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Two charming small towns in the Ottawa Valley of Eastern Ontario. Two healthy young men growing up in the same era, both into sports, both considered normal by their friends, both ending up in uniform in the Middle East – but fighting on different sides.

When news broke early this week that Abu Anwar al-Canadi, the fighter from the Islamic State of Iraq and the Levant (ISIL) who was threatening Canadians on the Internet, was actually 23-year-old John Maguire of Kemptville, the weekly Advance was already on the stands around town.

And there, on page K15, was the story of another young man from the valley: 26-year-old Dillon Hillier of Perth. Having spent five years with the Princess Patricia's Canadian Light Infantry based in Shilo, Man., and having served one tour of duty in Afghanistan, the former soldier had paid his own way last month to Iraq, where he had joined the Kurdish Peshmerga militia and was now standing with Kurdish fighters against the very force that Mr. Maguire represents.

The irony was not lost on Randy Hillier, Dillon's father and, since 2007, the Progressive Conservative member of the Ontario provincial government for the riding of Lanark-Frontenac-Lennox and Addington. So much the same – age, background – yet so stark the contrast. Randy Hillier tried to keep the worst thoughts out of his head, that the two young men could conceivably meet in battle, but he wasn't always successful.

"It is indeed a possibility," he says.

The dramatic Islamic State video, initially posted on YouTube and subsequently played and replayed on news outlets, held a doubly chilling message for Canadians. The obvious one was praise for the fall attacks on soldiers in St-Jean-sur-Richelieu, Que., and at the National War Memorial in Ottawa that killed Patrice Vincent and Nathan Cirillo. In return for Canada joining the coalition battling against Islamic State, Abu Anwar al-Canadi warned: "Your people will be indiscriminately targeted as you indiscriminately target our people."

The other message, in some strange ways even more disturbing, was the claim that this young man dressed in mujahedeen garb was no different than any other young Canadian male.

"I was one of you," the man previously known as John Maguire says in the video. "I was a typical Canadian. I grew up on a hockey rink and spent my teenage years on stage playing guitar. I had no criminal record. I was a bright student … "

Responding in the Ottawa Citizen with a sharp slap of sarcasm, columnist Kelly Egan "apologized" to the young man: "We didn't realize hockey was so dispiriting and wrong."

Down at the North Grenville Municipal Centre – where the motto is "Today … Tomorrow … Together!" – Shaun Armitage can only shake his head at the notion that any youngster playing in the Kemptville arena could ever take such a turn. Mr. Armitage is president of the minor hockey association, overseeing a healthy local program that includes 26 boys' teams, 11 girls' teams and six beginners' groups. The values stressed by the association are all about respect, says its president.

"It's really the coaches," Mr. Armitage says. "They are the ones who pass on the values of teamwork and good sportsmanship. I'm a big believer in sports. Keep kids active, keep them on teams, keep them out of trouble."

Mr. Armitage did not live in the town when Mr. Maguire was playing his minor hockey, but queries among other long-time coaches found that he was largely unnoticed and considered a "normal" kid. While people who knew him will talk about him, they almost always request anonymity, fearful of any connection whatsoever with this disturbing story.

Friends who went to North Grenville District High School recall their pal "JMag" as bright, with a biting wit and a love of punk and hip-hop music. A joker who sometimes took things too far – earning trips to the vice-principal's office – but typical of young adolescent males. They thought him "ambitious" and likely to go places – but they never for a moment thought that might mean Syria.

His parents divorced, friends say, and John went to Ottawa to live with his grandparents and finish his education at Hillcrest High School in the capital's Alta Vista neighbourhood. But that is the last they heard of him. He simply vanished from the lives of the friends he left behind in Kemptville. He went to the University of Ottawa, travelled to California and converted to Islam. Some time after that, he adopted extremist views and bought a one-way ticket to Syria. The RCMP tracked him and the Canadian government tellingly suspended his passport.

"Everything that I hear about him now is honestly nothing like the JMag I knew," one friend told Ottawa media.

But they heard nothing from him for years, not until that video showed up and the connection was made back to Kemptville. "JMag" was now Abu Anwar al-Canadi and he had joined ISIL, the extremist group that released that grisly video of them beheading American journalist James Foley.

Dillon Hillier, on the other hand, keeps in close contact with his old pals in and around Perth. He was also sports-obsessed, although more snowboarding than hockey, and kept a wide circle of friends. "He was no couch potato, that's for sure," his father says.

At 20, Dillon joined the army, and after being discharged in March he worked for a while in the oil patch before deciding to head off and help the Kurdish fighters.

His Facebook postings to friends soon attracted some attention from the local media, something Randy Hillier tried, without success, to discourage. "It's a private matter," he argued at the time. Soon, everyone in the area knew, and the family's story could no longer be kept private.

"We are immensely proud," Mr. Hillier says. "Not many people would do what he has done. His convictions run deep. He has seen people being oppressed, not just having their freedoms taken away but living in tyranny. He decided something should be done and he's doing it."

It is really no surprise, Randy Hillier says, that someone from the area would volunteer to fight for a cause. The very first expeditionary force raised in Canada in the 1880s – nearly 400 volunteers heading off to the Nile River in the hopes of rescuing General Charles Gordon from the siege of Khartoum – was composed largely of Ottawa Valley men.

Another small town in the area, Carleton Place, lost 47 citizens in the First World War alone and produced Captain Roy Brown, the flying ace officially credited with bringing down Manfred von Richthofen, the "Red Baron."

"Beckwith Township contributed an overwhelming number of people to both wars," Randy Hillier says. "People in the military tend to come from the small towns and rural populations. I think the values that are inherent in rural Canada are to put Canada first, a desire and need for freedom."

Randy and Jane Hillier and their three other children say their pride is tempered with equal amounts of worry.

The Peshmerga forces claim that as many as 727 of their fighters have died in the battle against ISIL since the outbreak of hostilities in June, and more than 3,500 have been injured.

Several times Randy Hillier has been able to talk by telephone with Dillon. "He's trying to learn some of the language," the father says. "He tells me how impressed he is with the quality of the people he is trying to help. I tell him: 'Stay alert. Be strong. Be aware.' He's strong and he's a good man. We support him as much as we can, but there's no shortage of prayer."

As well, no shortage of wonder how one young man could go in one direction and another – once with so much in common – could go in the opposite direction.

John Maguire, Abu Anwar al-Canadi, may be the only Ottawa Valley small-towner who has gone off to join Islamic State, but he is far from the only young, male North American.

"I heard there's something like 140 of them fighting with the bad guys," Randy Hillier says. "What's going on in this country when so many are willing to join up with something that is nothing less than evil? I mean, what the hell?"

It is a question being asked far beyond the Ottawa Valley.

With an answer beyond anyone's reach.