The challenges Weiner faces are numerous. The Democratic primary is crowded. Other candidates have been building their campaigns for months now. Indeed, many of Weiner's former staffers are already working with the other candidates. Though he has enough funding to be instantly competitive, Weiner would need to quickly build a campaign organization from the ground up. And, of course, there's the scandalous baggage he now carries.
George Arzt, a political consultant with over four decades of City Hall experience who isn't working with any of the candidates in this year's race, said it would take a major shift in opinion for Weiner to win.
"Unless people are just sick of the field, that is the only way that he could be a viable candidate," said Arzt. "If he gets ten to fifteen percent, I would call that a victory."
New York is a staunchly blue town and polls are showing the Democratic candidates well ahead of potential GOP opposition. With City Council Speaker Christine Quinn holding a strong lead, the other three major Democrats have been trying to tack to her left. This makes it an especially competitive field for a progressive firebrand like Weiner. Multiple operatives we spoke with questioned whether he has any opening to take a plurality of voters from the other candidates.
Stuart Osnow, a founding partner at the political consultancy Prime New York, which isn't representing any of the mayoral candidates, said he doesn't see how Weiner has any characteristics that aren't represented by other Democrats who are already in the running.
"He's got money, so that makes him a player," Osnow said before adding, "It's not clear what new things he brings to the race."
"He had two bases," one Democratic operative already working on the race said of Weiner. "He had this outerborough, Jewish, white base and I think those people are going to be much less forgiving of his transgressions. He also had this kind of white Manhattan base and I think, to the extent that he can get those people back, he's going to be taking mainly from Christine Quinn's pile, but I just can't see how that's ever going to be enough to get him into a runoff."
That operative said Weiner has no "history of having a base" in the rest of the minority community and would have trouble drawing more liberal city residents since there are other candidates aiming at that part of the spectrum who aren't carrying as much scandal baggage.
"Why would you vote for Weiner when there's a perfectly acceptable, progressive alternative? I just don't see it." the operative said.
It goes deeper than doubting Weiner can win. Several of the Democrats we talked to don't even seem to think he can make a meaningful impact on the race and affect the other candidates' relative positions in any notable way. Though there has been speculation about a potential Weiner mayoral bid for months now, we heard from staffers on multiple Democratic mayoral campaigns who said they have not bothered to include him in their internal polling.
For his part, Arzt speculated Weiner, whose congressional seat was in Queens, could have a strong impact on one hopeful, Bill de Blasio, who also represented areas outside of Manhattan. Arzt also guessed Weiner could benefit the two minority candidates, Bill Thompson and John Liu.
"He probably would damage de Blasio tremendously, because he's an outerborough person. He probably would hurt Quinn a little, take some away, but not enough to be consequential," Arzt said of Weiner. "Liu it helps, Thompson it helps I think, overall, having another white guy in the race."
In spite of these predictions, Arzt doesn't think Weiner's presence in the race will be game-changing.
"I always thought that it would be Thompson and Quinn in a runoff and I still do," said Arzt.
Osnow agreed Weiner won't have an affect on the outcome and said, if anything, his presence could boost Quinn, who already has a wide lead in the polls.
"Maybe he enhances Quinn's chances because he adds another man [to the field]," Osnow said.
Osnow also predicted women will still hold Weiner's past against him and suggested that might galvanize more support for Quinn.
One operative working with a Democratic mayoral candidate said Weiner could be a "viable candidate," but they doubted his ability to make up for lost time against opposition who have been "rolling" and "building infrastructure."
"It's hard enough to campaign in a big city as it is," the operative said. "When the first thing you're doing is apologizing for your behavior and asking for a second chance, that's not tremendous place to start."
Some Democrats we spoke with also took issue with the tone of Weiner's Times Magazine interview, which focused on his family's experience of the scandal and his desire to return to public life.
"You know what he should do? He should do something substantive. This calculating article and then the calculating this, and the calculating that, and the crying, and the narcissistic comments. He should just like start a foundation. He should do something good for somebody other than himself," one Democratic city elected official said. "That article was all about him taking, what about me? Will they accept me? Will I get to be on the red carpet again? Do I get to go to the correspondents dinner? Woe is me!"
One of the Republican candidates wasn't at all worried about facing Weiner in the general election this November. "I don't think he'll make it that long," said the candidate. He would become the quest of all the late night show jokes. I think he'll rekindle all the comedians at night."
In spite of all of Weiner's doubters, one person we spoke with said they see a potential path to victory for him. A well-placed political insider who knows Weiner said they wouldn't be shocked if the people preoccupied with Weiner's slim chances in the Democratic primary were missing his real route to City Hall -- a bid on a third party line.
"Anthony is going to look at this from a completely insurgency point of view," the insider said. "Anthony is the king of triangulation."
The insider suggested Weiner could be talking with New York's infamous Independence Party and that, on any party line, he could do well in a general election against Quinn and a Republican.
"I think he's doing this truly from the point of view of guerilla warfare insurgency," the insider said.
Arzt thinks Weiner has "no chance on a third party" either, but he said there still may be a way this race could end in a win for Weiner.
"He obviously has an uphill fight, but I don't think he's in it -- if he goes into the race, he won't be in it to win as much as to cleanse his name and to get on with his life," said Arzt. "Even if he loses, he can go on and be a talking head on TV or radio, so he needs to get this act out of the way."
Weiner declined to be interviewed for this story, so it's impossible to be certain about his thinking. But he suggested in his interview with the Times Magazine that he sees the window for his electoral career possibly closing.
"I don't have this burning, overriding desire to go out and run for office," said Weiner. "It's not the single animating force in my life as it was for quite some time. But I do recognize, to some degree, it's now or maybe never for me, in terms of running for something."
Weiner's former congressional district, where he enjoyed strong support even after the scandal, was eliminated in the most recent round of redistricting. New York currently has relatively high-profile, established politicians occupying its seats in the Senate and the governor's mansion. All of the Big Apple's main citywide offices; mayor, public advocate, and comptroller, are open this year meaning waiting until the next election cycle will guarantee Weiner faces a fight against an entrenched municipal incumbent. Even if he would be willing to forgo the mayor's race for a shot at one of the lower two positions, 2013 will likely be Weiner's clearest shot at winning an office with upward mobility in the next eight years.
He may be a longshot to win this election, but with a tarnished reputation and few other prospects for a political future, he can't really lose either.