An undercover ATF agent says infiltrating the Hells Angels led to 20 separate attempts on his life

Former ATF special agent Chris Bayless told former Navy SEAL and podcaster Shawn Ryan that his undercover work around outlaw motorcycle gangs placed him in the middle of a violent conflict where, by his later count, there may have been about 20 separate attempts on his life.

Bayless, appearing on the Shawn Ryan Show, described a period when he was working around organizations tied to the Hells Angels and the Outlaws, while murders, bombings, and retaliation plots were unfolding around him. Ryan asked Bayless about the close calls he experienced during that time, and Bayless said there were probably three he knew about while he was still working the case, but roughly 20 altogether when he later learned what had been happening around him.

That number is difficult to process because Bayless was not describing risk in a general sense. He was talking about moments when people were allegedly waiting outside his apartment, watching his movements, or preparing to attack him while he rode with club members.

Bayless said he eventually came to see those years with a kind of humility he did not have at the time, because he had believed he was more aware and more in control than he really was.

“I thought I was that,” Bayless told Ryan, before explaining that he later realized he had no idea how many times danger had come close without him seeing it.

The Violence Around The Case

The section of the interview began with Bayless describing a murder connected to the outlaw motorcycle world he had infiltrated, including the killing of a man named Monty.

Bayless told Ryan that he did not see Monty being killed, but he later saw the scene, saw photographs, and interviewed the man who killed him. He described the attack as especially brutal, saying the shooter entered and fired three times with a .45, but Monty did not go down and instead fought back.

According to Bayless, the man who killed Monty told him that Monty came around the counter, engaged him, got the gun turned around, and managed to squeeze off rounds before the fight moved deeper into the shop. Bayless said the gun eventually went empty, and the fight turned into a physical struggle.

The details Bayless gave were grim. He said the attacker later used a chunk of metal from a workbench to crush Monty’s skull, and when Monty continued fighting, the man ultimately used a screwdriver to kill him through the neck.

Bayless was careful in how he spoke about Monty, saying he was not trying to glorify anything, but that he appreciated Monty’s “fight for survival” in the final moments. That is a striking comment because Bayless was an undercover federal agent investigating people in criminal circles, yet he still reacted strongly to the brutality of what happened.

He told Ryan he was angry after seeing the aftermath, even though Monty was someone he may eventually have had to help arrest if the investigation supported it.

“We Can’t Cover You Enough”

Bayless said the violence around the investigation had reached a point where ATF management grew concerned that the risk could no longer be controlled.

He told Ryan that by then, they had information about gun storage, smaller narcotics and firearms buys, and useful conversations that could help outline a criminal enterprise for a possible RICO case. But management, as Bayless recalled it, told him they did not believe they could “cover” him enough to keep him from getting killed.

According to Bayless, the concern was that he was now in the middle of a war between the Outlaws and the Hells Angels, while also carrying the added risk that some members of the Outlaws might recognize him from prior work. He said there was also the possibility that people inside the club could decide he was the source of information leaking out, especially because he was a newer face.

Bayless admitted that at the time, he did not want to see the danger clearly. He said he had a .45 in the back of his pants and thought he was “super cool,” but looking back, he recognized that he was not as secure as he believed.

That kind of admission gives the interview much of its weight. Undercover work is often shown as controlled and strategic, but Bayless described a world where confidence could become its own hazard, especially when violence was moving faster than the case.

He said ATF management’s decision to pull back was ultimately the right one.

Pulling Out, Then Building The Case

Bayless told Ryan that after Monty was killed, he and the informant eventually backed away from that part of the undercover operation.

He said they explained to the people around them that their business was ruined and that everyone was trying to kill them, which gave them a way to exit without simply disappearing. Bayless said one of the men told them they could not come back, and they accepted that as the undercover portion ended.

From there, Bayless said he moved into a Grim Reapers case in the Quad Cities for about 15 months, while still helping build the larger RICO case involving the Outlaws and the violent acts connected to murders and bombings.

He also described how the informant later got back in with the group and helped federal authorities track additional planned acts of violence. Bayless said there were nights when members would say they were going “hunting” for Outlaws, and he would alert state police.

According to Bayless, law enforcement would then place marked and unmarked cars nearby, wait until the group appeared to be moving toward something, and stop them under the appearance of routine traffic enforcement. He said several of those events were later charged in the RICO case as acts they had been able to interrupt.

That is one of the more interesting parts of the interview because it shows undercover work not only as evidence gathering after the fact, but also as a way to prevent violence before it happens. The arrests and prosecutions matter, but in Bayless’ telling, so did the nights when a planned attack never reached its target because police were already in place.

Close Calls He Did Not Know About

When Ryan asked what close calls Bayless had with the Hells Angels, Bayless said the most disturbing ones were not the few he knew about at the time, but the many he learned about later.

Bayless said Sandy, who helped put together the RICO case, later asked whether he knew people had been outside his apartment. He said he did not. When he spoke with a cooperating witness, the person confirmed that they had been there.

Ryan asked why they were at his apartment, and Bayless said they were there “to kill us” because he was part of the group they were targeting.

Bayless described another incident involving a club president who was later killed in a bombing. He said he had been riding with that president, keeping his place behind him because of the man’s status, when people were allegedly waiting on an overpass for them to come through.

For whatever reason, Bayless said, they did not shoot.

Later, Sandy asked if he remembered the incident and whether he remembered a car on the side of the road. Bayless said he did not, and that realization stayed with him because it showed how unaware he had been at the time.

He told Ryan that he liked to think he had been watching everything, but in reality, he had missed things that could have killed him.

“God Was Watching Chris”

Bayless said the experience eventually left him convinced that he survived through something beyond his own skill.

“Chris wasn’t watching Chris,” Bayless told Ryan. “God was watching Chris.”

He repeated that he truly believed the hand of God was involved, especially after learning how many times people had been close to killing him without him knowing it. Bayless said there was “no doubt” in his mind that something had protected him during those years.

That part of the interview gives a personal edge to what could otherwise sound like a crime-war story. Bayless was not just listing old operations; he was looking back at a younger version of himself who was brave, useful, and committed, but also more vulnerable than he understood.

Ryan let that reflection sit inside a larger conversation about the risks of long-term undercover work, where agents may spend years living behind a false identity while moving around people who are violent, suspicious, and constantly watching for betrayal.

Bayless’ story is fascinating because it shows both the skill and the fragility of that work. An undercover agent may look like he is inside the circle, but he is also alone in ways that are hard to explain, carrying secrets that can save lives or get him killed.

The Cost Of Living Undercover

By the end of this portion of the interview, Bayless’ main lesson was not that he had been untouchable. It was almost the opposite.

He told Ryan that the experience taught him he was not “super cool Batman,” but “very foolish” and lucky not to have been killed. That honesty makes the story more credible because he is not presenting himself as invincible; he is describing how the job looked from inside the danger and how different it looked once he had distance from it.

The cases he discussed involved murders, bombings, planned retaliations, informants, surveillance, and RICO prosecutions, but the human part of the story is the lasting awareness that he was often closer to death than he knew.

Bayless said he was thankful, and that gratitude seems to come from the knowledge that many of the attempts he later learned about could have ended differently.

For Ryan’s audience, the interview offered a look at undercover law enforcement that is far removed from the polished version people often see in movies. Bayless described a world where survival sometimes depended on preparation, sometimes on luck, and sometimes, in his view, on God watching over him when he was not watching closely enough himself.