You probably know Damon Bennett from Holmes on Homes, the homegrown home improvement TV show that became an international success.

In 2023, Damon joined True Patriot Love’s expedition to Montana that retraced the steps of the First Special Service Force (FSSF), also known as the Devil’s Brigade – an elite group of Canadian and American commandos whose fame was secured when they took Monte La Difensa in Italy from the German army in 1943. The Montana expedition echoed the rigorous training the FSSF underwent in Montana in 1942 and brought together Veterans and civilians in a unique program of mentorship designed to support Veterans in their transition to civilian life.

Most recently, Damon took part in the second phase of the Devil’s Brigade expedition: visits to historic battlefields in Italy, including Monte La Difensa, to honour the achievements and sacrifices of the soldiers of the FSSF.

True Patriot Love had the chance to talk to Damon about the impact of the expeditions and the unexpected paths he took to join them.

Do you or your family have a connection to the Forces?

My great uncles served in the navy in World War 2, and every summer when I was growing up my grandmother would sit me down, open up the photo album and show pictures of her brothers in their uniforms and tell us stories. I’ve been fascinated about the history of World War 2 since my 20s, and right now I’m in the middle of trying to find out what ship they were on.

What motivated or inspired you to do the True Patriot Love trip to Italy?

This is going to be a long story!

When I was on Holmes on Homes, the war in Afghanistan was going on, and I had an overwhelming sense of pride while watching the news stories about people fighting.

Through the show, I had the opportunity to meet Johnny Kendall and Glen Coyle, soldiers who had returned from Afghanistan after being medically released for PTSD. They expressed to me how much they were dealing with, and as someone who also deals with depression and anxiety I could somewhat understand where they were coming from. I asked Mike if we could hire them, and he said “Yes”, that he trusted me enough to bring them on.

Through those two friends I started to meet other Veterans, and soldiers who were still serving. Johnny’s closest friends are the people he served with. I’ve since met thousands of soldiers and there’s a special bond between people who’ve served. There’s a strength with each other because of what they’ve gone through. I feel as close as a civilian can get to my friends who serve and have served, but there’s times when I know I have to step away – I try not to impose myself on the connection they have with each other.

Johnny Kendall and Jeremy Blair [Montana expedition guides] had served in Afghanistan together, it was while on tour that they came up with the idea for Off Trail Odysseys, their adventure travel guiding business. Years later, Jeremy went on an expedition with True Patriot Love and that’s where he experienced personally that people other than just soldiers also care about Veterans. It’s very hard for someone who served to get to the point where they can believe that people care about them.

So, one day Johnny texted me, “You want to go to Montana?” It was great timing; I went on the True Patriot Love expedition to Montana that was the first part of two trips following the path of the First Special Service Force. The next leg was the trip to Italy.

In Montana, I facilitated supply drops along the route, I had an SUV that we filled with jugs of water, food, medical supplies, camera equipment, and I would drive to the drop sites and unload. The only thing I was nervous about was the bears: I was by myself in grizzly country.

They would talk about the trip to Italy, but I stayed quiet. Of course I wanted to go, but I wanted to make sure others had the opportunity first. About a month before, I was having dinner with the boys and they said, “What are you bringing to Italy?” I was pretty excited at the idea of seeing where our soldiers fought and sacrificed – it’s hallowed ground.

What was your role on the trip to Italy?

I was there to help Jeremy, Johnny, and the rest of the Off Trail Odysseys team. We did the recce: we pre-climbed every hill and mountain. We pre-mounted the plaques honouring Canadian soldiers. We dropped some ropes for climbers – not me – on Monte La Difensa. Lots of people wanted to climb it so Jeremy and the boys set that up. Our friend Ryan Hawkyard, another Veteran, had a moment when he climbed it. His grandfather was in the FSSF, so to climb where he had, and stand where he stood and fought, was pretty special for him. True Patriot Love also asked me to do a social media takeover during the trip, which was fun. It was also amazing seeing the architecture in Italy because I’m a builder – people on the trip would be talking about the food and I’d be looking at the buildings surrounding where we were eating, thinking about the structure.

What impact did it have on you to be there in person?

We got to the top of Monte La Difensa, and it’s just rock and rubble everywhere, with cliffs on one side and a heavily fortified position. Where did these people hide for cover during battle? John Hart showed us the bunkers and in each bunker was a story, like here’s where a soldier jumped into a fox hole, here’s where another fought for his life, and then you start seeing the shrapnel, bullets and bombs still embedded in the earth, unexploded. It was a surreal and sad place, unimaginable to be in a place where people fought for the freedoms we enjoy, and for some who paid that ultimate price. It was heavy spot for people to stand and sit and think. I was glad I was with the right group and friends, so we could talk about it. To just absorb that was something I’ll never forget.

You’re an honorary lieutenant colonel; what does that recognition mean to you?

I was an honorary Lieutenant Colonel with 32 Service Battalion out of Downsview, ON. In the reserves, people work all day and then do their military service after work. An Honorary is a civilian role. It was the best thing I was ever a part of. To wear the uniform of your country, to me, is the greatest honour imaginable. Before my mom passed, she was able to see me in uniform and she said, “I’m so proud of you.”

How this happened is another long story!

I’ve been asked over the years to give speeches. I was asked to speak at a mess dinner at CFB Trenton. I waived my fee and did it. The colonel of the base asked if I would be interested in revitalizing the junior mess which was unoccupied and unusable. I asked, can we film it? I wanted to show Canadians what the other side of the fence looked like, and what these men and women do for our country. People are often intimidated by what’s “behind the fence” so I spent time with the different squadrons and we filmed it. The project took about a year, and we turned it into a web series called Damon Bennett On Base.

I got the call about being an honorary lieutenant colonel from John Haylock from 32 (Service Battalion) who said, “You already know half of my unit. You’re in this for the right reasons.” David Devries was the incoming CO who I ended up serving under. We really hit it off and worked very well together. David was one of the people who was part of the 2017 Invictus Games in Toronto. The Games really inspired me – it’s such a great event that honours, empowers, and gives recognition to wounded Veterans.

Canadians don’t have the American style of rah-rah-rah patriotism, but in my opinion, we love our men and women who serve, and have served, and hold them in the highest regard. As I’ve said before, one of the proudest moments of my life was putting on that uniform, and I am willing to give my time to help where and whenever I can.