Their last meeting in Helsinki seven years ago is remembered by Trump siding with Putin and contradicting US security agencies about Russia interfering in the 2016 US presidential election.
"President Putin says it's not Russia. I don't see any reason why it would be," Trump said at the time, provoking anger in his home country because he had turned his back on his country's most important security agencies after just one personal meeting with Putin.
When it comes to the American president's readiness for meetings at this level, things are not looking much better ahead of Friday's meeting with Putin in Alaska.
Everything leading up to the pre-arranged meeting suggests that we can once again expect surprising news. Unpredictability once again follows the organisation of a meeting from which the world expects, if not a solution, then at least an important step towards peace in Ukraine after three and a half years of Russian invasion.
Two days prior to the meeting, there is still as much uncertainty surrounding many crucial aspects of it as there was when Washington and Moscow initially announced it.
Self-proclaimed talent for making deals
President Trump seems to be announcing the second part of the 2018 Helsinki meeting with Putin, as he is travelling there with much more confidence than with a precisely worked-out negotiating strategy.
It seems as if he is once again relying solely on his personal "deal-making" abilities and not on the recommendations arising from the security and diplomatic analysis of the world's most complex crisis in recent decades.
"We're going to have a meeting with Vladimir Putin, and at the end of that meeting, probably in the first two minutes, I'll know exactly whether or not a deal can be made," Trump said on Monday. When asked how he knew that, he replied, "Because that's what I do. I make deals."
Trump once again seems to be going into a super-important meeting without any thorough diplomatic preparation
His assurance that it will take "the first two minutes" is reminiscent of the announcements from the election campaign that he would end the war in Ukraine within 24 hours.
What's more, if he estimates in these first two minutes that a deal with Putin is possible, then Ukraine and all its partners should really be afraid of what the American president has accepted.
Because apart from his self-proclaimed talent for making deals, Trump once again seems to be going into a super-important meeting without any thorough diplomatic preparation.
The centre from which the confusion is spreading
Trump's special envoy for Russia, Ukraine and the Middle East, his friend and entrepreneur, Steve Witkoff, seems to be the centre from which most of the misunderstandings about the summit are emanating.
Even more alarming is that this businessman with no diplomatic experience whatsoever serves as, if not the only, then the most important source of information and estimates for the American president.
And what Mr Witkoff brings to the White House as input after his diplomatic trips can hardly be described as information and assessments. It is rather a mix of personal impressions and misunderstood messages from a confused and manipulated man.
It took several days after Witkoff's last meeting with Vladimir Putin in Moscow to sort out the confusion about what Putin had really said.
The seemingly simple mission of delivering and receiving messages that Mr Witkoff undertook in the Kremlin last week has turned into a mess, due to the inexperience and self-confidence prevalent in Washington.
Nothing seems to have been clear for Mr Witkoff when he left the Kremlin
Mr Witkoff did not understand or remember what Putin told him at the meeting about what he would demand in negotiations with Mr Trump over the occupied parts of Ukraine. European leaders' insistence brought some clarity to the confusion surrounding Mr Witkoff's interpretation of the conversation with Mr Putin.
Who is withdrawing, the Russians or the Ukrainians? Where are they withdrawing from - Donetsk, Zaporizhzhia, or Kherson? Nothing seems to have been clear for Mr Witkoff when he left the Kremlin. However, for Mr Putin and his associates, everything was clear, and they got exactly what they wanted.
They got a solo negotiator without the support of the US diplomatic apparatus, Mr Witkoff, alone at the meeting, just like in April at the previous meeting in the Kremlin.
Then the guest from the US came alone, while next to Putin sat his experienced advisors - Yury Ushakov and Kirill Dmitriev (and probably a large team of experienced diplomats and intelligence officers behind the scenes).
Amateur hour
Steve Witkoff has caused confusion in other extremely important negotiating situations. After his talks with Iranian negotiators in April, it remained unclear whether the US would allow Iran to maintain a certain level of development of its nuclear programme or demand its complete elimination.
You can't have him (Trump) and Witkoff winging it because they just don't know enough - Daniel Fried
"You can't have him (Trump) and Witkoff winging it because they just don't know enough. You need somebody in the room who can just look at the president, roll his eyes and shake his head," said Daniel Fried, a former senior US diplomat, before the summit in Alaska.
That is unlikely to be the case in the forthcoming talks between Trump and Putin, just as the American team was not well prepared for the previous talks.
Fiona Hill, an American expert on Russia and Putin who has attended previous meetings between the two leaders as a member of the delegation, told Foreign Affairs that Trump is unprepared for the meetings with his Russian counterpart and overly fixated on personal interactions rather than diplomatic strategy. "All of this is amateur hour," she said.
Another seasoned diplomat, Michael McFaul, the US ambassador to Russia under Barack Obama, suggests simple solutions: "This is deeply damaging incompetence. Witkoff should finally start taking a note taker from the US embassy for future meetings. That's how professional diplomacy works."
Perhaps it is too late for good advice before the meeting between Trump and Putin in Alaska.
