Betting against Bernie? Dems assess the risk

Bernie SandersBernie SandersThe Memo: Trump faces steep climb to reelection California Democrats face crisis of credibility after lawsuits Fox's Brit Hume fires back at Trump's criticism of the channel MORE’s second run for the White House looks like it will be harder than his first. But in some ways, it may also be easier.

Vermont’s independent senator will have to share the progressive lane in 2020 with other top-tier Democratic candidates, including Sen. Elizabeth WarrenElizabeth Ann WarrenThe Memo: Trump faces steep climb to reelection Feehery: A whole new season of 'Game of Thrones' Overnight Energy: Warren wants Dems to hold climate-focused debate | Klobuchar joins candidates rejecting fossil fuel money | 2020 contender Bennet offers climate plan MORE (D-Mass.), who doesn’t have to take a back seat to Sanders when it comes to being a progressive.

Instead of being the liberal challenger to Hillary ClintonHillary Diane Rodham ClintonThe Memo: Trump faces steep climb to reelection What the Mueller report tells us about Putin, Russia and Trump's election Steve Bullock puts Citizens United decision at center of presidential push MORE, Sanders, 77, faces a crowded field where he’s the returning candidate battling fresher faces such as Sens. Kamala HarrisKamala Devi HarrisThe Memo: Trump faces steep climb to reelection California Democrats face crisis of credibility after lawsuits Feehery: A whole new season of 'Game of Thrones' MORE (D-Calif.) and Cory BookerCory Anthony BookerDe Blasio pitches himself as tough New Yorker who can take on 'Don the con' Sanders pledges to only nominate Supreme Court justices that support Roe v. Wade From dive bars to steakhouses: How Iowa caucus staffers blow off steam MORE (D-N.J.).

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He also must deal with the fallout from 2016, including grudges from Clinton supporters who feel Sanders cost her the election and Democrats who don’t want to turn their party over to an independent.

At the same time, it would be hard to argue that the Sanders path to a Democratic presidential nomination is more unlikely in the 2020 cycle than it was four years ago.

Sanders is no longer an unknown candidate. He’s a household name and is getting the attention and money that come with political success. His campaign said it raised $3.3 million Tuesday, the day of his announcement. In comparison, Harris raised $1.5 million during her first 24 hours, while Sen. Amy KlobucharAmy Jean KlobucharFox's Brit Hume fires back at Trump's criticism of the channel Overnight Energy: Warren wants Dems to hold climate-focused debate | Klobuchar joins candidates rejecting fossil fuel money | 2020 contender Bennet offers climate plan O'Rourke says he would 'absolutely' do Fox News town hall MORE (D-Minn.) raised $1 million in 48 hours.

Once an upstart challenger and an unknown, Sanders now enjoys a loyal grass-roots organization in every state in the country — a point allies were happy to highlight on Tuesday.

And it’s possible the large Democratic field will leave Sanders standing alone at the end, if Democrats are divided among a number of candidates and a core group sticks with him.

“It’ll be so much easier,” said one Sanders source close to the campaign, who added that even if Sanders loses 10 percent of his 2016 supporters to other candidates, he’ll still be ahead of the 2020 pack.

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Others aren’t so sure and think that Sanders might have missed his political moment when he failed to defeat Clinton in 2016. Those doubters include President TrumpDonald John TrumpThe Hill's Morning Report - White House, Congress: Urgency of now around budget GOP presses Trump to make a deal on spending Democrats wary of handing Trump a win on infrastructure MORE, who said Tuesday that he thought Sanders’s time had come and gone.

“It’ll be harder for him without a doubt,” said Bill Press, the talk-show host who served as a surrogate for Sanders during his 2016 bid. “He’ll have to work harder to hold on to the supporters he had the first time around.” 

Even before he announced his candidacy on Tuesday, Sanders had already lost a key surrogate in Rep. Barbara LeeBarbara Jean LeeOvernight Health Care: HHS issues rule requiring drug prices in TV ads | Grassley, Wyden working on plan to cap drug costs in Medicare | Warren to donate money from family behind opioid giant Dem lawmaker shares video of herself dancing to Beyonce for Dance Week Lawmakers renew push to create American Latino Smithsonian museum MORE (D-Calif.), who announced her support for her home-state senator Harris. 

Sanders allies say their candidate has a solid path to the nomination. They say he must win over independent voters who identify with his politics as well as white working-class voters in Rust Belt states and traditionally red states such as Kansas, where Sanders performed well in the 2016 primary. 

Regardless of whether Sanders wins the 2020 nomination, his supporters will argue he’s leaving a mark on the party.

The single-payer health care plan he championed is now backed by a number of Democrats, including Warren, Harris and Booker. He backed Rep. Alexandria Ocasio Cortez (N.Y.) in her primary fight, and she has become one of the biggest Democratic stars.

And his fundraising prowess suggests it would not be wise to underestimate him.

The senator is also among the front-runners according to polls. An Emerson College poll shows him in second behind former Vice President Joe BidenJoe BidenThe Hill's Morning Report - White House, Congress: Urgency of now around budget The Memo: Trump faces steep climb to reelection Trump: Foreign countries want Biden in office so they can continue 'ripping off' the US MORE, who has yet to say whether he’ll enter the race.

To win, those aligned with the Sanders campaign say he’ll have to make inroads with older white Democrats, who have traditionally been more in line with the establishment. Older women in 2016, for example, leaned Clinton. 

Clinton supporters are still miffed at Sanders for being a “reluctant surrogate” — as one Clintonite put it — during the general election. They say he has done little to mend fences.

“He’s done a good job appealing to the Bernie base. But with a two-year head start on everyone else has he even tried to appeal to the 17 million Democrats who voted against him?” said Philippe Reines, a longtime adviser to Clinton. “It doesn’t seem like he cares too, which is exactly Donald Trump’s approach to winning people over.”

Democratic strategist Jim Manley — who served as a Clinton surrogate in 2016 — said that while Sanders played a big role in pulling the Democratic Party’s policy debate to the left in the past two years, he said he wonders if Sanders still has the gravitas to pull in voters a second time around. 

“The question is if voters are looking for a fresher face,” Manley said. “There is a lot of energy on the left, but he’s going to have to work hard this time to differentiate himself from the others. There are no slam dunks in life and certainly not in this election year.”