And when those risks resulted in the deaths of Utah native Brandon Thomas and Colorado-born contractor Todd Venette, the families claim, Feeney failed to honor promises to pay out hundreds of thousands of dollars in life insurance.
On Thursday, four days shy of the two-year anniversary of the Baghdad killings, the families filed suit against Feeney in U.S. District Court in Salt Lake City, alleging wrongful death and breach of contract.
In doing so, they have found themselves splashing about in murky legal waters. Though some observers expect many such claims may follow, only a few have moved forward so far.
"This is a brand new legal area," said Scott Silliman, the director of the Center on Law, Ethics and National Security at Duke University. "The closer you get to the combat environment with civilians, the more vague and uncertain the rules are."
And in an age of increasingly privatized warfare, those rules still are being written.
There may be as many as 100,000 civilian contractors operating in Iraq, with a third or more working in a gun-toting capacity. Depending upon whom you ask, companies like Feeney's CTU Security Consulting Inc., are protected from litigation under federal law or they're not. They're liable under tort laws in the U.S. states in which they're based or they're not. They're subject to the Geneva Conventions or they're not.
The few laws that do exist haven't been thoroughly tested. A provision slipped into a defense spending bill in January, for instance, would permit military courts to try civilian contractors accused of wrongdoing in war zones, but challenges to its constitutionality - by everyone from the ACLU to conservative interest groups - abound.
At least 150 American contractors have been killed in Iraq and dozens more in Afghanistan. Silliman said he believes many potential wrongful death plaintiffs are waiting to see what happens in a few "test cases," including two filed against Blackwater USA, which has lost at least 25 employees in Iraq and arguably is the most well-known private security firm in the world.
For its part, Blackwater has staked its legal future on the controversial contention that it is exempt from litigation under the same federal laws that prohibit suits against the military. It also has produced, as evidence of its inculpability, broadly written liability waivers its employees sign before moving "in country."
Blackwater failed in its initial efforts to have one case - brought by the families of four contractors who were attacked, burned, dismembered and hung from a bridge in the volatile Al Anbar Province - dismissed based upon such waivers. Still, Silliman said, the documents signed by the so-called "Fallujah Four" - in which the men accepted all risks from working under "volatile, hostile and extremely dangerous circumstances" - may come into play as the case progresses.
"The biggest hurdle is really finding some kind of action by the employer that violated the provisions of a very tough contract," Silliman said.
Lawyers in Utah may have a whole different set of problems. Feeney told The Salt Lake Tribune he plans to challenge the jurisdictional authority of the suit, noting that Thomas and Venette worked for CTU Asia - a company registered in Hong Kong.
"First and foremost, none of these guys worked for the U.S. company," Feeney said. "These guys were never paid by any company but CTU Asia."
And proving that a contract was broken may be a complicated task, because CTU officials have told the families that they can't locate any paperwork for Thomas and Venette.
That didn't come as a surprise to one former Feeney employee, who still does contract work and asked not to be identified, said the famed warrior "operates his businesses on hand shakes, cash and offshore bank accounts."
Nor does it surprise Thomas' mother, Carol Thomas Young, who found it a little "too convenient" that there was no written record of promises she believes Feeney made to her son. Young is convinced that CTU promised her son $250,000 in life insurance.
"Brandon told me, 'Mom, I don't have any health insurance, so we'll have to pray I don't get sick, but there is a life insurance policy,' " Young said. "He was very adamant about that point. He even called me to get his brother's Social Security number to add him as a beneficiary."
Venette's parents say they had a similar conversation with their son, who joined Feeney's outfit a year earlier and told them he'd been promised $150,000 in life insurance.
Feeney said he didn't recall having any such conversations with the men in his company.
"It wasn't talked about," he said. "And furthermore, I don't think they cared. Everyone who does the job that we do knows the risks involved. You make good money and you stash it away for a rainy day."
After the bombing, CTU placed a memorial to Thomas and Venette on its Web site (it got the spelling of Venette's first and last names wrong.) Feeney also attended Venette's funeral, but soon after he cut off contact with both sets of parents, choosing instead to communicate through an intermediary.
Young, a retired deputy U.S. Marshal from Murray, said the fact that she wasn't hearing directly from Feeney - who hadd hired her son personally - made her suspicious. She grew more wary as she tried to track down the money her son, who was making about $10,000 a month, had been paid before his death.
"They told me that he had been carrying $20,000 with him in cash," Young said, "and that it all burned up in the explosion."
Dave Cassler, a contractor who suffered brain injuries in the attack that killed Thomas and Venette, said he found it disturbing that a man "who was always saying, 'your handshake is good enough for me,' " quickly placed an intermediary between himself and his employees after the bombing.
"It really seems like he was just trying to protect his own ass," said Cassler, who now lives in Mississippi and has built a friendship with the families of the contractors who were killed in the attack. "When you involve middle men, it gives him plausible deniability. When his promises fall through, he can just say, 'well, the middle man got it wrong. He screwed you over, not me.' "
Cassler said he still believes CTU does things better that most other security companies in Iraq. But from a man who lost part of his skull and still has shrapnel embedded in his brain from the bombing, the words may be more of an indictment of the security contracting system than a defense of Feeney.
Cassler said Feeney was an expert on keeping security contractors - and their clients - alive. In Iraq, CTU was broadly known to be one of the most innovative security companies when it came to moving high-profile clients through the war zone - mostly through the use of armored cars designed to look like common Iraqi taxis.
But Cassler also said Feeney was willing to live more dangerously when money was on the line. On the day Thomas and Venette were killed, Cassler said, it was not Feeney "or any other security expert" that made the decision to travel in a conspicuous convoy of beefy sports utility vehicles. The detail had been dispatched to pick up a few highly placed officials from Halliburton subsidiary KBR.
"The ultimate decision came from what KBR wanted," Cassler said. "Don Feeney said this is a bad idea and he fought with KBR on it a lot of times, but it all boils down to what KBR wants, KBR gets, because KBR is paying the bill."
Feeney said "it's no secret" that he preferred to travel in less conspicuous vehicles. He confirmed a few "epic" arguments with KBR over that fact. But Feeney also noted he wasn't physically present in Baghdad on the day on the bombing. And even if he had been, he conceded, it's possible he would have let KBR officials have their way.
"They asked for an extra-high profile detail. It was their call," he said. "We were being paid and it was our job to do it."
KBR, which owned the contract with CTU for providing protected transportation for company officials, has not been named in the Utah suit. Lawyers for the families, however, have named 10 "John Does" - leaving open the possibility that the plaintiffs may crawl up the chain of command seeking responsibility.
"We want to get the contractual relationships and the operations procedures under which Feeney was told to operate, because he was being hired by others," said Salt Lake City attorney Don Winder, who brought the suit on behalf of the families.
Winder acknowledged the difficulties of blazing new legal trails but said contractors like Thomas and Venette have gone far too long without knowing their legal status, rights and obligations.
"This war wouldn't be fought without these contractors," he said. "What kinds of protections are out their for them? We're going to find out."