Btw, my generic thinking on the Democratic nomination in 2020 is as follows:
If the Democrats have a contested primary in 2020, then it means that the GOP must have won the 2016 presidential election. The question is then, who was the Democratic nominee in 2016? The two most likely possibilities are:
1) Hillary Clinton
2) a man
(#3: A woman who is not Hillary Clinton is also possible though far less likely, as there aren't that many likely female 2016 presidential candidates aside from HRC, so it's not clear that any of them runs in '16, or that they would necessarily win the nomination.)
If Hillary Clinton runs in 2016, then I expect that a lot of the candidates who might otherwise want to run that year sit it out to avoid going up against the Clinton juggernaut. If so, then 2020 might see several of those people who we're now calling 2016 candidates (e.g., Cuomo, O'Malley, Schweitzer) finally decide to run.
OTOH, if the 2016 Democratic nominee is a man, then there'll be a strong push for him to pick a female running mate, and the two most obvious options are Gillibrand and Klobuchar. If the ticket then goes on to lose to the GOP candidate, then, assuming that losing female running mate (whether it be Gillibrand, Klobuchar, or whoever) had a decent performance on the campaign trail, she'd be in a strong position to be the early 2020 Democratic nomination frontrunner, as she'd probably be the most well known Democratic woman in the country at that point (aside from HRC, who'll be too old to run in 2020).
Sounds about right. If Hillary ran for the nomination and lost to a man (e.g. Schweizter or O'Malley), he'd probably be pressured to run with not just a woman like Klobuchar or Warren but with Clinton-loyalist Gillibrand. So she may be the 2020 favorite if Hillary ran and lost the nomination. But Hillary losing would also probably mean some other variable was going on, (like support for protectionism reaching fever pitch) and who knows how that issue's development would affect a subsequent primary?
If Hillary didn't run, and it's not for personal reasons, it might mean the GOP is headed for another wave (e.g. Romney wins 2012 and presides over a surging recovery) which might mean someone like Cuomo may wait out 2016 himself (unless he overcorrects for his father's miss) and he's a decent bet for 2020.
But in the internet age, people get presidential speculation before they even win their first guber or senate race. So the 2020 nominees may still be complete no-names right now. Still, between Hillary running for re-election, Gillibrand and Cuomo, I'd say there's a very good chance the 2020 Democratic nominee is a New Yorker.
