The Kennedy Heirs: John, Caroline, and the New Generation by J. Randy Taraborrelli

Author:J. Randy Taraborrelli
Language: eng
Format: epub
Publisher: St. Martin's Press

John’s Political Musings

Because she already wanted more of his time, no doubt Carolyn would have also been concerned about John’s latest curiosity: he was contemplating running for the United States Senate in 2000, for Daniel Patrick Moynihan’s seat.

“I think I’m ready to make the leap,” John told his close friend Gary Ginsberg. To test the waters, Ginsberg met with Republican strategist Roger Ailes, who at the time was building Fox News, in order to evaluate John’s viability as a candidate. Though decidedly on the other side of the aisle, Ailes was someone who always had his finger on the pulse of current-day politics and, Ginsberg felt, could be trusted to venture an informed opinion—and then to keep that opinion to himself and not go to the press with it. The two had lunch to discuss John’s possible candidacy, which in the end Ailes felt was feasible. When Gary reported this good news back to John, he was heartened by Roger’s enthusiasm. It was in line with what other political strategists and reporters on the beat had told him.

“Most people felt sure that John could win that Senate seat should he go for it, and that there was no reason he shouldn’t at least try,” said family attorney Benedict F. Fitzgerald Jr. “I think a concern of John’s, though, was that Hillary Clinton was making overtures for that seat after she and her husband were out of office. John didn’t want to run against her.”

Besides the fact that the Clintons and the Kennedys were close, John was sure he wouldn’t win against Hillary. Not only that, he felt bad for her considering what was going on at the time with the Monica Lewinsky scandal. However, John’s cousin Kathleen urged him to not allow too many side issues to influence his decisions going forward in politics. “There will always be one thing or another,” she told him, according to one account, “and you have to take some things into consideration, but not everything.” In November 1998, Kathleen would win another term as lieutenant governor of Maryland, so John had a lot of respect and appreciation for her point of view. “I’m wishy-washy, I know,” he told her. “I need to be more like you.” She countered with “No. Be more like you, John.”

Key in the equation as to whether John should run for office would be, of course, his wife’s attitude about it. How would Carolyn ever be able to adjust to life as a politician’s wife? She was still having trouble reconciling things as just the wife of someone famous. Add politics to John’s celebrity and there was no telling how it might impact her life.

Still, there was a lot of optimism about John’s future. “There was never any doubt in my mind that John planned to run for the U.S. Senate in the next decade,” said his friend the noted historian Douglas Brinkley. Or … maybe something else? “John had talked a lot about possibly running for governor in 2002,” confirmed RoseMarie Terenzio, “and I think he would have ended up doing that.

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