Occasionally, if life deals you a tremendous amount of luck, and you use it wisely, you may find yourself in a position where quite a lot of people think you’re awesome. If such a fate crosses your path, it will be exciting and stimulating and quite possibly intoxicating. This is the time to proceed with the utmost caution, as all that greatness can collapse down upon you overnight. Case in point: Caroline Kennedy.

A year ago, Caroline Kennedy was mostly known for being the last surviving child of President John F. Kennedy, and also for some charity work that no one really paid attention to. Then, on January 27, 2008, Caroline wrote an Op-Ed column for the New York Times, entitled, “A President Like My Father,” which immediately jolted her back into the public consciousness. The column (and remember, this was in the thick of the Clinton vs. Obama primaries) compared Obama’s ability to inspire to that of JFK’s:

“Over the years, I’ve been deeply moved by the people who’ve told me they wished they could feel inspired and hopeful about America the way people did when my father was president. This sense is even more profound today. That is why I am supporting a presidential candidate in the Democratic primaries, Barack Obama.”

Caroline Kennedy’s endorsement of Barack Obama is widely believed to have been the deciding factor in the decision of her formidable uncle, Senator Ted Kennedy, to endorse Obama over Clinton. Suddenly, Obama fans everywhere loved her. She was a cheering representative from one of the Democratic party’s most influential families, and she was here to help. Clinton fans were predictably angry, but they were angry about so many things that month that it was hard to keep track.

After winning the primaries, Obama appointed Kennedy to his Vice Presidential selection committee, where she helped choose Joe Biden. She attended conventions and fundraisers and smiled and reminded us of her groovy dad. Camelot’s princess could do no wrong. We all thought she was a cool person, and we all respected her opinion.

This is the exact moment when she should have fucking quit. She’d helped out; our guy had won. After Obama’s victory in November, Caroline could have nodded, said, “my work here is done,” and gone back to saving orphans or playing polo or whatever it is she was doing. Instead, she decided to see how far she could push her luck.

You probably know the rest of the story by now. Obama picked Senator Clinton to be his Secretary of State, which meant that New York Governor Paterson had to find her replacement. Giddy from Obamania, Kennedy decided that she, too, wanted to give official politics a try, and announced her interest in Clinton’s Senate seat. And the love train derailed. Kennedy conducted a television interview which, while not as moronic as any of Sarah Palin’s interviews, nevertheless brought up frightening comparisons with Alaska’s Greatest Monster. Soon arguments about sexism, privilege, entitlement, and qualification filled the airwaves, and finally, last Thursday, Kennedy withdrew her name from consideration “for personal reasons.” Probably out of sheer embarrassment. At the end of this debacle, a woman who was viewed as almost universally groovy was a beaten display of failed hubris. In other words, she failed to quit while she was awesome.

Let me try to illustrate this with a couple of sports analogies. Remember back in 1993, when Michael Jordan was the King of Basketball? He was indestructible; widely considered to be one of the best players ever. When he retired in ‘93, he could have left it at that, and spent the rest of his life doing Hanes underwear commercials. But then he decided that he wanted to play professional baseball instead. Which did not go well. He returned to the NBA in 1995, and managed to kick ass with the Chicago Bulls for three more years before retiring for a second time in 1999. Even then, Jordan could have retired with his legacy intact. But, no, he had to make another comeback in 2001, for the Washington Wizards ferchrissakes, and it all became something of an embarrassment. He retired for the final time in 2003, still beloved, but not half as perfect as he had been ten years earlier.

Or, more recently, consider Brett Favre, long-time quarterback for the Green Bay Packers. After leading Green Bay through fifteen years of excellent football, Favre announced his retirement at the end of the ‘07 season. He was all set to go down in history as a legend, both in Wisconsin and football in general. Sadly, a few months later, he decided he didn’t want to be retired after all, and joined the New York Jets, who kind of sucked this year. Favre, too, had his moment, and decided to pee all over it.

My point is, if Kennedy, Jordan, and Favre had stuck to going out on a positive note and picked up a nice quiet hobby like bird watching or playing World of Warcraft, they would have virtually flawless Wikipedia entries. Instead, their biographies drag on until they become depressing. Let this be a lesson, people.