Obama was young and completely inexperienced. He was a one term senator with no background as an executive in any capacity. He had zero experience running or managing anything. Then he spent the next 8 years on talk shows, and saturating the twittersphere.
Love him or hate him, Trump at least has executive experience, and as I said, after the current President downgraded the office through his own choices, Trump was the next logical step in the regression.