01/31/2009 05:12 am ET Updated May 25, 2011

Dems Consider Kennedy's Rough Road A Blessing

There are interesting, dueling dynamics emerging in the pseudo campaign of Caroline Kennedy to take over New York's soon-to-be-vacant Senate seat.

As the largely apolitical former first daughter stumbles on her early foray into big-time politics, she is, in the process, learning how to be a more formidable politician. That is the synopsis of one high-ranking Democratic official who spoke to the Huffington Post on condition of anonymity.

The individual, acknowledging that Kennedy has experienced a rough few days in her roll-out to replace Sen. Hillary Clinton, argued that the process would, in the end, be good for her long-term ambitions. Provided that Gov. David Paterson appoints her to the post, the fine-tuning would serve her well during a difficult special election in 2010 -- likely against Rep. Peter King -- and, potentially, another hard reelection campaign in 2012.

In this regard, Kennedy's attempts to win Paterson's favor represent a delicate tightrope walk: enough of a legitimate trial to forge some experience but, perhaps, too rocky a process to earn her the seat.

In private, those close to Kennedy say they anticipated the bumps and the bruises and certainly the tough press. Moreover, her allies argue that she brings to the Democratic ticket something that other, more traditionally experienced Senators could not: the ability to raise cash with little effort and forged ties to Barack Obama.

Obama, to a certain extent, actually provides a template for how Kennedy can learn on the fly. The president-elect followed a smooth road to the Illinois State Senate in 1996, when he used election rules to effectively eliminate Democratic competition. During the U.S. Senate campaign in '04, meanwhile, domestic abuse charges derailed his main primary challenger while embarrassing child custody records persuaded the Republican candidate to drop out of the race -- to be replaced by Alan Keyes.

As such, when Obama stumbled early on in the presidential primary -- lingering in the polls despite large fundraising numbers -- it was interpreted by the media as a lack of readiness for the national stage.

Of course, the similarities between Obama and Kennedy only go so far, and begin to end with consideration of each one's natural political acumen and oratorical abilities. But there are some amusing parallels to note. Kennedy, for instance, made a rocky showing of a recent New York Times interview in which she bristled at the quality of questions being asked by the reporter.

"Have you guys ever thought about writing for, like, a woman's magazine or something?" she asked David Halbfinger, before chiding him a bit further. "I thought you were the crack political team here."

Obama, too, had his early moment of conflict with the Grey Lady, as referenced in an early primary filing from columnist Maureen Dowd.

"When The Times's Jeff Zeleny asked him on his plane whether he'd had a heater in his podium during his announcement speech in subzero Springfield, Mr. Obama hesitated," Dowd wrote. "He shot Jeff a look that said, "Are you from People magazine?" before conceding that, unlike Abe Lincoln, he'd had a heater."