Aside from Hillary I don't know much about these people, and I don't think the American populace as a whole does either. Sanders might give Hillary some competition aside from that it seems like the rest won't matter much.
Sanders has a bit of a hipster appeal and is popular among the more hard left base of the party, but he probably wouldn't do well in a general election.
Hillary has the name recognition.
Maybe Chafee will try to say that he is better than Hillary since he openly supported "Marriage equality" before it became the party line, so he can be a bit avant garde and "forward thinking" but he was governor of Rhode Island which is fairly small, so if he goes against a Florida or Texas governor it will look bad for him.
Webb is Virginian so he's a Southerner, so maybe he can try to say he understands both North and South. O'Malley, I don't know what I can say he has going for him
Anyways my picks:
1. Most likely to win Nomination: Hillary. Sanders in 2nd place.
2. Who I most want to win strategically: Chafee or O'Malley, they seem the easiest to beat.
3. Who I probably like the best: maybe Webb? He's probably the most centrist.
Dems will have a hard time in 2016 for a variety of reasons (though Repubs have to be careful not to be seen as either soft on immigration or overly hostile to immigrants)
1. The trend - usually one party does not win three pres. races in a row.
2. 2012 - it was closer than it looks. If Reps hold the states they won then, they only need to pick up OH, FL, VA, and one more state (and CO, NH, NV, and Iowa are all vulnerable)
3. Black turnout will probably be lower with Obama not running.
4. National Security - Republicans have regained their traditional polling advantage on this category, Dems led in that category in 2008 and 2012.
5. Democrats might move too far to the left
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