So far, Trump has never won any elections in his life. And this is not the first time he is running for president. Reform Party anyone?
The Illinois senate race was essentially handed to him by getting his only credible opponent to resign by leaking sealed court records. His primary was one by similar tactics. So was his election to the state legislature, though I believe the tactic differed slightly by getting his opponent disqualified from the ballot.
When did Trump ever run for president before?