Owen Poland worked as TV3's business editor in 1993 when he interviewed Donald Trump in Auckland.
He got four minutes with Mr Trump and looking back, Mr Poland has one regret.
"I should've asked him if he'd ever consider running for president. That's what I should have asked him 23 years ago," says Mr Poland.
The business tycoon-turned US presidential candidate was only in the country for a whirlwind 10 hours, to discuss a proposed casino partnership with Auckland iwi Ngati Whatua.
"It was a big deal for me at the time. It was the first time he'd come to New Zealand and being such a powerful global businessman, I was really excited," says Mr Poland.
"He was engaging, he was friendly. He was charming, he was upfront."
Mr Poland also asked Mr Trump about his personal image as tycoon and as a womaniser, his divorce with Ivanka, and his enormous debts.
"I was interested to know about the real Donald Trump and about his marital issues [...] He was a womaniser and 23 years ago, it wasn't such a big deal," says Mr Poland.
He says he's surprised Mr Trump chose to go into politics and says the antics of his youth have "kind of come back to haunt him".
"Given all the skeletons in his closet, you'd think he would have known better than to do this because sooner or later, once you get into the dirty game of politics, all that stuff is going to come out," he says.