"I actually saw great potential right across the street, to be honest with you," he said during his first event at the United Nations General Assembly, an event he'd previously regarded mainly for its offensive emerald marble.
He was referring to the Trump World Tower building, erected directly across the street from the UN complex, with a view over the garden toward the East River. When the sun shines through the smoked-glass facade on late summer afternoons, an orange glow descends on Turtle Bay.
As world leaders gather this week for the yearly diplomatic confab, two New York institutions are converging. The United Nations and Trump are intrinsically connected to the city, both dotting the skyline and enmeshing themselves in the fabric of the city.
Spending the longest stretch of time in his hometown since taking office in January, Trump is basking in the attention of an institution he's spent the past decades observing only from the outside. On the occasions he attempted to insert himself into the body's affairs, he was roundly rebuffed.
Trump, who rarely forgets a slight, could find vindication after the past rejections this week, as diplomats angle to shake his hand or take his photo in the crowded corridors of the UN headquarters.
Before he became president, Trump had visited the UN in a business capacity, pitching himself to renovate the aging modernist building when it came due for refurbishment in the early 2000s.
Photos from a 2001 meeting with Kofi Annan, then the secretary general, show a 54-year-old Trump deep in conversation, situated in a wood-paneled office inside the headquarters building. A second photo shows Trump, his hair askew, stepping into his limousine outside the glass entryway.
He was passed over for the job, which infuriated the billionaire developer, who'd by then made his name as New York's most famous (and infamous) real estate magnate.
He dedicated an entire subsection of his book "Think Like a Billionaire" to the episode, decrying Annan as an "incompetent" who "has created a fiasco out of one of the world's most valuable institutions."
"Who is in charge at the United Nations?" Trump inquired in his book. "Could they be as incompetent in world affairs as they are at simple numbers? Does anyone else find this situation as alarming as I do?"
He testified before Congress at the invitation of Sen. Jeff Sessions -- now his attorney general -- saying he could have accomplished the job for hundreds of millions dollars less than what it ultimately cost.
Nearly a decade later he still appeared unsatisfied with the building's appearance, scoffing at the iconic emerald marble on the speaker's rostrum inside the General Assembly hall.
"The cheap 12 inch sq. marble tiles behind speaker at UN always bothered me," he tweeted in 2012. "I will replace with beautiful large marble slabs if they ask me."
It wasn't his first skirmish with the UN. Several years earlier, diplomats posted at the institution's headquarters balked at Trump's plans to construct the tall, skinny Trump World Tower just across First Avenue from the headquarters building.
Their concern: the building would cast unpleasant shadows over the iconic modernist UN complex, which had enjoyed its sunny perch on the far east side for decades.
Annan griped that Trump should never have been granted a building permit for the tower, which for a short period was the tallest residential complex in the world. Trump was defiant, insisting that Annan and his fellow diplomats would love the building once it was complete.
Legal challenges were unsuccessful, and today Trump's building stands across the street from the UN garden and a Soviet statue depicting St. George slaying a dragon, titled "Good Defeats Evil."
Speaking 200 yards away during his remarks on Monday, Trump was uncharacteristically diplomatic about the whole affair.
"It was only for the reason that the United Nations was here that that turned out to be such a successful project," he said.