Robert Brockman, the former CEO of Reynolds & Reynolds Co., a maker of software for auto dealers, pleaded not guilty.
Smith used foreign trusts, corporations and bank accounts to cheat the IRS, prosecutors charge.
Robert Brockman, 79, used a family charitable trust based in Bermuda and other offshore entities to hide assets.
An ongoing investigation may have uncovered one of the largest tax frauds in U.S. history.
Authorities want to know whether he failed to pay taxes on $200 million moving in offshore structures.
With travel virtually shut down across the U.S., hotels have emptied out as trips have been put on hold.
A financial institution in Central America is suspected of helping global customers evade taxes and launder money.
The site encouraged users to upload videos and hundreds of thousands of illicit images.
The suits say Epstein relied on associates and employees to orchestrate illicit encounters with girls and young women.
By placing all of his assets in a trust, Epstein could shield their distribution from the public.