—up to $55 million by some tallies—leading to a massive tax evasion crisis for him. He was then forced to admit through his lawyers that he had indeed evaded taxes for more than 30 years as his overseas investments grew. He had to pay hefty fines and back-taxes to avoid losing his extensive property portfolio in the United States.

Arbor called Vigilante's disclosure “an attempt at blackmail” but did not come back to the United States to settle his affairs. Instead, he reportedly shuttled between between Europe and Mexico, where the Sun-Times says he invested in property for the children from his previous marriage.

But then, last May, the multimillionaire took a calculated risk and flew home to America to attend the university graduation of one of his grandchildren in Boston, presumably hoping his quick trip would be under the radar. But it wasn't. Vigilante, who obsessed over her ex-husband's every move, says she alerted the authorities that he might return. He was arrested as he attempted to board a flight back to Rome and then extradited to Illinois, where he has been since, in the hospital wing of a penitentiary.

Vigilante claims that her husband originally escaped to Europe to avoid paying her the settlement the courts ruled she rightly deserves. Now, she says he is purposely not posting $1.4 million bail to avoid paying her her due. She said her lawyers have made several offers to reduce the settlement but thinks Arbor would rather die in jail than give her a penny.

“He holds the keys to his jail cell,” she says. “This is a man who can pay but simply won’t.”

Arbor argues that he is flat broke and can't post bond. He claims he lost $14 million in a Portuguese bank that went bust and another $2 million in an investment scheme in Ukraine. What little he claims he has left—around $5 million—he says is stuck in a trust fund in Switzerland he claims he can't access because he's in jail.

Vigilante says her lawyers have tried to access that money, but Arbor won't share the passwords that would release the funds. In his Sun-Times interview, Arbor insisted he has no control over his destiny.

“I’ve had many lawyers, one after another after another, and nobody can have me liberated. So I’m kind of doomed, I guess,” he said.

Arbor's lawyers have argued that Judge Myron Mackoff should let the old man out and keep him on electronic surveillance. Arbor is weak and in ill health, they say, and by keeping him in prison, the judge is essentially giving him a death sentence.

“He hasn't committed a crime; he just owes money,” Rosenfeld told the judge in a heated debate at his bail hearing, according to court documents and press reports. “He has no ability to pay.”

The judge clearly does not believe it and contends that Arbor is a flight risk even though he has relinquished his American and Italian passports. The judge says Arbor could still make an escape through his considerable resources and connections.

“Nobody is above the law,” Mackoff said at a December hearing on the request for house arrest, which was denied.

Arbor argues the case has been unfairly stacked against him from the start. He said he and Vigilante never lived together “full time” during their lengthy marriage, and he alleges she broke into his Chicago penthouse and raided his wall safe, taking more than $400,000 worth of gold nuggets and cash in various foreign currencies that was meant as his emergency fund. He says she also failed to take proper care of him when he underwent cancer treatment and that she bought property in his name without his consent.

His lawyers also say that he left the country and transferred the money to foreign accounts before the divorce order was final—meaning it wasn’t illegal at the time.

Vigilante instead says he is the devil incarnate. “I don't want Pat to rot in jail,” she told Sun-Times columnist Mark Brown. “But I find his behavior replicates the devil.”

Brown, who has covered this case from the start, says he believes that while this battle is about the money, the resulting chaos is a war of wills.

“As I told Mr. Arbor when he said he’s been told she wants him to rot in jail, I believe she wants the money she thinks she is due—and sees as necessary for her future financial security,” Brown told The Daily Beast.

“I believe he thinks she has received more money from him than she deserves and is determined to keep her from getting more. I think it’s a pretty commonplace divorce scenario spiced up by the fact that Mr. Arbor, once a person of considerable stature in Chicago, chose to become a fugitive in his effort to win.”

Vigilante, who runs a real estate company in Florida, risks never collecting her divorce payments.

If Arbor dies in jail, which is increasingly likely given his poor health and advanced age, his entire estate goes to his children from his previous marriage. Death in prison seems the only guarantee Arbor has that his ex-wife never sees her share of his fortune.

“My Christmas wish is that he would come to his senses, make a fair and reasonable offer and settle the case with me so he can get out of jail,” she says. “But I think he feels that he has to win, even if it kills him.”