Looks like Cheryl Womack may be pleading guilty in her criminal case

Mission Hills businesswoman Cheryl Womack is scheduled to appear in federal court in Kansas City on November 12 for a change of plea hearing in her criminal case.

Womack had earlier entered a not guilty plea to charges of avoiding income taxes and lying to investigators.

(Update, 9:03 p.m)

It’s not clear what Womack may plead to next month if the hearing occurs as scheduled.

“With the exception of one answer she gave under oath on an unrelated matter, the allegations in the indictment are absolutely not true,” says her attorney, Cynthia Cordes, in an email to The Pitch. “The statement had to do with her memory about the year a company started.”

A grand jury indicted Womack on December 12, 2013, of setting up a network of off-shore bank accounts, trusts and business entities to carry out what was then described as a $7 million tax-avoidance scheme. Federal prosecutors later upped that estimate to $10 million worth of evaded taxes.

Womack made a fortune in 2002 when she sold the National Association of Independent Truckers, a liability insurer for truck drivers, for $35 million. Womack didn’t just live off the bounty that that NAIT sale afforded her. She spent the following years as an entrepreneur, business consultant and philanthropist.

She donated $2 million to Kansas Athletics Inc., so the Kansas Jayhawks softball team would have a better stadium for its home games in Lawrence. Arrocha Ballpark was named after Womack’s father, Demostentes Arrocha, a Panamanian immigrant to the United States who raised Womack and her 10 siblings in Wyandotte County.

Womack was a 1975 graduate of the University of Kansas and stayed on as a booster for its athletics department. She was also an advocate for the department’s reform when several employees got busted for a ticket embezzling scheme in 2010.

Womack is still listed as a director for basketball coach Bill Self’s charity, Assists Foundation.

Womack also used her money to purchase millions of dollars’ worth of expensive wines. Her collection grew so large that she decided to auction part of it off in 2008, a sale that fetched $1.6 million.

Womack, according to court records the grand jury indictment, had those proceeds transferred to a company that she established in the Cayman Islands, which later wired money to her Missouri Bank account in Kansas City. None of this was reported on her income taxes, federal investigators said. Nor, they added, were a series of other transactions and business holdings that allowed her to skip on $10 million that she would normally owe to the Internal Revenue Service.

The 2013 indictment probably didn’t come as a surprise to Womack. Investigators pursued Womack as far back as 2008, shortly after her wine auction. The FBI questioned her about a money trail leading to and from the Caymans, which Womack couched as an arm’s-length transaction between herself and investors (prosecutors alleged that she controlled the companies and bank accounts involved).

People close to Womack also felt law enforcement’s heat. Womack testified before federal authorities in 2009, who at that time were after a tax preparer who had a long history of creating legally dubious tax shelters for his clients. Allen Davidson, known as Dr. Poof for his skill in making tax liabilities disappear into thin air, worked for Womack’s insurance company until it sold, and then continued on as the tax adviser for a holding company Womack put together.

The grand jury believed that Womack tried to throw investigators off her trail during that 2009 testimony with misleading or false statements about her own activities.

An employee of Womack’s VCW Holdings, Brandy Wheeler, got prosecuted in 2009 for embezzling $1.1 million from the company. When Wheeler got a lighter-than-expected prison sentence, it became clear that she was cooperating with the feds on a bigger case against someone else.

That someone else was Womack.

Womack could change her mind between now and the scheduled November 12 change of plea hearing.

But because she entered a “not guilty” plea last year, the only thing she could change it to is “guilty.”