A deep dive into the CNN archives highlights Trump's political dexterity over nearly three decades. To be fair, he has been on the GOP track for the bulk of that time.
In the late 1980s, during sit-down interviews with CNN's Larry King, Trump declared himself a Republican. And in an interview during the 1988 Republican National Convention, Trump agreed with a characterization of him as a Rockefeller Republican, a mid-20th century nickname for members of the GOP who were more sympathetic to liberal views on social and domestic issues. Trump has supported universal health care for a number of years, an issue typically tied to the Democratic platform.
The 1990s were shaky for Trump and his allegiance to the Republican Party. When he attended a Democratic congressional dinner in 1993, a reporter asked him if he considered himself a Democrat.
During a 1999 interview with King Trump discussed a potential presidential bid with the Reform Party.
"I think that nobody's really hitting it right. The Democrats are too far left," Trump said when questioned about his motivation for potentially leaving the GOP. "The Republicans are too far right."
While he did form an exploratory committee in 1999, Trump never launched an official campaign.
Trump's openness to Democratic policy approaches continued during the following years.
"You'd be shocked that if I said, in many cases, I probably identify more as Democrat," Trump told CNN's Wolf Blitzer in 2004
. "I mean, it just seems that the economy does better under the Democrats."
By 2011, though, Trump was openly declaring himself a Republican.
"I'm a Republican. I'm a very good Republican," he told CNN's Piers Morgan.
Four years later, he declared his bid for the 2016 Republican presidential nomination, which he is now poised to claim at the party's convention this summer.
Relive Trump's love affair with the GOP in the video above.