Challenge: President Douglas

No Lincoln will not work. The Democratic Party had fractured before the Republicans even nominated a candidate. For Douglas to win he needs to avoid that party split and pull a significant number of people who voted Republican in OTL. Either of those would at best be unlikely.

Plus Douglas died in 1861, before the Battle of Bull Run in OTL.

You've got a much better chance of Douglas becoming President in 1852 or 1856. In 1852, Pierce was a dark horse who didn't win the nomination until the 49th ballot. In 1856, Buchanan was the frontrunner for the nomination. After a weak start, Douglas steadily gained, but was still behind and eventually withdrew after the 16th ballot.

1852 seems the most likely to me.
 
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