Wyly's recent wealth stems from ownership stakes from Sterling Software and Michael's, an American art supply store.

Wyly's paternal grandfather was a lawyer who managed plantation assets and helped poor Black convicts get paroled from Angola Prison.

[3] He began working at an early age, helping his parents publish a weekly newspaper titled The Delhi Dispatch in Richland Parish.

He sold advertising, wrote stories, sent telegrams for oil and gas workers, folded and addressed the finished papers, delivered daily newspapers from the bus stop on Highway 80, and cleaned the printing presses.

Three and a half years later, Wyly left IBM for Honeywell, establishing their computer business in Dallas, Fort Worth, and Oklahoma.

[8] When Honeywell rejected his plan for a new technology computing center to replace the obsolete Univac at Southern Methodist University, he quit.

In 1968 he acquired Gulf Insurance[12] to help fund his ambition of a nationwide digital network to compete with AT&T, then the national telephone monopoly.

[17] His illustrated biography, Beyond Tallulah, How Sam Wyly Became America's Boldest Big-Time Entrepreneur, by Dennis Hamilton (Melcher Media) was published in 2011.

In 1968, 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.

[5] With his brother Charles, he funded the 16-story Tower of Learning at Louisiana Tech, designed by the Bastrop architect Hugh G. Parker Jr.

[32] 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.

A grand jury was convened in both Dallas and in New York,[34] to collect evidence regarding their use of potentially illegal offshore tax shelters.

[34] In the past the Wyly brothers have been accused of avoiding their tax obligations by transferring stock options in Michaels and Sterling Software Inc however were never criminally indicted.

[2] While the SEC was pursuing Wyly in federal court, New York State launched a civil lawsuit against him for the misuse of offshore trusts.

[41] The investigation by the SEC attracted the attention of the Internal Revenue Service as it was believed Wyly failed to pay federal taxes on his assets.

The IRS opened a formal inquiry that same year and began to pursue Wyly on tax evasion charges.

[42] In court, Wyly defended himself by claiming that his accountants were responsible for the assets in the Isle of Man and that he had no knowledge or involvement in where his money was going.

[45][46] The SEC and IRS prosecutions coupled with the civil lawsuits from New York impacted the financial situation of the Wyly's substantially, and he declared bankruptcy in 2014.

They both played high school football, attended Louisiana Tech University, and joined Pi Kappa Alpha fraternity together.

[55] Between 2013 and 2015, Christiana was in a same-sex civil partnership with Skin, lead singer of British rock group Skunk Anansie.