I think he wins the electoral easier then the popular votes. He easily takes Virginia, Florida and Ohio. That is game set match. Anything else in the purple column is gravy.
You need to read the article. He is suggesting that the state legislatures take back the role of appointing the electors themselves, rather than use the popular vote, and then appoint electors who would vote for a 3rd candidate in the Electoral College, denying any of the candidates a majority. The election would then go to the House, with each state getting one vote. They can only choose among the top 3 electoral vote recipients. It is unorthodox, but would be constitutionally permissible. SCOTUS has already held that the state legislatures can choose whatever method they like to appoint the electors, and the federal courts have no say in the matter.