The Secrets of the Hopewell Box: Stolen Elections, Southern Politics, and a City's Coming of Age

An Enemy Within

James D. Squires 210 lege of Trial Lawyers, one of the highest honors in American jurisprudence, with membership limited to 1 percent of the lawyers in any state. He had to be, Osborn repeatedly told his friends and family, “one of the luckiest men in the entire world.” But they in turn insisted that Tommy Osborn was just one smart sonofabitch. Everybody turned out to be wrong on both counts. An Enemy Within IfTommyOsbornreallywantedtoridealongshotlikeGallahadion, he picked the right horse in James R. Hoffa. The New Frontier was clearly not big enough for the arrogant, abrasive boss of the nation’s Teamsters union, the man who had campaigned personally against John Kennedy and publicly upbraided Bobby as “a young, dimwitted, curly headed smart aleck.” Hoffa’s weight with union voters had been credited with tipping Ohio for a grateful Vice President Richard Nixon, who in turn had intervened with the Justice Department to delay a planned indictment of Hoffa in Florida until after the election. Had Nixon won, Hoffa expected the case to be dropped. But from the minute Kennedy was sworn in, the volatile union leader became the Justice Department’s number-one target. The tangle of personal friendships and resulting political clout that had been employed on the issue of reapportionment was rooted in the issue of Teamster union violence in Tennessee, and the two soon became inextricable, tangled in both the political life of Nashville and the personal life of Tommy Osborn. The reasons for going after Hoffa and the way best to do it had been the basis for Bobby Kennedy’s best-selling book, The Enemy Within, documenting for the nation that both Hoffa and the Teamsters union were controlled by organized crime. Written in ten An Enemy Within The Secrets of the Hopewell Box 211 weeks at Kennedy’s Virginia home during the summer of 1959 by Kennedy and his Teamster expert from Nashville, John Seigenthaler, the book’s publication was timed to coincide with John Kennedy’s campaign. Such timely meshing of moral crusade and personal agenda was one of the most potent and oftenemployed of the Kennedy political weapons and the one used regularly against Hoffa. Much of the information in the book had been gathered during a Senate investigation ofTeamster activities nationwide,which included the bribing of a Tennessee judge who was subsequently impeached. Seigenthaler had reported the story originally, and young John J. Hooker, Jr., had been involved as assistant to the special prosecutor in the impeachment case, Osborn’s mentor Jack Norman. Eventually, the judge’s impeachment trial became an important source of information for some widely publicized congressional hearings for which Robert Kennedy was chief counsel. This led to Seigenthaler’s friendship with Kennedy and to his being offered a job in the Justice Department. Among the first acts of the new attorney general was recruitment of a group of young lawyers who became known as “the Hoffa unit.” And among the cases the Hoffa unit were trying to build against the burly, hot-tempered union boss was one with a Nashville connection. During the fifties Hoffa and one of his union vice-presidents had collected more than $1 million from a trucking company, Test Fleet Corporation, that they had secretly set up in Nashville, which because of its geographic location had become the trucking center of the Southeast and one of the union’s fastest-growing membership areas. The Nashville case against Hoffa was not a strong one.The crime involved was only a misdemeanor, a violation of the Taft-Hartley Act, which prohibits union officials from receiving payments other than wages from their unions. Conviction carried a penalty of only one year in prison and a ten-thousand-dollar fine. The case was so weak in fact that John J. Hooker, Jr., whom Kennedy had invited to evaluate all potential legal actions against Hoffa, had recommended James D. Squires 212 against bringing it. But Hooker didn’t think much of the mail fraud case in Florida either, which had already been dismissed once, or a similar one that could be brought in Chicago. “You won’t win any of them,” Hooker told Kennedy, to his chagrin. But Kennedy believed strongly in persistent prosecution of Hoffa on any charge, no matter how insignificant. Three times his slippery enemy had been tried by the federal government, and three times he had gotten off. Each time his main...