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The 28 hours Joe Biden spent in New York City at the end of last week were a whirlwind of activity—much of it feeding the mounting speculation that he is inching ever closer to launching a late-starting presidential campaign. Biden stood alongside Attorney General Loretta Lynch and announced an $80 million plan to clear the backlog of rape kits in police departments around the country. He appeared with Governor Andrew Cuomo at a rally with some of the city's most powerful unions to support Cuomo's push to hike the minimum wage. He made his now-famous appearance on the Late Show with Stephen Colbert. He took part in an evening roundtable for the Democratic Senatorial Campaign Committee. And, the next day, he delivered remarks at a 9/11 memorial aboard the Intrepid Museum, at which firefighters, cops, and other first responders chanted, “Run, Joe, run!”

Each of these events was freighted with political meaning. For some, the turn on Colbert, with Biden expressing his enduring anguish about the loss of his son Beau and his heartfelt doubts about his ability to rise emotionally to the rigors of a campaign, was the most telling, signaling what many in the political establishment have believed for weeks: that for all of Biden's dalliances with a bid, he would in the end find himself unable to get to yes.

And that may still prove true. But fewer than 12 hours after the Colbert interview aired, Biden partook in a meeting that signaled something entirely different. The meeting appeared nowhere on his public schedule. It was held in secret at his hotel in Midtown Manhattan and lasted for more than 90 minutes: a private, one-on-one session with one of the most prominent and powerful fundraising stars in the Democratic firmament—a mega-bundler who happens to be, at least for now, publicly committed to Hillary Clinton.

Robert Wolf sits for a photograph in his office in New York on April 20, 2015. Photographer: Chris Goodney/Bloomberg

The bundler in question was Robert Wolf: the former chairman and CEO of UBS Americas, a prodigious buck-raker on behalf of Barack Obama in two successive campaigns, a four-time appointee to economic panels in the Obama administration, and perhaps the only person in the American business community—and certainly the sole Wall Street potentate—with whom Obama during his time in office has developed a deep and genuine friendship. (The two are frequent golf partners, most recently last month on Martha's Vineyard, where they were part of a foursome with Larry David and White House senior adviser Valerie Jarrett's cousin Cyrus Walker.)

Having picked up scuttlebutt about a possible Biden-Wolf tete-a-tete on Friday, I phoned Wolf over the weekend to see if it was true. Wolf, whom I've known since he first backed Obama in early 2007, confirmed that the meeting had taken place. The topics they discussed, Wolf said, ranged from the reauthorization of the Export-Import Bank to the nation's crumbling infrastructure, a focus of Wolf's consulting firm, 32 Advisors. When I asked him if Biden had declared definitively that he was running, Wolf said no. Had Biden made a plea for Wolf's support? Wolf again said no—and pointed out he was supporting Clinton. Had Wolf come away with the impression that Biden was going to run? “If he doesn't know yet,” Wolf said coyly, “how would I?”

Wolf is by nature a straight shooter. But both the timing of the meeting and its furtiveness strongly suggest there is more here than meets the eye. Though Biden and Wolf have crossed paths at the White House over the past seven years, Wolf admitted that until last Friday, they had never had a sustained or personal conversation. Now, suddenly, he found himself swapping stories with the vice president about the closeness to their sons (like Biden, Wolf is a father of two). Just as it would take a stratospheric degree of political naivete to believe that, at this moment, Biden summoned Wolf to his hotel to discuss infrastructure—unless the infrastructure in question was that of the nascent Biden 2016 effort—it would require a willful blindness not to see the get-together for what it plainly was: the beginning of a courtship, and potentially one of considerable political consequence.

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If Biden does decide to run, the benefits of landing Wolf would be many, some obvious and some subtle—but all perfectly clear to each party. First, having raised north of $500,000 for Obama in both 2008 and 2012, he could be a source of a great deal of campaign cash. Second, he could help Biden establish ties to Wall Street, where the V.P. has few. Third, he could be a valuable adviser on economic matters, where the priorities of the two are in sync. Fourth, Wolf's defection from the Clinton camp would be a major symbolic blow to her already reeling campaign. And fifth, given Wolf's closeness to Obama, the move would carry with it the widespread (and likely accurate) assumption that the president had blessed it.

Heilemann: Wolf’s Backing Would Be a 'Huge Get' for Biden

How susceptible Wolf might be to any future Biden entreaties is an open question. In 2008, Wolf sided with Obama over Clinton when the vast majority of his Wall Street compatriots did the opposite. And while he is publicly committed to Clinton and has written a check to her for $2,700, the individual maximum contribution, he has not signed on as a “Hillblazer” bundler or raised a dime for her so far. Eight years ago, a large part of Wolf's decision to throw in with the challenger arose from his sense that he would never have a seat at the A table with Clinton—that with all of the concentric and cacophonous circles of hangers-on around her, his voice would not be heard. Eight years later, those circles are even wider, more crowded, and more deafening.

Biden's outreach to Wolf is notable on many levels, but one in particular stands out. The vice president has been quietly meeting and talking by phone with donors around the country as he has ramped up his exploration of a bid. But this is, I believe, the first known instance of him sitting with a top-drawer bundler officially in the Clinton camp. Biden thus far has moved cautiously with respect to riling the former first couple. He now apparently has adopted a somewhat more audacious posture.

WATCH: Is Joe Biden More Likely to Run After ‘Late Show' Appearance?

On another level, the Biden-Wolf meeting is just one more sign of the rapid acceleration of planning and preparations going on all throughout Bidenworld—the scramble to create a campaign-in-waiting. On the fundraising front, the V.P.'s people took particular notice of a recent piece in the Washington Post, which reported that the vast majority of those who raised big dollars for Obama in 2012 are still effectively up for grabs. Calls from Biden's realm to those unsigned bundlers are being made at a furious clip—even as calls are flooding in unbidden in the opposite direction.

For Biden's people and the vice president himself, the response to his increasingly ardent flirtations with a run—not just among donors but elected officials, strategists, the press, and ordinary voters—have been encouraging in the extreme. In light of the trajectory of the polling numbers nationally and in the early states—bad and worsening daily for Clinton, respectable and improving for Biden—the V.P. and his team have come to believe that there is scant doubt an electoral opening exists for a Biden candidacy. And their collective sense of confidence that, in purely practical terms, an effective national campaign apparatus can be built is nearly total.

Skeptics, of course, insist that, by putting off his decision until late this month or early next (the timetable his people have floated), Biden has already waited too long to make his entry. Among the V.P.'s adjutants, though, a different view prevails: not only is it not too late, but it may make sense to wait even longer. Indeed, according to multiple sources familiar with the planning under way, Bidenworld is now gaming out, and perhaps even leaning towards, a new timetable—with the vice president waiting until late October or early November to join the race.

This new scenario would have several distinct disadvantages. It would mean skipping the first Democratic debate on Oct. 13 in Nevada. It would mean missing the annual Jefferson Jackson dinner in Iowa on Oct. 24, an event traditionally of no small political importance. It could mean missing the Florida Democratic Party convention on Oct. 31 and Nov. 1.

But the new timetable might offer certain upsides. It would afford Biden and his people the chance to gauge whether Clinton is able to reverse her slide—or, on the contrary, reap the benefits from an enhanced sense of Democratic unease if her skid continues. It would, in particular, let Biden wait until after Clinton's Oct. 22 testimony to the House Select Committee on Benghazi, which might conceivably exacerbate her current maladies. It would still allow Biden to meet the handful of primary/caucus filing deadlines that commence in early November. It would give Bidenworld more time to put the functional pieces of a campaign in place. And it would give Biden himself more time to come to terms with the emotional turmoil still roiling inside him—and to be certain his family is in favor of him running, as well as being genuinely prepared for what it would entail.

No one close to or currently advising Biden doubts that the weight of those psychic burdens may yet keep him from running. Some of his longest-standing and most loyal adjutants remember Biden's deliberations in 2004, when it seemed every day he was ever closer to getting into the race—until the day he woke up and said he wouldn't. They see him pushing back the decision date and take that as a sign that the fire really, truly isn't in his belly. They remain convinced that, although they admit he is much more gung-ho about diving in now than he was a month ago, his sense of duty to his family will overrule his political ambitions and gathering sense of opportunity.

“You have to understand,” one person in his innermost circle for decades told me, “the vice president sees himself as the patriarch of his family in the most traditional, old-fashioned sense. This won't be a family vote. Jill, Valerie, Hunter [his wife, sister, and surviving son], and the others may not say no, may say they want him to run. But he's really worried about them—what this would mean for them, whether they're really ready. He sees it as his duty not just to ask them their opinion. He sees it as his duty to take care of them. And here's the thing that makes it all the harder: There used to be a deputy patriarch in Beau, and now he's gone.”

But what those close to Biden and others who have spoken to him in recent days also say is this: that he believes, after two miserably failed bids for the White House, 2016 may finally be his time; that he is convinced he is suited, perhaps uniquely, to a moment when authenticity is more prized than ever in our politics, so prized that someone as unlikely as Donald Trump could have become the overwhelming Republican front-runner based to a large extent on the perception that he “tells it like it is”; that he not only sees the Clinton campaign as performing poorly, but believes he possesses something that the fading front-runner does not—a clear and coherent understanding of why he wants to be president, and the ability to express it in a way that voters would find ... real.

These are the sentiments that Biden is expressing to the people all around him. In the end, to be sure, none of it may matter. “Fundamentally,” says the longtime confidant, “this will be decided by a conversation between Joe Biden and Joe Biden.”

But increasingly, gradually, a little more each day, it appears that the Biden who wants to run is the one doing most of the talking.

Kendall Breitman contributed reporting.

( Adds detail on factors influencing Biden's timetable in 14th paragraph )