Who can win in 2020?
It may be helpful to look at other successful candidates over the past 80 or so years.
2008: Barack Obama: A relatively fresh face, with little negative baggage, and able to inspire with both rhetoric and his relative youth, vision, and charisma. Being the man to break the racial divide didn't hurt, either. His opponent in 2008 was old, establishment, and relatively uninspiring.
2000: George Bush: Perceived as a Washington outsider, youthful, with a country type of charm that belied his silver spoon Ivy League upbringing. The loser was Al Gore, who has a wooden style and was percieved as being the ultimate Washington insider (he grew up in a Washington hotel room, after all).
1992: Another "outsider" in the person of former Arkansas governor Bill Clinton. He seemed to have it all: no DC baggage, but chief executive experience as a governor. He had an easy going good old boy charm that must have played very well to those who later would have voted for Trump. His opponent, GHW Bush, was perceived as establishment, weak, and uninspiring. Few could imagine sitting in the back yard downing a few beers with "na gonna do it"...
1988: George H. W. Bush: Exception that may prove the rule, a basically Good Man who was basically riding on Saint Ronald Reagan's coattails. His opponent, Michael Dukakis, looked puny and silly when caught donning a padded helmet several sizes too big and popping up (just barely) above the turret in an Army tank for a photo op.
1980: Ronald Reagan was the ultimate DC outsider. Plus he had loads of charisma and was a great communicator, with an instinct for what lines would move the lowest common denominators. He was facing an incumbent who appeared to be at loose ends and utterly humiliated by a two bit bunch of religious fanatics in Tehran. Carter was also supremely uninspiring to the point being downright depressing, as he appeared on TV in a sweater and urged Americans to turn down their thermostats. Reagan portrayed a much more palatable father figure, who didn't even mention denying his subjects their creature comforts.
1976: After the national "nightmare" of Watergate and the Nixon debacle, the nation was ready for a real outsider (Carter got no closer to DC than a submarine) who also was perhaps the most religious and morally upright person ever to run for the American presidency. Gerald Ford more or less sealed is own loss to Carter, when he pardoned the nearly universally reviled Richard Nixon.
1968: Although really not a DC outsider by any stretch of the imagination, Nixon somehow managed to grab that title from the very experienced and much mocked Hubert Humphrey. Nixon had spent his eight years in the wilderness, and his crafty evil genius managed to break the solid Democratic South with dog whistling and an astonishingly squeaky clean image (remember the Nixon Girls?) that took four years to be stripped away to reveal the stinking sewage of his personal plumbing outfit.
1960: This time Nixon represented the Establishment, while a youthful and extremely charismatic Jack Kennedy ran circles around him in terms of personal appeal. Which, to a nation tired of the boring Eisenhower years, acted like a tonic with amphetamines secretly added. If one looks at JFK's speeches of the day, he didn't actually propose anything substantial. Just a lot of palaver about "vigor", but the nation ate it up, and was willing to overlook questionable ballot box stuffing in the process so they could move on to the Camelot fantasy.
1952: Another establishment politician, Adlai Stevenson, failed to move voters by now weary of 20 years of liberal New Deal policies and propaganda. Had Truman decided to run again, he might have won, but he wisely decided in favor of his own domestic harmony instead. Dwight Eisenhower was able to parlay his appeal as perhaps the greatest war hero of WWII into eight years of somnolent non-rule. He had little charisma, but what he had was more than what Stevenson brought. Ike was also perceived as an outsider and a non-politician, although as head of the Allied effort in Europe he had to play politics every day.
1948: Like Bush in 1988, Truman rode on FDR's coattails and his plain speaking googly eyed look was more reassuring to voters than Dewey's hard boiled and sneaky image.
1932: FDR, another DC outsider. He'd been New York governor and also a Navy under secretary, but could afford to hang back until the time was ripe for his entrance. Oozing charisma and an uncanny ability to speak to the common man and woman from a position of wealth and social privilege, FDR seemed to be able to parlay the strength he needed in his very private battle against crippling polio into a message of strength and forbearance for the millions of Americans thrown out of work and put into desperate straits by the Great Depression. He brought hope to millions when his opposition seemed try to blame them for negative economic events beyond their individual control.
So who will the magic candidate be in 2020? It's always harder to defeat an incumbent, but chances are Trump's mismanagement will erase that advantage, as it did for Hoover, Carter, and Bush41. By 2020 Trump will no longer be able to lay claim to the outsider status, although he'll certainly try. He will eventually have to own his four years of chaos and dismay, and the time will be right for a young charismatic Democrat who will be far more credible than Trump when it comes to speaking up for the common American. Who will it be? Too soon to say, but a number of names have already been mentioned on DU. Take your pick. Just don't rely on an old warrior next time.
= new reply since forum marked as read
Bernie & Elizabeth 2020!!!
I wasn't referring to Hillary. In none of these comparisons was I talking about the primary battles, just the general election.
And in 2008, Obama's opponent was John McCain, who WAS old and uninspiring.
And I purposely left out the 2016 general election, because then this thread would have belonged elsewhere 
After all, Trump was born and raised in NYC, which is still his main residence.
Clinton, born and raised in the Mid-west.
Obama, Hawaii - can't get much more West Coast than that
More important will be personality, charisma, and lack of baggage.
