The 2008 Oregon senate race was a disaster , Gordon Smith deserved reelection , and now we can have president Merkley (that will suck ).
In my personal opinion it was Gordon Smith's support for the Iraq War that caused his loss in '08, and Merkley's strong opposition to the Iraq War that put him over the finish line, in what was an extremely close election.
Voters had long since forgiven Gordon Smith for his previous support for the anti LGBT Oregon Citizen's Alliance (OCA), and the economy in Oregon hadn't fully collapsed by 11/08, since there is always a lag historically during Recessions because of the Timber industry, as well as other manufacturing related activities in the State.
That said, Merkley has some pretty solid foreign policy chops going into 2020 because of that opposition to the War, which not only fits the current mood of the Democratic Base, but arguably the American electorate at large, where even Donald Trump tried to run as an "Anti-War" candidate during the Republican primaries.
Merkley's progressive economic policies generally fit within much of the American mainstream, where support for increasing the minimum wage dramatically is fairly popular, even in Republican states like Missouri, and the whole Main Street vs Wall Street style of economic populism tends to play well.
We can quibble about items like expanding government funding for college tuition, and how exactly to fix the current Health Care system, but by and large a decent majority of Americans actually support the fundamental goals, but disagree on the exact solutions required.
On Culture War items, Merkley is definitely solidly in the Progressive Camp, but is a bit more subtle in his approach than several of the recent Democratic Party Pres nominees, and isn't someone that can be easily accused of "demonizing" the Religious Right elements, or solely "representing SF/NYC/MA Liberal Coastal Elite Values" (Standard Republican playbook)