Perhaps the third time will be the charm.
At the United Nations General Assembly in 2017, his first as US president, Donald Trump nicknamed North Korea's Kim Jong-un “little rocket man”.
A year later Mr Trump said his White House had “accomplished more than almost any administration in the history of our country,'' a statement greeted by a mix of applause and laughter among the annual gathering of world leaders.
When the president takes the UN stage on Tuesday for this year's address he is likely to stick to superlatives when outlining his vision of America in the world. A more sober measure of his approach, however, is that after almost three years in office the Trump administration is still looking for a significant diplomatic policy achievement.
The US's unilateral stance on issues such as climate change, Israel and the Palestinian territories, its withdrawal from the Iran nuclear deal, and on North Korea, set Mr Trump apart from his predecessors.
Iran stands at the heart of US interests at the 74th General Assembly. Mr Trump's speech is likely to be dominated by it.
Were he to seek a broad consensus at the UN on how to tackle Tehran it would signal a significant change in policy.
Mr Trump's decision to abandon the nuclear deal, without an alternative agreement in place, remains opposed by its other signatories and is blamed by his critics for causing problems, rather than solving them.
On Iran, Mr Trump has shifted course, sometimes suggesting he wants to do a deal and indicating he is ready to talk to its officials, including President Hassan Rouhani. But Tehran has said sanctions must be lifted before there are any new negotiations.
Should Mr Trump seek greater diplomatic co-operation in the aftermath of the attacks on Saudi Aramco oil facilities he may be better rewarded, and find it easier to avoid a major conflict heading into a US election year.
“The maximum pressure campaign of sanctions has gotten us a damaged Iranian economy for sure but also an Iran that is lashing out in the region, threatening global energy security and rebuilding its nuclear programme,” said Richard Nephew, senior research scholar at Columbia University's Centre on Global Energy Policy.
“This has been done in a way that may soon prompt a new crisis all while limiting the chances of future diplomacy. It's not a shining success.”
So far, Mr Trump's leadership style has put him at odds with a founding principle of the 193-member UN: the concept of multilateralism.
Having initially mocked Mr Kim, the US president embarked on a personal charm offensive, meeting the North Korean leader at summits in Singapore and Hanoi and then again at the demilitarised zone this summer. But the process of reaching a deal, which relies on low-level talks on the detail of any denuclearisation process, stalled soon after the cameras had stopped clicking.
At the same time America's traditional allies Britain and France have criticised Mr Kim's resumption of missile testing – the initial cessation of which Mr Trump hailed as his achievement. Mr Trump has said he is “not worried” about Mr Kim's resumption of such tests but the gap between him and other world leaders has grown.
Similarly early in its tenure the Trump administration shunned the UN on Middle East peace, openly siding with Israel and refusing to state if the US remains committed to a two-state solution for Israel and the Palestinians. Mr Trump appointed his son-in-law Jared Kushner as a Middle East envoy and tasked him with crafting “the deal of the century”.
But the talks have been one-sided, with the White House moving the US embassy to Jerusalem, alongside other concessions such as acknowledging the Golan Heights as Israeli territory.
Another US Middle East envoy, Jason Greenblatt, twice berated members of the UN for their failure to end the dispute between Israel and the Palestinians. However, with the US plan edging towards shambles, Mr Greenblatt announced last month that he was quitting. The future of Mr Trump's main ally in Israel, Prime Minister Benjamin Netanyahu, is also in peril after a poor election result.
Such stasis is reflected at the UN, where the US is alone: all other 14 members of the world body's Security Council back the two-state solution.
Climate change, the UN's main theme of this year's General Assembly, is similarly defined by US isolation. Mr Trump attended Monday's climate summit for just 10 minutes and no US official spoke at the event.
But while many countries have trodden carefully around Mr Trump's declared intention early in his presidency to withdraw from the climate accord – he personally has applauded coal as a source of energy – this year's General Assembly signals a change, according to Richard Gowan, UN director at the International Crisis Group.
“UN Secretary General Antonio Guterres got world leaders to buy into this summit despite the fact the US is, at best, disengaged,” said Mr Gowan.
“In 2017 and 2018, there was a sense that many leaders were tip-toeing around President Trump at the UN, trying to avoid raising any topics that might irritate him.
“This year they have decided to go ahead without the US. That could be a very significant turning-point in multilateral diplomacy, as other states decide to work together without US leadership.”