He also acknowledged a shortfall of 43 43 million in federal taxes from 2005 to 2014 and agreed to pay about million 140 million in taxes and fines.
He will pay US$139 million in taxes and penalties, and will abandon a US$182 protective refund claim and pay interest as part of the deal.
Prosecutors claimed that Brockman used a family charitable trust and offshore firms based in Bermuda and Nevis, as well as bank accounts in Bermuda, Switzerland and the British Virgin Islands (BVI), over a 20-year period to hide income from private-equity investments from the Internal Revenue Service (IRS), the United States tax authority.
A Bloomberg story said, "Robert T. Brockman, a Houston software tycoon, was charged with using a web of Caribbean entities to hide $2 billion in income in what prosecutors called the largest US tax case ever against an individual".
Brockman, a resident of Houston and Pitkin County, Colo., is chairman and CEO of Reynolds and Reynolds, a 4,300-employee company near Dayton, Ohio, that sells accounting, sales and management software to auto dealerships.
A spokeswoman for Reynolds and Reynolds told the New York Times that the company "is not alleged to have engaged in any wrongdoing, and we are confident in the integrity and strength of our business", and noted that Brockman's actions occurred "outside of his professional responsibilities".
Brockman, who lives in Houston and Pitkin County, Colo., is a Marine veteran who started out in marketing at Ford Motor Company. He later worked as a salesman at IBM in 1970, before Reynolds and Reynolds acquired Universal Computer Services, which led the company in 2006.
A spokesman for Reynolds and Reynolds said ਨਿ.
Brockman also "engaged in multiple instances of obstructive conduct", including directing an associate to destroy documents and electronic media using shredders and hammers, according to the indictment.
"These allegations should disgust every American taxpayer as well because the law applies to all of us when it comes to taxes and paying our fair share", Mr. James Lee, chief of criminal investigations at the IRS, said the charges "disgusted me". However, the indictment charges that he conspired over two decades to secretly maintain "complete" control over trust assets while failing to pay capital gains and income taxes. The misconduct lasted from 1999 to 2019, authorities said.
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"Complexity will not hide crime from law enforcement".
The indictment also alleges that Brockman took measures such as asking employees to backdate records and using encrypted communications to hide the alleged scheme.
To keep up the scheme, Brockman used secret, encrypted email systems to coordinate with offshore money handlers, according to the indictment.
The charges also included allegations that between 2008 and 2010, Brockman lied to investors and allegedly bilked them out of almost $68 million. Brockman is the sole investor in Vista's first private equity fund.
The CEO of the private-equity firm Vista Equity Partners will admit misconduct but will not be prosecuted, sources told Bloomberg.
Billionaire Robert Smith is likely best known for his charitable stunts, such as vowing to pay off the debts of Morehouse College's entire graduating class a year ago. This amounted to an estimated $40 million.
Mr. Smith agreed to cooperate with federal prosecutors against Mr.
Mr. Smith's cooperation with the government "put him on a path away from indictment", Mr. Anderson said. Anderson said the agreement showed that "it is never too late to do the right thing".
Smith, 57, avoided prosecution by agreeing to co-operate against Brockman.
Smith faced a related four-year criminal tax inquiry involving about $200 million that moved through Brockman-linked offshore structures. He has agreed to cooperate with ongoing federal investigations, to forfeit tax breaks on $182 million in charitable contributions, and to pay nearly $140 million in fines.