Winston was 68 years old, 5’6”, slightly hunched, with pale skin and a rapid fire manner of delivery. I first met him when he was transferred to Marion from Butner Medical Center after having surprised (and disappointed) many people in the Bureau of Prisons by surviving his third round of cancer.
He was not the type of person to suffer fools, and would respond to any inquiry about him or his past by asking a series of questions designed to determine, in his mind, whether the subject of his interrogation was worth spending time with. As he would later explain to me, after 20 years in federal prison, he didn’t think he had time to waste on inmates who placed no value on time simply because it was in such supply.
Winston was the founder and CEO of a hugely successful property and casualty insurance company in Illinois. He built his 
company by specializing in hard to insure properties and businesses and collecting what was then an enormous amount of data about his clients so he could both better design policies and help them to reduce losses. The combination of his insuring higher-risk (and thus, higher premium paying), clients and diligent underwriting made him wealthy by the time he was 40.
As often happens to successful men, he grew bored and decided to tackle new challenges. Some state laws at the time prohibited companies like his from competing across multiple jurisdictions. There were also other laws in the state of … Read the rest