Speaking at the same dinner three years ago, he was grappling with a decision to make a late entrance in the 2016 presidential race mere months after the passing of his son Beau.
The circumstances are different this time around (it's earlier in the process), but he is still mulling whether a third run for the White House could be the charm as he starts a campaign blitz for Democrats ahead of the midterm elections.
Biden, who ran failed bids in 1988 and 2008, has publicly said he'll decide about 2020 by January, a time frame that sources close to the former vice president say mirrors his private discussions. But as he travels across the country, including to key presidential battleground states, his longtime network of loyal donors and operatives are watching and waiting for signs that he is inching toward a presidential run.
"He certainly feels the push from people who want him to run, so of course it's there," one Biden adviser said. "But in terms of the nuts and bolts of planning his time and thinking of what he's doing, he's focused on how he can be of most help to the Democratic Party."
Biden took direct aim at President Donald Trump on Saturday night, noting that "forces of intolerance remain determined to undermine and roll back the progress you have made."
"Instead of using the full might of the executive branch to secure justice, dignity, and safety for all, the President uses the White House as a literal, literal bully pulpit, callously exerting his power over those who have little or none," he said.
Crisscrossing the country
He kicked off his midterm campaign sprint by literally running through a Labor Day parade in Pittsburgh alongside union workers -- a group at the heart of his blue-collar, middle-class message.
"I've been with these guys my whole life," Biden said. "These are the guys that brung me to the dance, as the saying goes."
In the first week of October, Biden will make a three-day swing to California and Nevada to raise money and hold public events, including a likely stop with Democratic Senate candidate Jacky Rosen in Nevada, a source with knowledge of the plans tells CNN. Democrats see a real pickup opportunity in Rosen's race against incumbent GOP Sen. Dean Heller.
It's all part of Biden's push to be one of the most active Democratic surrogates on the trail this fall with the pace of his campaigning picking up in October. His team says he's squarely focused on getting Democrats elected in 2018 --- but nearly everywhere he goes questions about 2020 loom.
A third run for President?
Headlining the dinner for the country's largest lesbian, gay, bisexual, transgender and queer civil rights group on Saturday gave Biden, the first vice president to back same-sex marriage, a chance to stay connected to a key portion of the Democratic base. As the former vice president started his speech, a few people in the crowd yelled "Run Joe!" He responded, "Thank you."
Biden has said that after the midterms he'll engage in an "altar call" to gauge whether the support exists for a run, and the final verdict about whether he'll launch a bid will boil down to a family decision.
Biden's brain trust includes longtime strategist Mike Donilon; former chief of staff and the managing director of the Penn Biden Center Steve Ricchetti; former Sen. Ted Kaufman of Delaware; executive director of the American Possibilities PAC Greg Schultz; and former communications director Kate Bedingfield. His sister, Valerie Biden Owens, who managed each of his campaigns, remains a trusted confidante.
Should he decide to launch a 2020 bid, Biden could tap into a network of supporters, donors and aides that spans decades.
"As far as any candidate that I think has shown an interest, Joe would be by and far the one person that I would get out and support wholeheartedly," said Bruce Hunter, an Iowa state representative who's a longtime supporter of Biden's.
"We are asking and he's saying, 'I'm not even going to contemplate that till after the midterms,' " said George Tsunis, an Obama bundler who wanted Biden to run in 2016. "I would be very excited for the country if he were to do that. I think he's very, very capable."
Midterm plans taking shape
For most of the last year, Biden's campaign work primarily focused on doling out endorsements and raising money for Democratic candidates, particularly incumbent senators in states that Trump won in 2016. Later this month, he'll appear at a fundraiser for the Democratic National Committee in Boston.
But his attention in these final weeks before the election will shift to classic Joe Biden retail politicking as his team crafts a robust but flexible schedule to appear with candidates.
"I'm updating my travel in real-time to make sure I'm as effective a voice as I can possibly be for the incredible set of diverse, strong leaders we've endorsed," Biden wrote in a fundraising email from his political action committee American Possibilities.
To date, Biden has publicly endorsed more than 75 Democratic candidates for Senate, House, governor and other state-level races. Those earning endorsements range from Obama administration alumni -- like Andy Kim in New Jersey's 3rd Congressional District; Gina Ortiz Jones in Texas' 23rd Congressional District; and Elissa Slotkin in Michigan's 8th Congressional District -- to longtime friends like New York Gov. Andrew Cuomo, whom Biden praised in a TV ad that blanketed the New York media market ahead of this week's primary.
Biden's advisers say they are mapping out plans for the former vice president to hit industrial states in the Midwest as well as Florida to help in Senate and governors' races. He'll also be a frequent fixture in Pennsylvania and New Jersey -- where a handful of close races could help Democrats win control of the House.
"I think that Vice President Biden resonates deeply throughout the country," said Valerie Jarrett, who was a top adviser to former President Barack Obama. She added that the Democratic Party is "fortunate to have someone as compelling and popular as Vice President Joe Biden traveling as actively as he is in the midterms."
But there are two high-profile states Biden won't set foot in before Nov. 6 -- Iowa, where he endorsed state Rep. Abby Finkenauer in the state's 1st Congressional District, and New Hampshire. His team says any visits to the early presidential caucus and primary states run the risk of shifting attention from the candidates to his presidential ambitions.
A visit to South Carolina, the third nominating contest, is under consideration, but his team argues that's different due to Biden's long-term connections to the state -- where he has endorsed Democratic gubernatorial nominee James Smith, who is a close friend of the Biden family, including the late Beau Biden.
"Joe Biden's been coming to South Carolina since the 1980s," said Dick Harpootlian, a longtime Biden supporter who earned the former vice president's endorsement in his state Senate race this year. "He's participated in Democratic primary politics here. When he was vice president, he helped us raise money. He's almost a local."
A stop in Georgia, where he endorsed Stacey Abrams, a progressive African-American candidate for governor, is also a potential option.
Aside from the avoiding-Iowa-and-New-Hampshire strategy, Biden's team is adamant that 2020 will not play a factor as they plan out his trips.
But he is notably eyeing visits to help candidates in Florida, Ohio, Michigan, Pennsylvania and Wisconsin -- all competitive races but also five of the six states Trump flipped from blue to red in 2016 that Democrats are eager to win back.
Navigating Obama and the Democratic field
The one Democratic surrogate who could eclipse Biden for attention during the midterms is Obama, who stepped into the political fray last week as he criticized Trump by name for the first time.
Biden and Obama have maintained a close relationship since leaving office. They speak from time to time, but the contact is not as frequent as their daily check-ins and weekly lunches at the White House, of which Biden so often boasted. In July, they got the gang back together for lunch at a Georgetown bakery that helps veterans and military families.
When Biden debuted his Instagram account, which quickly racked up over a million followers, the former president welcomed him by posting a selfie of the two, writing, "you'll always be one of the rare exceptions to my no-selfies rule."
Obama has made few appearances with other candidates mulling 2020 bids. But he has held meetings with several Democrats considering runs to dole out advice about running in the Trump era and how to best set up the party for the future.
He has typically refrained from endorsing in primary races, so it's unclear if he will wade into the presidential primaries in 2020 to endorse his close friend Biden or any other candidates he's impressed by. One Democrat close to the former president said there have been no discussions of endorsements at this point.
Before any potential Biden-Trump campaign face-off, Biden would need to tackle a crowded Democratic primary field -- where dozens of names have been floated as possible contenders.
The former vice president could find himself competing against progressives like Sens. Bernie Sanders of Vermont and Elizabeth Warren of Massachusetts at a time when much of the energy in the Democratic Party comes from the left.
Biden, who would be 77 as the nominating contests get underway, may also be stacked up against a crop of younger, fresh-faced Democrats such as Sens. Cory Booker of New Jersey and Kamala Harris of California. The current President is three years younger than Biden.
"I think Vice President Biden is one of those candidates who actually can go to any place in America and be well received, whereas others may be less well received," said Robert Wolf, a Democratic donor and friend of Obama and Biden. "He sits in a great seat -- but getting through a Democratic primary I have a feeling will not be easy for anyone."
Trump vs. Biden
"A dream."
That's how Trump recently described a potential run against Biden in 2020.
"President Obama took him out of the garbage heap, and everybody was shocked that he did. I'd love to have it be Biden," Trump said in an interview with CBS News.
Biden recently launched a sarcastic jab of his own at Trump.
"I'm clearly not as smart as Trump, the smartest man in the world," he said to laughter at a DC speech. "But I have a relatively high IQ."
The verbal brawl between the two initially escalated earlier this year, when they started talking about physically fighting each other.
"A guy who ended up becoming our national leader said, 'I can grab a woman anywhere and she likes it,' " Biden said in March referring to Trump's "Access Hollywood" tape. "They asked me if I'd like to debate this gentleman, and I said no. I said, 'If we were in high school, I'd take him behind the gym and beat the hell out of him.' " Biden's comments were similar to ones he had made in 2016.
Trump bit back on Twitter, writing, "Crazy Joe Biden is trying to act like a tough guy. Actually, he is weak, both mentally and physically, and yet he threatens me, for the second time, with physical assault. He doesn't know me, but he would go down fast and hard, crying all the way. Don't threaten people Joe!"
Biden later expressed regret for his comments.
"I shouldn't have said what I said. I shouldn't have brought it up again because I don't want to get down in the mosh pit with this guy," he told "Pod Save America." "The idea that I would actually physically get in a contest with a President of the United States or anybody else now is not what I said, and it is not what this was about, but I should have just left it alone."
According to an Axios report, advisers to the President have said Biden is the Democrat he fears running against the most. A CNN poll of registered voters conducted in January found Biden leading Trump 57% to 40% in a hypothetical match-up.
One Biden adviser said they expect his criticism of the President this fall to be more implicit than explicit. Biden has already previewed some of that messaging as he's talked about respect, dignity and American values, and he's frequently lambasted the "phony populism" and "naked nationalism" he thinks the President and the Republican Party promote.
"I think he will speak about his values and his core values of the Democratic Party that represents the best interest of all Americans," Jarrett said. "I think he will also contrast to what's happening today, similar to what President Obama -- the policies and the rhetoric that we're hearing today is inconsistent with those values."
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