How far can Booker go?
Even when Booker was a Newark City Council member, people who came into contact with him said they could see him running for president someday.
"Having known him for a long time, people were talking about him being the first black president in 2001 and 2002," Gillespie said. "It is looking more plausible now."
Weingart shared a similar story.
"I think a small number of political figures who from the beginning of their career, lead people to say I can imagine him becoming president," Weingart said. "It has been true of Cory Booker."
Earlier this month, Booker ruled out the possibility of running for president in 2016. Asked by Politico whether he would rule out a presidential or vice presidential bid in the next election cycle, Booker responded with three words: "Absolutely yes, unequivocally."
But that doesn't mean never. And with the Democrats' markedly short bench on future presidential candidates, along with Booker's ability to command national attention and hefty amounts of fundraising dollars, the possibility is clearly there.
With those attributes comes another, more grandiose comparison, with President Barack Obama. Supporters, such as Gillespie, said the comparisons have to do with a mix of race, charisma and electoral history. And, of course, possible presidential aspirations.
But it is in that last regard that Gillespie looked to distance Booker from Obama.
"If Booker were to run in 2020, he would have served a full term as U.S. senator," she said, "which would be different than President Obama."
Last month, the two sides of Booker -- the political rising star and the national media figure -- came into conflict when a scheduling snafu for a speaking gig at the University of Iowa, the state that traditionally hosts the first caucus of the presidential election season, put his possible White House aspirations into focus.
All part of the game, says Weingart.
"I think Booker will have to face that," he said, referring to the mayor being asked about running for president "If he goes to Iowa, that will be looked at through the lens."
"The Democrats don't have a deep bench, so I think every conversation about the future of the party that extends past Hillary Clinton and Joe Biden, he will be on the list."