[1] After LeBow acquired the cigarette manufacturer Liggett Group in 1986, the company became involved in anti-tobacco lawsuits culminating in the 1998 Tobacco Master Settlement Agreement.

LeBow's father, Martin, was a life insurance salesman and his mother, Suara (née Weiss), was a teacher.

[2][3][4] He graduated from West Philadelphia High School,[4] and in 1960 earned a degree in electrical engineering from Drexel University.

Before completing his degree, LeBow left Princeton and joined the army where he installed early data systems at the Pentagon.

[4] LeBow's first foray into business occurred in the 1960s, when he started a computer company to continue his Pentagon project.

The company, then renamed New Valley LLC, eventually filed for bankruptcy but was able to pay its bondholders in full via asset sales.

Liggett later sold its remaining interest in Western Union Financial Services Inc for $1.2 billion, earning it a $300 million profit.

[19] In 1996, while under his leadership, Liggett Group broke ranks with the rest of the US tobacco industry, including Philip Morris, Brown and Williamson, RJR Nabisco, Loews and Lorillard, when he announced that Liggett would settle the Medicaid tobacco suits brought by forty state attorneys general.

[22] LeBow was honored with a proclamation by Florida governor Lawton Chiles for his "invaluable assistance" in helping the state achieve its $11.3 billion settlement with the tobacco industry.

[35] In 2009, LeBow made a $10,000 campaign contribution to Manhattan District Attorney candidate Leslie Crocker Snyder, whose law firm – Kasowitz, Benson, Torres & Friedman – had represented the Liggett Group in smoking and health litigation since 1996.

[10] LeBow was first married to Geraldine Cosher[38] whom he met while they were college students (he was at Drexel and she attended Temple University).