“It is true that when you run to succeed a two-term president of your own party, you have a historical headwind blowing against you,” Clinton told Hewitt.
Tell that BS to Bush Sr.
Not if you succeed a successful president.  Then you're a shoe in.   That's why Bush Sr. got in and Hillary didn't.  Reagan was successful and Obama was a failure.    Bush Sr. was a failure,  that's why he got turned out.   That's actually quite rare to not get a second term now,  even Barry managed to pull it off even after failure after failure. 
It only looks like a headwind because most presidents are failures for the most part.