People always screw up the timeline here. JFK Jr. is even on those asinine "Clinton Death Watch" lists. Ridiculous. Dude died in
July 1999.
Charlie Rangel and others had already approached Hillary about the Senate in
late '98.
She waited until after the impeachment trial,
February 16, 1999, to announce.
http://www.people.com/article/jfk-jr-run-president-interest-politics-before-death
"He had been thinking about running for the N.Y. Senate seat – he even had meetings about it that spring – but by July had concluded he would focus his attention on running for governor of N.Y. in 2003.
"By temperament and interest, John, I think, realized he was far more suited to being a governor than a legislator. He knew from running George that he could be an inspiring, strong chief executive of a state, setting the tone for government and successfully running a complex operation.
Running George gave him a taste for executive power. His shot was the Governor's race. That's what Teddy was pushing him into and he was apparently ready to pull the trigger on it before his death....
His loyal assistant at George, RoseMarie Terenzio, recounts a surprising conversation she had with her boss after New York Senator Al D'Amato – a Republican – told John he should run for mayor of New York City.
At the time, John laughed it off. But afterward, she asked him if he’d ever consider it.
"He said 'Well, Rosie, how many mayors do you know that become President?' " recounts Terenzio. "I was so shocked I didn't say anything. Then he smirked as if to say 'That's not the road you go down – we'll see what happens.' "
This anecdote demonstrates that there was some degree of political savvy lurking beneath that handsome face. If he was gonna do it, he wanted to play his cards right.
The 2002 NY Governor election was completely FUBAR thanks to the Independence Party. That was also a big mid-term year for the GOP. Now granted if anyone has the overpowering, Goku Super Saiyan 3 aura of name recognition to overcome that, its JFK Jr. But still, its likely he either wisely sits out or indeed loses.
2006, then. Any Democrat lucky enough to have an election that year was anointed by the gods.
Can't see a path to the White House tho. Even if he wins in 2002....come on. He doesn't have that combination of effortless oratory, high emotional IQ, and subtle machiavellianism that is Barack Obama. The man is ASB. Zhirinovsky's Russian Empire was ridiculous for acting like JFK Jr could replicate that. At best he'd be a spoiler in the 08 Dem primary.
2016? NY Governor is a bad place to win "Progressive" bonafides......so unless he really crusades against Wall St corruption the NetRoots will either mildly tolerate or HATE him. Spitzer's AG background made him a natural for crusading against Wall St, but its easy to imagine Jr playing it safe and defaulting to center-left like Cuomo. Forget about tapping into Bernie's socialist well or outflanking HRC within the party.
2020? A return to Camelot after Trump pours a glass of
Rumsfeldia Lite? Okay sure. He'd be 61 on Inauguration Day though, so he'd better have more than his looks going for him by then.