As lawmakers prepared to take a risky and fateful vote on Obama’s plan to train and equip the Syrian rebels, the man who assured them it could be done was Gen. Michael Nagata, Obama’s point man for the mission to build an ISIS-killing army in Syria.

There are skeptics both inside and outside the government who doubt Obama’s new plan to arm the Syrian rebels can work. First of all, the administration has said for years that the moderate opposition can’t be a reliable partner for the United States in Syria. Only last month, Obama said that the rag-tag bunch of “former doctors, farmers, and pharmacists” could never win their civil war and the whole idea that arming them earlier would have made a difference has “always been a fantasy.”

Then Obama made a complete reversal, announced that portions of the Free Syrian Army were now vetted enough to help the U.S. fight against ISIS, and called on Congress to vote to give him authority train and arm them. Congress went along, but only after hearing from Nagata, who briefed both House and Senate members and staffers in classified settings and told them how he would get it done. Those briefed said they were impressed by the general but remained concerned that Obama’s plan was fatally flawed.

Nagata has experience in the area. U.S. military officials say Nagata helped devise much of U.S. special operations support for Jordan. These officials also say Nagata also has worked on plans with the CIA at the secret Jordanian base used to train Syrian rebels under the still secret but well reported joint DOD-CIA program that began in 2012. Nagata is currently in charge of special operations command for Central Command, the military command that includes Syria, Iraq, Afghanistan and Iran.

Lawmakers who have been briefed on the new Syrian train-and-equip program—which unlike the old one is entirely under military command as opposed to the CIA—raised concerns that it will suffer from the same flaws as the CIA program that began in 2012.

“They can show you lots of information on who they trained, where they came from and what kind of gear we gave them,” one lawmaker told The Daily Beast about the CIA training program. “But they can’t tell you what happens to them once they cross the border into Syria.” This lawmaker said this is because Obama has opposed embedding any U.S. personnel inside the opposition units once they are trained. “This is like throwing a bunch of guns over the border and saying, ‘Good luck.’”

So far, according to this lawmaker, the CIA has trained no more than 3,000 rebels since 2012 out of the Jordanian base.

Defense Secretary Chuck Hagel testified to Congress last week that the new Syrian rebel train-and-equip program will train around 5,000 rebels per year. Two senior congressional aides who were briefed on the plan said that each rebel training base will be able to churn out 1,800 rebels per year. There are two planned for Saudi Arabia and one planned for Jordan, although the Jordanian government has yet to sign off on hosting the site. The plan is designed to be scalable and more training bases could come in future years.

The hope is this time around, under the military training, the results will be different. But at least so far Nagata and other top U.S. officials have told Congress there is no plan to embed U.S. special operations forces into the Syrian opposition units once they are sent back into Syria.

There may be a reason for this. One congressional staff member told The Daily Beast that it is particularly sensitive to send U.S. special operations into Syrian territory in part because it would be a clearer violation of international law than bombing Syrian targets from the air. “Normally we are training up forces at the request of a host nation,” this staff member said. “This time we are training forces whose aim is to overthrow another country. That’s usually what the CIA does and not the military.”

Nagata himself has received very high marks from his former colleagues. James Mattis, who served between 2010 and 2013 as the commander of Central Command, said of Nagata: “You can count on him and he can stand and deliver.” Rep. Adam Schiff, a Democratic member of the House Permanent Select Committee on Intelligence, said, “I was impressed with him and he seems like a straight shooter.” One senior U.S. intelligence official said of Nagata: “He is one of our very best special operations warriors. There are no other commanders in uniform today with more time facing this threat than Mike Nagata. He is a strategic thinker with the tactical skills and judgment of the best leaders we have in our military.”

Well before he was in charge of special operations for the Middle East region, he held a series of progressively senior jobs at the highest levels of the part of the government where the military and the intelligence community intersect. His patrons throughout his career have been the leaders of the counterterrorism policies of the last six years, former CENTCOM Commander and CIA Director David Petraeus, former ISAF Commander Gen. Stanley McChrystal, and former Special Operations Command chief Adm. William McRaven.

“Nagata is in the generation of counterterrorism leaders that is following after McChrystal, Petraeus and McRaven and he is one of the leading minds in that world. He was a top deputy to all of these people,” said Robert Caruso, a former official at the office of the Special Inspector General for Afghanistan reconstruction. “If your intention is to train a force that’s going to just continue a stalemate and maintain a status quo in Syria, Nagata is not your guy.”

Already a rising star in the secret defense world, after the 9/11 attacks Nagata went to work for Stephen Cambone, the controversial undersecretary of defense for intelligence under Donald Rumsfeld. In 2005 he was put in charge of a “special mission unit.”

In 2008, Nagata was then tapped to join the Office of the Director of National Intelligence, where he served for one year as deputy director for counterterrorism before being chosen to be the head of the Defense Department’s office at the U.S. Embassy in Islamabad, Pakistan, a hugely sensitive post, during the time the Obama administration was reevaluating its Af-Pak strategy. He served there while McChrystal was in charge of the Afghanistan war.

In early 2011, shortly after Petraeus took over for McChrystal in Kabul, Nagata moved back to the Pentagon and took charge of all counterterrorism and special operations missions on the Joint Chiefs of Staff. He moved to Tampa to assume his current post last year, where he runs all special operations for SOCOM-Central, the highest profile job in that world because of the countries they are in charge of.

In an Oct. 20, 2013 interview with the Tampa Tribune, Nagata acknowledged that Special Operations Command was helping support a U.S. military effort to bolster Jordan’s defense. “Our role is to provide support, and mostly through training, helping train the special operations forces of Jordan, as a hedge against instability that might emanate from Syria,” he said.

Hagel testified last week that Nagata’s new mission will be much broader, and he indicated that it will be much more difficult.

“This is the beginning of a multi-year, scalable effort designed to eventually produce an even larger opposition force. The package of assistance that we initially provide would consist of small arms, vehicles and basic equipment like communications as well as tactical and more advanced training,” Hagel testified to the House Foreign Affairs Committee. “As these forces prove their effectiveness on the battlefield, we would be prepared to provide increasingly sophisticated types of assistance to the most trusted commanders and capable forces.”

Many lawmakers don’t see how training 5,000 Syrian rebels a year, assuming trustworthy, vetted brigades can be found, can defeat an ISIS army that the CIA estimates may already have 31,000 fighters and is growing.

“The goal is not to achieve numerical parity with ISIL, but to ensure that moderate Syrian forces are superior fighters trained by units,” Hagel said.

Even some lawmakers who support the plan don’t believe the administration’s claims that the Syrian rebels will only fight ISIS after being trained by the U.S., rather than focusing on their real enemy, the regime of Syrian President Bashar al-Assad. After all, that’s what the FSA is saying openly it plans to do.

“You don’t think that the Free Syrian Army is going to fight against Bashar Assad, who has been decimating them? You think that these people you're training will only go back to fight against ISIL?” Sen. John McCain asked Joint Chiefs Chairman Gen. Martin Dempsey last week during the Senate Armed Services Committee hearing. “Do you really believe that, General?”

“What I believe, Senator, is that as we train them and develop a military chain of command linked to a political structure, that we can establish objectives that defer [the Assad] challenge into the future. We do not have to deal with it now,” Dempsey responded.

“That’s a fundamental misunderstanding of the entire concept and motivation of the Free Syrian Army,” McCain said. “And that’s a fundamental fallacy in everything you are presenting this committee today.”