The Obama administration is worried that Putin is about to pull a fast one in New York
White House officials are reportedly trying to decide whether the two leaders should meet to "work out their differences before the tumult in the Middle East escalates even further,", according to The New York Times.
Some in the administration, however, "worry that agreeing to meet would only play into Mr. Putin's hands and reward an international bully," The Times reports.
Obama has declined to meet with Putin since Russia annexed the Ukrainian peninsula of Crimea in March 2014. The trip to address the UN will mark Putin's first visit to address the assembly in 10 years.
Putin has made it clear recently that he wants to get back on working terms - Obama said he was "encouraged" by a July call with Putin about Syria, and Russian Foreign Minister Sergei Lavrov said in August that Putin would "consider constructively" any request for a meeting with Obama at the UN assembly.
Putin also recently expanded Russia's military footprint in Syria, sending elite soldiers, pre-fabricated housing for at least 1,000 people, a portable air traffic control system, and other items that could be used to create an air base for forward combat operations to help prop up the embattled regime of Syrian President Bashar Assad.
The Kremlin, which has offered military-to-military talks with US on Syria, might be using this as leverage to force the US to cooperate.
"[People think] that what Russia is doing in Syria is forcing its way through to the negotiating table with the US on Syria," Dmitri Trenin, director of the Carnegie Moscow Center think tank, said on a call with reporters on Wednesday. "The Russian diplomatic strategy is to be taken into account by the US."
Putin might be hoping that because Ukraine and Syria are two of the most significant conflict zones in the world, the US will decide that the only path to a solution is to work with Moscow.
And at the assembly, Putin will reportedly continue making the case for Russian involvement in the Middle East.
"The Kremlin has far-reaching goals for that speech," Russian military analyst Aleksandr Golts wrote in an article cited by the Times.
"It hopes that the process of forming such a coalition would free Russia from its international isolation caused by its annexation of Crimea and the war in eastern and southern Ukraine and also make it a respected member of the world community again."
Consequently, the Obama administration fears playing into Putin's game.
"I think at this point the White House never wants to look like it's scared into a meeting," Andrew Weiss, vice president for studies at the Carnegie Endowment for International Peace, said on the Wednesday call. " The proper response is to have a clear point of view for what we want in Syria."
That might be easier said than done, as Obama has been criticized for his inaction in Syria. Despite calling for Assad to step down, the US has not intervened militarily in Syria to oust the dictator.
Columnist Roger Cohen pointed out in the Times this week: "American interventionism can have terrible consequences, as the Iraq war has demonstrated. But American non-interventionism can be equally devastating, as Syria illustrates. Not doing something is no less of a decision than doing it."
Assad, who was interviewed by Russian media this week, has been barrel bombing Syrian citizens, creating a huge outflow of refugees who are now fleeing to Europe.
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As the crisis spreads through Europe and Russia continues to support Assad, Russia could also be positioning itself for the diplomatic end to a civil war the US wants.
And Putin could use his leverage with Assad to broker a deal that sees Russia having a hand in deciding who succeeds the Syrian leader.
"Putin has been trying desperately to communicate that he's a force to reckon with on the international stage," Weiss said. "He wants to look like he's important on the top table of international dealings."
David Rothkopf, CEO and editor of the group that publishes Foreign Policy magazine, predicts that the US will strike a deal to grant Assad immunity, let Russia and Iran dictate what happens to the regime, and then focus fully on ISIS and al Qaeda in Syria.
This would be a good deal for Putin, who defends his support of Assad by saying that his regime is fighting terrorists, including the extremist group ISIS and the al-Qaeda franchise in Syria, the Nusra Front.
But this ignores the fact that when the Syrian civil war first started in 2011, Assad intentionally infused his opposition with the extremists his regime now claims to fight while seeking to destroy the national rebels comprised of Syrian Arab Army defectors and civilians taking up arms.
Michael B. Kelley contributed to this report.