One can only imagine how agonizing it might be for former Secretary of State Hillary Clinton if the successor for her Senate seat became the first woman president instead of her.

That appears a likely ambition for New York Sen. Kirsten Gillibrand, who is trying to block President-Elect Donald Trump’s choice for defense secretary, retired Marine Gen. James “Mad Dog” Mattis — an obstructionist move that is likely to endear her to the far-left that wields outsized influence in Democratic primaries.

Gillibrand may be doing the earliest 2020 jockeying, but count on more Democrats laying the groundwork for challenging Trump in four years.

The current favorite is of course Massachusetts Sen. Elizabeth Warren, while another New Yorker and two Virginians are strong possibilities. Another run by former Maryland Gov. Martin O’Malley won’t likely make a dent, while former Massachusetts Gov. Deval Patrick will have been out of office for too long by 2020. So the focus here is on viable Democratic challengers — and how even most of those wouldn’t be that strong.

Old Guard
All will have to catch up to Warren, at least at this point. A Democratic primary poll released before the election asked who Democrats would support for the 2020 nomination if Clinton lost in 2016. Warren grabbed 16 percent of the vote; Virginia Sen. Tim Kaine, after being on Clinton’s ticket, at 10 percent; followed by New York Gov. Andrew Cuomo at 6 percent and New Jersey Sen. Cory Booker at 5 percent. “Don’t know” or “other” got a combined 62 percent percent, which might not speak well of the field.

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Warren would inspire all of the supporters of Vermont Sen. Bernie Sanders. Haters of capitalism and liberals who just want a woman to be president would likely back her. Republicans would likely favor her winning the nomination above all else because Warren has no chance of winning a general election — mostly for the reasons that make her popular on the Left.

Not only that, but Warren will be 71 by 2020. Granted, that’s the same neighborhood as Trump and Clinton’s age this year. But Democrats might see Trump’s age as a liability and want to field a youthful candidate. She’s also the mother of the overreaching Consumer Financial Protection Bureau, a federal agency that was a grab bag for the Left until a court ruling defanged the agency.

The last two losing Democratic vice presidential candidates, Joe Lieberman and John Edwards, both ran for president, in 2004 and 2008 respectively. So Kaine will likely do the same in 2020. Beyond the notoriety of a national ticket, he has the experience of being a former governor. In the Senate, he’s positioned himself well for president as a member of the Armed Services Committee, the Foreign Relations Committee, and the Budget Committee. And, at 62 in 2020, he’ll at least be younger than Warren.

But he was a rather underwhelming VP candidate, and bombed in his debate with Mike Pence. Any help to the Clinton ticket was probably minimal. Perhaps he helped her win the closer-than-expected Virginia. But with Northern Virginia overwhelmed by federal employees, and Gov. Terry McAuliffe’s felon voters, the state was almost bound to vote Democrat in this year’s presidential race.

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Then there is Cuomo, the governor of New York who may pull the political trigger his father Mario Cuomo was famously reluctant to address. The younger Cuomo, who will be 62 in 2020, is a strong orator. He also held a Cabinet position, as secretary of the Department of Housing and Urban Development. But he will lack the base’s enthusiasm that his father had in the 1980s.

Progressive Fordham law professor Zephyr Teachout mounted what turned into a surprisingly strong Democratic primary challenge against Cuomo in 2014, asserting the incumbent was too close to Wall Street. The New York Times even declined to make a primary endorsement.

While he could raise enough Establishment money to overcome the progressives’ angst in a primary, his horrendous anti-gun record — with bans on semi-automatic firearms, restrictions on ammunition, and further restrictions on sales — could prove poisonous in a general election. The number of concealed-carry licenses had skyrocketed across America in recent years.

Democrats also tend to reject dynasties. Ted Kennedy failed to win the Democratic presidential nomination in 1980, and after Clinton’s first failure in 2008, in 2016 she had a tough slog to win the nomination against Sanders, who never should have been a contender.

New Blood
New York is a big state — but not big enough to provide a base for two candidates in a primary. That’s why the aforementioned Sen. Gillibrand would likely defer to Cuomo if he runs. If he doesn’t run, she almost certainly will. Despite the early jockeying for the nomination, she might have a lot to explain to the Democratic base regarding her House career.

Before Gov. David Paterson appointed the obscure upstate House Democrat to Clinton’s old seat in 2009, Gillibrand liked to brand herself as a fiscally conservative “blue dog” with endorsements from the National Rifle Association. That said, an evaluation of her record found she wasn’t as fiscally conservative as advertised. In the Senate, she moved Left, immediately backing amnesty for illegal immigrants and taking the lead on reforming how the military deals with sexual assault allegations.

All this rebranding might make her perfectly able to pivot from a liberal in the primary to a centrist in the general. Being a woman could also be an advantage, since the Left is so focused on identity politics. But the feminist vote could split if Warren also runs. Gillibrand, however, is far more electable than Warren and given that she was no real conservative in the House, she’ll likely be able to navigate the “blue dog” issue in the primary. At 54 in 2020, she’ll also be younger than most other better known contenders.

New Jersey Sen. Cory Booker will be even younger, at 51 in 2020. The possibility of a second African-American president doesn’t bring as much excitement from the base or the media as the first. Still, Booker will be far more qualified for the presidency than Obama was in 2008, having had executive experience as mayor of Newark.

The Obama 2012 campaign took him to the woodshed after the mayor defended private equity firms from Democratic demonization. He did so because he was planning on running for higher office in very corporate New Jersey and got his chance in 2013, winning a special election after Sen. Frank Lautenberg’s death.

Another youngster would be Connecticut Sen. Chris Murphy, who would be just 47 in 2020. Similar to Republicans Ted Cruz and Rand Paul, who built presidential platforms through filibusters (or at least really long speeches), Murphy spoke for 15 hours on the Senate floor to push for gun control. Again, not an issue that will win over Middle America, but, as a House member, he represented Newtown, where the brutal 2012 Sandy Hook Elementary School shooting occurred. The empathy on that massacre would probably allow him to moderate in a national election without facing the “flip-flop” label.

The ambitious Murphy was elected to the Connecticut state Senate before he was 30, and at age 33, defeated the state’s longest-serving member of Congress, Republican Rep. Nancy Johnson, in a race many warned him against entering. After three terms, he won the 2012 U.S. Senate race. So he’s likely ambitious enough to envision himself in the White House.

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If 2016 proved anything, it’s that likability matters. Gillibrand, Booker, and Murphy might have the best edge on this front. Clinton did well among millennials who actually voted, but didn’t turn them out — all the more reason Democrats might want a younger face.

Long Shots
Others who have been mentioned don’t seem to have the heart for it.

Virginia Sen. Mark Warner likely won’t run if Kaine does. But Warner, who will be 65 in 2020, also has the benefit of having been a co-founder of Nextel Communications. Experience in business and actually creating jobs isn’t something the Left appreciates. Also, Warner barely won a second term in a tight race with Republican Ed Gillespie in 2014, which doesn’t cast him as a strong candidate.

Colorado Gov. John Hickenlooper, like Warner, has business experience as co-founder of the Wynkoop Brewing Company. The chief executive of a battleground state was a former chairman of the National Governors Association, which provided some extra national exposure. The NGA has rarely been a great boost for a presidential race. At 68 in 2020, it won’t exactly make him a vibrant challenger.

It’s also very possible someone we aren’t contemplating will run — potentially freshmen Sens. Kamala Harris of California or Tammy Duckworth of Illinois. Or someone who doesn’t hold office now. It’s still incredibly early. But, for now, with some exceptions, the Democratic bench looks quite weak.