Did a former employee drop a dime on Cheryl Womack?

Cheryl Womack is running out of time if she’s going to make her visit to the Cayman Islands for a New Year’s Eve party.

Womack wants to fly to the Caribbean tax haven so she can ring in 2014 with that island’s politicians. The Mission Hills businesswoman thinks her appearance at the New Year’s Eve gathering and other meetings in January will help grease the skids for an environmental project she’s trying to get off the ground in the Cayman Islands. Her project purports to turn municipal garbage otherwise headed to a landfill into ash and other things.

But Womack has a pesky problem – the well-known local businesswoman, who sold her trucking insurance company for $35 million in 2002, lost her passport when federal officials indicted her earlier in December for an alleged $7 million tax-fraud scheme. Her alleged crimes, which include charges that she lied to federal investigators, center heavily around her business dealings in the Cayman Islands.

No passport, no flight to the Caymans.

Womack’s attorney worked on Christmas Eve writing an emergency motion to try and get his client’s passport back in her hands so she can fly to the Caymans in January and make another business trip to India in February. That motion came one day after a federal judge agreed with federal prosecutors that Womack poses too much of a flight risk, despite offering up as collateral her Mission Hills home (appraised at $5.5 million) and the surrender value of her life-insurance policy (nearly $800,000).

In court filings, Womack’s attorney says the government’s investigation against his client started no later than the date that a woman named Brandy Wheeler pleaded guilty in 2008 for embezzling more than $1 million from a holding company that Womack runs. Wheeler could have gotten up to 30 years in prison for her crimes, but instead got only one year and one day, along with restitution, when she received her sentence in 2010.

That was after federal prosecutors asked a judge for leniency in Wheeler’s sentence. U.S. District Court Judge Fernando Gaitan said at Wheeler’s August 3, 2010, sentencing hearing that she had to go to prison for at least a little while, despite whatever help she had given to prosecutors to reduce her punishment.

“I think some time is required for this conduct because it’s serious conduct, notwithstanding what may happen to your boss as a consequence of her conduct,” Gaitan said.

While Gaitan didn’t name names, he may have been speaking about Womack. At least that’s what Womack’s attorney thinks.

“It was thus clear, at the time of Ms. Wheeler’s plea agreement, that she needed to provide ‘information’ sufficient to get someone indicted for something in order to substantially reduce the jail time she was facing for her admitted theft,” says Womack’s New York attorney Michael Levine in a court filing. “It was equally obvious that the only person who would be attractive to the government in that regard was her boss, Ms. Womack.”

Levine goes on to say that Womack knew the feds were on her trail since 2008, all the while making foreign business trips and always returning to Kansas City. On October 18, Womack and her attorneys watched a PowerPoint presentation given by a federal prosecutor that explained the evidence the feds had gathered about Womack’s alleged tax-dodging ways. The prosecutor made a deal (the details of which aren’t specified in the public record), adding that if Womack didn’t take it, she would be indicted by the end of 2013.

Womack didn’t take the offer and was charged on December 11, four days before the statute of limitations expired on some of the counts against her. She gave up her passport to the feds five days after her indictment. That proves to her attorney that Womack is not a flight risk; she had five days to grab a flight and hightail it out of the country and didn’t.

The feds, however, weren’t impressed by the offer of her home and life insurance as collateral. They say Womack’s home, despite its $5.5 million appraisal, would probably fetch less in a U.S. Marshals auction. They also think Womack may have evaded $10 million in taxes, up from their previous allegation that it was $7 million.

Womack’s attorney is taking his chances with the Eighth Circuit Court of Appeals to try to get Womack’s passport back. As of Monday morning, the court has not made a decision.