2008: Gordon Smith and Norm Coleman win

[Escape Pod Zero]

These two blue state GOP senators just barely lost in 2008. If they had won, how would they have done in 2014 and today?

Even though 2014 was a red wave year, I could see polarization bringing them down. If they survived that, then they would surely be massive underdogs in 2020.

[President Punxsutawney Phil]

No Republican Senator was going to lose in 2014. Gordon Smith was a strong incumbent anyway, he only barely lost in face of a massive tidal wave. Norm Coleman was also decently strong but if he had won in 2008 he should have survived 2014 by a margin of, I guess, low single digits.
The real crunch time would be 2020, where they would, like Mark Kirk in 2016, be facing the end of the line.

[Left Wing]

I think Norm wins in 2014 for sure. Smith would have a tough time, but if he was able to pull through in 2008, I think he could do it in 2014. Obamacare would basically have to be completely gutted to get past the 60 votes needed. This might have caused a less strong R wave in 2010 but GOP fearmongering about the bill would have occurred anyway. Smith and Coleman could have been 2012 or 2016 candidates, but I don't see them winning the primary if either of them ran. They both might have gone #nevertrump in an attempt to be re-elected or they might have abandoned any opposition to him after he won like Gardner. Or they might have tried for governor in their respective states so they didn't have to worry about re-election. If they remained in the senate, they would both be headed for a loss.

[Roll Roons]

In 2014, Smith holds on by upper single digits and Coleman by around 10. It's possible that one or even both runs for president in 2016. Both would likely lose this year, though Smith would go down by a bigger margin than Coleman. I wonder how they'd vote on all the big ticket things (Gorsuch, AHCA, tax bill, Kavanaugh, removal), or if either would have supported a hearing for Garland.

[NewYorkExpress]

Obamacare (and pretty much anything else Obama attempted, possibly including most of his cabinet nominations) would be DOA, assuming Democrats don't junk the fillibuster.

Smith/Coleman might try to run for President in 2012 (Coleman is more likely to do it than Smith is).

As for 2014, I think Coleman loses (probably to someone like Tim Walz) while Smith narrowly survives, and probably retires in 2020.