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On Thursday, the White House announced on Monday, President Obama and Russian President Vladimir Putin will formally meet for the first time in more than two years.

This meeting comes at a particular difficult time for President Obama as Russia has been gaining influence and leverage in the Middle East, especially as it relates to Syria.

In the past month, Russia has been pouring military equipment and personnel into Syria in its effort to shore up the regime of President Bashar Hafez al-Assad.

Now Russia has different motives then the United States as it relates to ISIS and Syria. Dmitry Adamsky wrote in “Foreign Affairs”, “Putin’s Damascus Steal” that Moscow is so eager to shelter Damascus because it is the Assad regime’s battle against ISIS (together with Hezbollah and Iran) that is keeping jihadists from swarming into Russia. With ISIS volunteers from the Caucasus, Central Asia, and Russia calling to bring jihad back home; with the Caucasian Emirate in southwestern Russia swearing allegiance to ISIS; with experienced veteran jihadists returning to Central Asia and North Caucasus; and with Chechens and Muslims, including radicalized Crimean Tatars, volunteering to fight in Ukraine, Moscow’s concerns are genuine.

Just because Russia wants a dialogue with the United States doesn’t mean Obama enters this meeting with a strengthened hand.  President Obama has his own challenges as it relates to Syria and ISIS and for that matter the broader Middle East.

Last week it was reported but not confirmed by the State Department, President Obama’s “War Czar” retired General John Allen will be stepping down as America’s effort against Islamic militants in both Syria and Iraq is floundering.

This comes at a difficult time for the president, as just last month incoming Marine Corps Commandant, Lieutenant General Robert Neller, testified at his confirmation hearing that the war is at a “stalemate.”

There have been reports General Allen had been frustrated with White House interference with the war and to prosecute the campaign with the vigor needed. It should be noted that the president’s war authorization he issued back in February has stalled in Congress, but the president has done virtually nothing to lobby for its passage.

“John Allen has put his heart and soul into trying to make the president’s strategy work,” said Derek Harvey, a former senior U.S. military intelligence official who worked with Allen at U.S. Central Command. “I have sympathy for the hard task he was given because I do not believe the president’s team was fully on board and he was never empowered to bring the leadership necessary to achieve the mission.”

The situation was made even worse when former CIA Director David Petraeus, and key architect of the surge of U.S. forces in Iraq in 2007, testified before the Senate Armed Services Committee, in which he stated Syria has become a “geopolitical Chernobyl” of extremism and chaos.

In his estimation the United States needs to act aggressively against the Assad regime in Syria, unfortunately this will place the president at odds with Putin.  Both view the situation differently, each with different strategic viewpoints.

President Obama placed himself in this precarious situation with his “redline” in 2011, that Assad time has come and he must go, the unfortunate aspect the president never articulated how this was to be done, and who would succeed Assad.

The situation inside Syria is the equivalent of a failed state, with various Islamic terror organizations operating throughout the country, and ISIS declaring itself a new Islamist “caliphate.”

The situation inside Syria is the result of failed secular governments, as we have witnessed all too well in Iraq, but the United States has lost leverage with many of our traditional allies in pursuit of a nuclear deal with Iran, at the expense of everything else.

Strategic missteps by the United States have placed Russia as a major regional power broker replicating its role it once played during the Cold War.

Adamsky continued to state, Moscow is likely to continue positioning itself as an indispensable regional middleman. Given its ties to Iran, Syria, and Hezbollah, and its cultivation of Egypt, Saudi Arabia, Jordan, and the UAE, Moscow has even started to build its potential as a Sunni-Shia broker.

Moscow has even been building commercial and military ties in the region unseen for decades, all at the expense of the United States. Far too often our traditional allies and our adversaries view the United States as retrenching from the region, as this has allowed Iran and Russia to exert greater influence and leverage.

The president enters this meeting with Putin, believing there can be a workable solution, but the Russian president views Obama has someone not committed to the region and only looking for a way out of the situation, with another country doing the heavy lifting.

The president has to be careful as any decision or agreement he makes will have ramification for decades.