First, he fired his transition director, former New Jersey Gov. Chris Christie, and then once in office, he failed to push through promised changes to Obamacare. His travel ban on suspected terrorist-supporting nations faced several court challenges.
Just as bad, some of his Cabinet and picks for top aides flopped.
But as he looks at a possible second try should he beat President Joe Biden in November, expectations are high that he will better prepare to manage the Oval Office, begin the transition sooner, and test his initial policy moves way before Inauguration Day.