With plea deal now off the table, it looks like Cheryl Womack may head to trial after all

On January 14, federal prosecutors told attorneys representing Mission Hills businesswoman Cheryl Womack that she had until the end of the day to take their plea offer or leave it.

It had been a couple of months since Womack seemed ready to accept some kind of fate offered up by the government. A federal grand jury indicted Womack in late 2013 on numerous allegations that read like she evaded taxes; the actual charges mostly deal with claims that she had misled authorities about the activities of several offshore businesses and bank accounts, all falling short of actual tax-evasion charges.

Womack was a self-made millionaire, toiling in a low-pay insurance job before she started the National Association of Independent Truckers, which she later sold for millions. Since then, she has been involved in a melange of different business and philanthropic pursuits.

Womack scheduled a change-of-plea hearing on November 12, 2014. But just days before that, Womack wanted to call off the hearing. She had learned that federal investigators withheld what her attorneys thought was a key piece of evidence. In criminal proceedings, prosecutors typically have to hand over all the evidence they plan to use against a defendant before a trial starts. That includes any evidence that the government has that could help the defendant’s case.

One of the missing pieces of evidence in Womack’s was what’s called a Tax Information Exchange Agreement. A TIEA can be roughly described as a treaty between two countries that pledges mutual cooperation during investigations of possibly illegal tax schemes.

Womack’s attorneys wanted to see the federal government’s TIEA application to investigate Womack with the Cayman Islands, the Caribbean tax haven where prosecutors believed Womack directed her income from things like high-priced wine auctions.

What comes next is what looks on the outside to be a strange game of hide-and-go-seek carried out by the authorities. The government, according to Womack’s attorneys, said earlier in 2014 that it had already given her legal team the TIEA, and if they wanted to find it, they had to look closer through thousands of pages of evidence.

When Womack’s attorneys still couldn’t find it, the feds said they’d get a copy from the Internal Revenue Service. Then suddenly the IRS couldn’t find it. When the feds finally tracked it down, they wouldn’t hand it over unless Womack and her attorneys agreed to a gag order keeping anyone from discussing what the document revealed. Federal prosecutors have argued that the document contains sensitive national-security information.

Long story short, Womack’s attorneys got to look at the TIEA but couldn’t take a copy with them. It’s unclear what information they learned from it, but her attorneys weren’t willing to let Womack plea to anything without a full picture of what evidence the government had against her.

Womack’s attorneys said they’ve been receiving evidence in drips and drabs, but that by January 14 they still didn’t have it all. By the end of that day, the plea offer expired.

Now Womack looks like she may head for a trial. In a motion filed in federal court last week, Womack’s attorneys say they will be ready for a November 2015 trial. A judge hasn’t approved that date, but federal prosecutors have agreed that a November trial works for them, too.