He's already winding him up mercilessly. The context is that Putin's very substantial and prickly pride has been deeply wounded by being flatly ignored and personally banned by the entire western world for several years, and that his travel and international interlocutors are constrained to China, Iran, North Korea and, errr, back to China again. He is absolutely desperate to be out on the World Leader circuit again, as fast as possible. And in his optimistic moments his hopes are high.
Now, nationalist Russian sentiment is aggrieved - and is certain Putin is also angry - that Trump has failed to recognize with sufficient gratitude that Soviet Russia won WW2. They say Putin will assuredly give Trump one of his "history-lesson" rants whenever they do finally get to talk. He is given to rants of this kind: lengthy and rambling with a mind-numbing effect on audiences. Nobody outside of the aforesaid China, Iran and N.Korea is trained to "listen attentively" to these things any more: the days of Fidel Castro at the podium are a distant memory.
And in Trump, they have truly misread their man.
For all his gargantuan failings in many departments, Trump has a colossal amount of low cunning in the matter of personal encounters and human psychology. Both he and Putin have made vast capital from their differing abilities in human engagement, so they both operate psychological theories of a kind. But mano a mano? When dealing with anyone other than meet-the-people walkabout audiences, Putin self-evidently relies on pure menace and intimidation - he even considers this a matter for pride and the TV cameras - a very Russian thing. Look at the merciless, gleeful, premeditated way he literally set dogs on Angela Merkel, a well-known cynophobiac. It'll be water off Trump's back: the man doesn't give a toss for such things (and probably won't even grant a face-to-face meeting). But having already been baited, can we see anxious, urgent Putin going for everyone else's Plan A, viz abject flattery? Really?
Both Putin and Trump are of course themselves the subjects of endless psychological analysis and speculation, professional and amateur. But you know who can play them both? Well, maybe Xi, who has the luxury of considering his chess-by-post moves very carefully, and never needs to make a move he's not totally comfortable with. But Xi is unlikely to hold the key to restoring Li'l Volodya's fortunes in the Big World of Global Prestige.
The relevant answer is ... Zelensky. If you've seen one or other of the lengthy TV documentaries on the man, you'll be in no doubt whatever that the little comedian / showman / war leader is absolutely masterful in his personal dealings - with whole crowds of foreign politicians as well as one-on-one encounters. He, too, has had a very long time to ponder the arrival of Trump, but his conclusions and plans for this critical juncture will have been a lot more adroit than the twisted frettings of Putin. I'd rate Zelensky's chances quite highly of making a bit of strategic hay over the next couple of months.
On the other hand I doubt very much that Putin's upside scenario - Transactional Trump the famous isolationist, wants a quick PR win, and gives me everything I want - will play out anywhere other than in his most optimistic dreams. The downside - still in the global naughty corner come summer, Ukrainian drones still falling nightly on my oil refineries, and another trip to Pyongyang in the diary - looks a lot more likely.
And Zelensky will still have a ghastly, grinding war on his hands. Perhaps with a few more weapons in the armoury, though. And Xi will continue to sit there quietly at his own global chessboard, planning his Taiwan campaign.
ND