Woodrow Wilson - After the 1912 election, nothing really went his way. Isolationism was a great policy and all, but he allowed Germany to sink so many of our ships and failed to negotiate peace talks. Then after declaring war which he really didn't want to do to begin with, he got even more hate from citizens of German, Austrian-Hungarian, Bulgarian or Turkish descent and also in part due to the 18th Amendment, his party lost control of Congress to the Republicans which really changed the outcome of what could have been Wilson's greatest U.S. accomplishment. Congress went against his proposal at the Treaty of Versailles for a League of Nations and President Wilson ended up getting paralyzed from campaigning across the country to hard for it which ended his political career and never got to run again in 1920.
Wilson was no isolationist. He was an Anglophile who was dealing with a traditionally isolationist public but who was consistently as pro-Entente as he could get away with. His sham neutrality is what allowed him to eventually draw the United States into the war when it became clear that without American troops and money, the Entente would lose the war.
If anything, Wilson should be considered one of the luckier U.S. politicians. Without the Republican infighting in 1912, he never would have gotten to be president. Without the European fighting in 1916, it is doubtful he could have ever gotten reelected.
Notice I said "after the 1912 election" because yeah, he did get lucky in that sense. Roosevelt had a lot of support in the northeast (especially New York) plus out west (Oregon, Montana, Nevada etc.) and if it hadn't been for Taft being in the way, Wilson wouldn't have won in the landslide that he did and for all we know, Roosevelt could have pulled out a victory over Wilson with a united Republican Party pulling out victories in the solid North at the time.
As for 1916, Wilson wouldn't have won if it wasn't for his pacifist, but pro-Allies, policy. Although his neutrality clearly failed, he still barely won with "He kept us out of war" and "Peace without victory" and gained large public appeal for it. If Wilson had declared war on Germany before the election, Wilson most likely would have lost California's 13 electoral votes which would have given Hughes the win. So I'll agree with you partially that his early career as Princeton President, Governor of New Jersey, the 1912 election, "New Freedom", or the Federal Reserve was pretty good, but after 1914, everything went downhill from his first wife's death to passing the "Political Suicide Amendment" to the Democrats losing control of Congress to nearly losing his life!
