In the late 1950s, a young lawyer from Boston acting as counsel to a Senate subcommittee investigating organized crime’s involvement in unions squared off against the head of the Teamsters. The meeting would prove the first of many as Robert Kennedy sat across from Jimmy Hoffa, the two as compatible as water and oil. Jimmy Hoffa was one of the most interrogated men in U.S. history. Having used street tactics to rise from the streets of Detroit to the head of the Teamsters, Hoffa was enormously popular with union members whose salaries he had tripled in a matter of ten years.
Along the way to building his success with the Teamsters, Hoffa also won widespread respect among the trucking-industry officials with whom he dealt. So, too, he became involved with a host of unsavory organized crime members like Tony Provenzano from New Jersey and Johnny Dio in New York. On the other side of the table sat Boston lawyer Robert F. Kennedy, a man who had already labeled Hoffa the most powerful man in the country after the president, one who union represented a “conspiracy of evil”. The two men openly exhibited animosity toward one another, with Kennedy grilling Hoffa about his connections to organized crime. Hoffa would walk away from this investigation relatively unscathed, but he earned himself a powerful adversary in the form of Robert F. Kennedy.
With the 1960 election of John F. Kennedy, Robert F. Kennedy was appointed Attorney General of the U.S. Perhaps there could not have been two more different characters than those represented by Kennedy and Hoffa. Hoffa had fought his way to the top of the Teamster with fists and hardball negotiating tactics that often included violence from union members. Largely uneducated and poor, Hoffa in his trademark cheap black suit and white socks with black shoes could not have stood more in contrast to the Ivy league, wealthy, Kennedy in his impeccably tailored suits and tasseled loafer...