Heilemann on Trump: What's his end game?

Story highlights

  • John Heilemann is co-managing editor of Bloomberg Politics
  • He says regardless of the result on Election Day, Washington will have gridlock

The Axe Files, featuring David Axelrod, is a podcast distributed by CNN and produced at the University of Chicago Institute of Politics. The author works for David Axelrod.

(CNN)As Donald Trump decries a "rigged" electoral process in the face of his sliding state and national poll numbers, the most interesting question now might be whether he is trying to win the election or get a good return on his investment, according to Bloomberg Politics' co-managing editor John Heilemann.

"Does he know that he has probably lost?" Heilemann, who is also the best-selling author of Game Change, wondered aloud to David Axelrod on "The Axe Files" podcast, produced by the University of Chicago Institute of Politics and CNN.
"Are the things he's doing now designed in a really, really cagey -- and also kind of diabolical -- way to build an anti-Clinton coalition that he can monetize through another business venture after this is over? Is that his end game now?" Heilemann said. "Or does he actually believe that there are all these uncounted millions out there who are going to rise up on Election Day and prove all of the polls wrong?"
    Heilemann confesses to not knowing the answer, but said he is fairly certain that no matter the outcome, this election portends continued gridlock in Washington.
    "Put aside the questions of, 'are you undermining the fundamental tenets of American democracy?' which I think [Trump] may be in some respects," Heilemann said. "Just ask the question, 'What's it going to be like to have to govern?'"
    Heilemann suggests looking to the 2008 election and its aftermath for a clearer picture of exactly what kind of Washington will greet the next president.
    President Barack Obama came into office, Heilemann said, "after a relatively unifying election...and then giving a speech in Grant Park that was magnanimous and big," only to find an uncooperative Republican Party "ready to undermine him from the moment he walked in. Think about how much worse it will be for her now."
    Pondering this scenario, Heilemann concluded, "the problem will exist and potentially will exist times 10."
    To hear the whole conversation with Heilemann, which also covered his chance meeting in the 1980s with Obama while both were students at Harvard, his short but momentous stint as a political aide, and why his personality traits were ultimately better suited to journalism, click on http://podcast.cnn.com. To get "The Axe Files" podcast every week, subscribe at http://itunes.com/theaxefiles.