During the Calgary Stampede this year, Prime Minister Justin Trudeau signed a neo-Nazi flag.

Now, Trudeau didn't know that this particular bit of cloth was part of a flag as it was tucked into the shirt of a portly Calgary man and made to look like a bandanna. The man—well-known neo-Nazi and Blood and Honour leader, Kyle McKee—waded through the crowd with a permanent marker and asked the prime minister to sign it, which Trudeau gladly obliged.

This business isn't out of the ordinary for the Canadian leader who hasn't seen a selfie he can pass up. Galavanting with crowds is normal for Trudeau—it's a major part of his brand—what wasn't normal was the flag and the man holding it.

"This is the most important the thing he's signed since he got into office," McKee says in a video of the incident posted in July. "Trudeau's signature on my nice flag."

As McKee pulls the flag out of his shirt it becomes clear, instead of being the neat and tidy bandanna tightened onto the neck of an urban cowboy this was a Reichskriegsflagge (German war flag) that was used from 1938–45.

It's no surprise when you take in mind the man who snuck it in to the Stampede. McKee is a founder of Calgary's Aryan Guard and who has, in the past, been linked to pipe bomb attacks (pleading guilty to possession of an explosive substance) and assaults against minorities. His video— recently written about by the bloggers at Anti-Racist Canada— was posted by Club 28 Canada (Calgary's Blood and Honour Chapter) and has over 30,000 views. One fan of the stunt, and the implications of it, wrote on the video's comment section that McKee was "close enough to cause some real pain ."

Tyrone Watts, a security expert and former RCMP officer specializing in VIP security services, says that Trudeau's loose security protocols, compared to other politicians, could be courting danger.

"You can't keep people away from him because he won't allow it and he wants to be up front and approachable and touched by people," said Watts. For Watts, and really, the rest of the security detail there, the real worry is that a potentially dangerous individual got in this close with the prime minister and the security weren't close enough to stop him if he wanted to try something.

"If you get in that close and he handed a pen to the prime minister, there is nothing to say that a hand movement and a knife coming out of the belt and a stab to have happened, something to bring harm to the prime minister," said Watts.

"If you look at most of the pictures with the prime minister, security isn't in tight and by the time something like that were to happen, it's too late."

Trudeau isn't the only Canadian leader that gave security headaches, this list includes the master of the ol' Shawinigan Handshake himself—Jean Chrétien, who also enjoyed wading among crowds. Famously, in 1996, the then prime minister choke-slammed a protester who got in his face, breaking one of his teeth.

Several years later, in Charlottetown, the pugilistic prime minister got a pie in his face—and the pie tosser got 30 days for assault after the incident.

This incident also shows the wide difference between Trudeau and his predecessor—Stephen Harper, a man who typically shunned activities like this. Watts, who has previously worked VIP security for prime minister Joe Clark and, at times, with prime minister Brian Mulroney, said that the security detail provided is based on the VIP's preferences, and Trudeau likes to play it "loose." However, he doesn't consider what happened "a failure." Instead, he thinks it was bound to happen with a prime minister who acts in the way Trudeau does.

"Mr. Trudeau is pretty loose with his selfies, and trying to get in with the crowd as much as he possibly can. This makes it very, very difficult for the security team to do what they've got to do," said Watts.

This isn't the first time that Trudeau's been categorized as someone difficult to provide security for. In March of 2016, Trudeau took to the slopes at Whistler and the RCMP had to put out a call about who could keep up with the former snowboard instructor.

Justin Trudeau in sea of people shortly after winning the 2015 election. Photo via Facebook.

The security for prime ministers is handled by a specific division of the RCMP called the Prime Minister Protection Detail. They're a secretive bunch but if you see a scowling man near the prime minister, you can be assured that is one of them. The team scopes out areas and provides on the location security for the VIP, among other things, but, in the end, the final boss in the PM.

Trudeau's father, Pierre Trudeau, was also a wily lil' fellow himself and would drive his security crazy—especially during canoe trips. Watts, who said he worked briefly with the elder Trudeau, explained that Justin is "following right along in his footsteps."

Watts added that saving the office of the Prime Minister from embarrassment is a part of the job if you're in the security detail saying, "I know that from days gone by that was something that was regarded as avoided as all costs." The video, entitled "trolling justin trudeau-signing Nazi flag in calgary alberta," seems to have been made specifically to embarrass the Prime Minister.

"He doesn't look at what he's doing, he just does the thing and I guess whatever shakes out afterwards shakes out and this particular case, to me, it's an embarrassment," said Watts.

"It's an embarrassment on the force, it's an embarrassment on the government, and it should be an embarrassment on Mr. Trudeau for not looking at what's he doing."