Sam Wyly was born in 1934 to parents Flora and Charles Wyly, Sr. of Lake Providence, Louisiana. His family descended from a long line of Presbyterian and Episcopalian ministers, college founders, and teachers. Wyly’s paternal grandfather was a lawyer who managed plantation assets and helped poor Black convicts get paroled from Angola Prison. His maternal grandfather was a doctor.

From 1960 to 1976, Wyly was married to Rosemary Acton. In 1978, he married Victoria L. Steele.

After Michigan, Wyly went to Air Force Boot Camp in San Antonio and to Dallas for a job with IBM. He and Ross Perot were classmates at IBM’s education center. Three and a half years later, Wyly left IBM for Honeywell, establishing their computer business in Dallas, Ft. Worth, and Oklahoma. When Honeywell rejected his plan for a new technology computing center to replace the obsolete Univac at SMU, he quit to do it himself. Wyly started his own company in 1963.

In 1968, Sam Wyly was a delegate to the Republican Convention at the request of Chuck Percy, an Illinois Senator and former CEO who he met at a “Young Presidents’” event. After Percy lost the nomination, Wyly became Chairman for the “Nixon For President” campaign in Texas. It was the first time that Republican presidential money had matched that of Democrats in Texas, which had been part of the “Democratic Solid South” since the Civil War.

In 1968, he set up the Sam Wyly Foundation to help black business owners.

In 1979, Wyly settled Securities and Exchange Commission (SEC) charges that he made undisclosed payments to associates to buy up company bonds as part of a plan to stave off bankruptcy for University Computing after the $100 million Datran loss. He settled without acknowledging any wrongdoing.

In 1992, his friends Ross Perot and George H. W. Bush both ran for president. Perot got 20 percent, but with two Texans on the ballot, “another Bubba” from Texarkana—Bill Clinton—won the White House. Perot, Clinton, and Wyly all grew up less than 100 miles from each other in Louisiana, Arkansas and Texas.

In August 2006, the Dallas Morning News reported that Sam and Charles Wyly were again under investigation by the SEC, a grand jury in Dallas and a grand jury in New York, regarding their use of potentially illegal offshore tax shelters. No criminal charges were made by either Grand Jury. Senate investigators allege that the Wyly brothers used the offshore trusts to buy $30 million worth of artwork, jewelry, furniture and other items for their personal use. The Wyly brothers denied any wrongdoing, and stated that they just followed the advice of their lawyers and CPAs.

Cheryl and Sam Wyly purchased Explore Booksellers and Bistro in January 2007, ending concern by Aspen, Colorado locals that the only book store would be converted into condos.

In March 2007, commenting on the purchase of a local bookstore by Wyly and his wife Cheryl, the Aspen Times noted that the Wyly family “has been known not only for its philanthropic efforts, but also its large contributions to conservative political campaigns and candidates.” Sam backed George H. W. Bush for president in 1980 and 1988. Sam backed George W. Bush’s run for Congress in West Texas in 1978, for governor in 1994, and president in 2000 and 2004.

Wyly’s memoir, 1,000 Dollars & an Idea, was published in September 2008. His last book was The Immigrant Spirit: How Newcomers Enrich America, and his May 2018 book is Dallas Got It Right!, co-authored with Laurie Matthews and Andrew Wyly.

On July 29, 2010, the SEC charged Charles and Sam Wyly with fraud for violating federal securities laws governing ownership and trading of securities by corporate insiders. Sam was surprised with the charges, because historically such cases were brought when public investors lost money. In these companies— Michaels, Sterling Software, and Sterling Commerce—public investors had profits well above the averages.

His illustrated biography, Beyond Tallulah, How Sam Wyly Became America’s Boldest Big-Time Entrepreneur, by Dennis Hamilton (Melcher Media) was published in 2011. Hamilton began writing about Sam in software journals in the 1970s.

Wyly and his brother Charles, older by a year, were close all their life. They played high school football, attended Louisiana Tech University, and joined Pi Kappa Alpha fraternity together. They worked together in a large number of businesses that they either owned or ran. Charles was killed in a car accident in Aspen’s Roaring Fork Valley in 2011.

Sam and his son Andrew published their book, Texas Got It Right!, in October 2012. The book claims to explain why California, New York, and the Rust Belt states are losing jobs to Texas and the Southern and Rocky Mountain states.

The Wyly brothers made an immense fortune for themselves, employees and stockholders through investments in Michaels Stores and several software companies. They had been accused of avoiding their tax obligations by transferring stock options in Michaels and Sterling Software Inc. to offshore trusts after receiving advice from a lawyer who promoted foreign trusts as a method of asset protection and tax deferral. On May 12, 2014, a civil jury in New York found the Wyly brothers liable on counts for use of offshore trusts. On July 11, 2014, Sam Wyly and his late brother Charles, were found not liable for insider trading by a U.S. Judge in New York.

On October 19, 2014 Sam Wyly filed for Chapter 11 bankruptcy, having lost one of the cases brought by the SEC, and wanting to force the IRS to “put up or shut up” about any taxes he owed related to his family’s offshore trusts. The IRS had been auditing his tax returns for a decade without ever telling him whether he owed any additional taxes.

In 2015, Wyly founded WylyBooks Company, a nonprofit to fund his storytelling about America’s history and future.

In April 2015, the Internal Revenue Service filed claims amounting to $3.2 billion for income taxes, interest and penalties against Wyly and the estate of his late brother. His lawyer called the IRS claims “unfair and absurd.” The largest tax claim ever imposed against an individual. Wyly jokes that this was an IRS “billing error.” “They sent us Exxon’s tax bill by mistake. Exxon’s headquarters is a few miles from my house.”

In 2016, Wyly settled with the SEC, entering into a settlement agreement under which he agreed to pay $198.1 million. “This is a significant step towards resolving Mr. Wyly’s disputes with the government and allowing him to exit from bankruptcy,” said Jim Lee, a lawyer at Vinson & Elkins.

In June 2016, the Court ordered Wyly to pay $1.1 billion in taxes, interest and penalties. The IRS moved to collect from the offshore trusts that had been set up by Wyly.

Wyly has six adult children, Evan, twins Laurie and Lisa, Kelly, Andrew, and Christiana. In April 2018, Christiana Wyly, an environmental activist, married entrepreneur Kimbal Musk.