Schweitzer on Obama: “They just haven’t been very good at running things"

[Skill and Chance]

Schweitzer's theoretical coalition here seems incredibly awkward, and a lot of the Democratic primary voters he'd probably appeal to are Clinton fans.  I just don't understand what groups he'd consolidate in theory, and certainly not when he says stuff like this.

He is trying for working class/rural Dems + people who disapprove of Obama from the left.  That is a very tough needle to thread.  But of course Obama ran the same anti-establishment strategy, but with affluent/suburban Dems + people who disapproved of (Bill) Clinton from the left and it worked out for him.  He is clearly betting that Obama will be in Bush 2008 territory by the 2016 primary.  Think of how Bryan disowned Cleveland and won the nomination in 1896.  Same idea. 

[Skill and Chance]

Schweitzer's theoretical coalition here seems incredibly awkward, and a lot of the Democratic primary voters he'd probably appeal to are Clinton fans.  I just don't understand what groups he'd consolidate in theory, and certainly not when he says stuff like this.

He is trying for working class/rural Dems + people who disapprove of Obama from the left.  That is a very tough needle to thread.  But of course Obama ran the same anti-establishment strategy, but with affluent/suburban Dems + people who disapproved of (Bill) Clinton from the left and it worked out for him.  He is clearly betting that Obama will be in Bush 2008 territory by the 2016 primary.  Think of how Bryan disowned Cleveland and won the nomination in 1896.  Same idea. 

Of course, the nomination wouldn't be very valuable if Obama was indeed in Bush 2008 levels of popularity.

That is a good point.  But it's more possible to overcome incumbent approval in an open seat election, or to lose in spite of it.  Think about 1960, 1968 and 2000.  They all should have been blowouts based on Ike/LBJ/Clinton approvals and instead they were basically tied.  Also, it wasn't close in 2008 but McCain did a lot better than Hoover or Carter.

[Skill and Chance]

Is there any example of someone running for an unpopular incumbent party and winning by running against it? I know that's how Sazkozy won but that was France.

As was already mentioned, Bryan won the 1896 nomination, although not the general. The Democratic party had lost over half their seats in the House in 1894.

There is also 1856, which was equivalent to a successful primary challenge to an incumbent president in the modern system, with the primary challenger going on to win the general election for the incumbent's party.