Callum Montgomery’s arrival in Calgary may have been years in the making.

Cavalry FC’s newest Canadian defender became all too acquainted with Tommy Wheeldon Jr. and some of the current squad several years ago, from plenty of meetings in the Premier Development League between Montgomery’s Victoria Highlanders and the Calgary Foothills.

In seven appearances against Calgary across three years from 2016 to 2018, Montgomery was never able to beat them — six defeats and one draw paints a picture of the Foothills’ dominance in the PDL at that time, which perhaps serves as foreshadowing for Cavalry now being perennial playoff contenders in the CPL era.

“I remember every game [against Foothills] I was bleeding, like I took an elbow, or my eye was split,” Montgomery recalled. “There was never an easy game against them. I was like, ‘God, I just have to join these guys finally, I can’t keep getting beat up by them’.”

Now, Montgomery — a native of Nanaimo, B.C. — has joined forces with Wheeldon, not to mention the likes of Marco Carducci, Sergio Camargo, and Ali Musse, who count among the many current and former CPLers to play for the PDL champion Foothills squad in 2018.

Montgomery explained that the club culture in Calgary — their playing identity, and Wheeldon’s emphasis on hard work in particular — led him to want in. Cavalry fans will be pleased to hear that Montgomery should fit in perfectly with a team that — just like Wheeldon’s Foothills in the PDL — usually leaves a mark on its opponents in hard-fought, sometimes physical matches.

“At the base of my game I like to consider myself a bit of an old-school defender,” Montgomery said. “I love blocking a shot, saving a goal. For me, those are just as important as scoring on the other side. I still embrace that old-school style of defending.

“Growing up I was a big fan of [Giorgio] Chiellini, the passion that he had at Juventus for defending. I try to embrace that, but at the same time I think I do have the ability, I have a good left foot to break lines and find passes that can break defences down. Hopefully I can bring that together and really complete my game here.”

The 25-year-old Montgomery arrives in Alberta at perhaps the ideal time for both himself and the club. Cavalry, having lost three centre-backs this off-season — Karifa Yao, Mason Trafford, and David Norman Jr. — found themselves in dire need of a quality defender, and especially one who can play the left side as Montgomery can.

On the other side, Montgomery himself needed a change of scenery and a chance to play consistent minutes after bouncing around several clubs since leaving NCAA Div. I side UNC Charlotte. After going third overall to FC Dallas in the 2019 MLS SuperDraft, he has yet to find his footing, having spent the last few years on loan (first from Dallas, then from Minnesota United) at various USL-level teams.

Cavalry gaffer Wheeldon has had his eye on Montgomery for a while now. He told CanPL.ca that he feels Montgomery’s ceiling is well above what we’ve seen so far — and that there’s a reason he was drafted so high out of college, ahead of fellow Canadians Tajon Buchanan, Kamal Miller, and Dayne St. Clair. Now, it’s Wheeldon’s goal to help Montgomery achieve that potential.

“[Montgomery] is one who has been unfortunate,” Wheeldon said. “Whether it’s the club that he’s reported to or he’s not had that chance to play that, say, Kamal Miller has had, who was in the same draft class but he had the opportunity to play for Orlando and then transfer to Montreal. There ‘s a shortage of left-sided domestic defenders, but he would be one of the top ones.”

Weighing his options this winter, Montgomery landed on a choice to return to his home country.

“When I was looking for a new team I wanted to go somewhere and hopefully play a big part and contribute,” he said. “I was looking at the USL, CPL, but as a Canadian I wanted to come back and support Canadian soccer.

“I felt that the CPL in the moment, the league and Cavalry specifically can really help me make that jump and get back to my best. For whatever reason I never really got that chance in MLS. Whether it was injuries, coaching decisions, that sort of thing; I felt like toward the end of my time there I was at the level where I could contribute and make a difference and perform at that level, but it is what it is. When I moved on from Minnesota I wanted to find a place I could really fit in and contribute and perform at the end of the day.”

Part of what attracted Montgomery to the CPL — and Cavalry in particular — was seeing the recent track record of players moving on from the league, either into MLS or overseas. Montgomery offered Joel Waterman and Dominick Zator (both of whom had their first CPL experience at Cavalry) as examples of players who used the CPL as a springboard, and he mentioned Yao as another centre-back who developed into an MLS-ready defender at the club.

Last year also saw youngsters Aribim Pepple and Victor Loturi earn big moves overseas from Spruce Meadows.

Montgomery, who had been tapped as a possible defensive prospect for the Canadian men’s national team since his appearances with the U-23 side at the 2021 Olympic qualifiers, feels a move to Cavalry could be exactly what he needs.

By his own admission, Montgomery was skeptical of the CPL when it kicked off in 2019. Now, though, having seen the level of play and how some players have developed, he’s excited to be involved.

“Now it’s at the point where it’s very established, you’ve seen players come to the league from all over the world and clubs from all over the world are watching it as well. It’s amazing to see a league that gives young Canadians opportunities to play,” Montgomery said.

“I think this league has done so much for other Canadians, given guys chances, and you’ve really seen the league moving people on. I don’t think I want to finish my career here, I think we all want to play at the highest level we can. I felt that the CPL in the moment, the league and Cavalry specifically can really help me make that jump and get back to my best.”

Before he can think too much about the long-term future, though, Montgomery has a few dates circled on his 2023 calendar already.

Having grown up on Vancouver Island, Montgomery can’t wait for Cavalry’s first trip to play Pacific FC. He’d already chatted with fellow Islanders Josh Heard and Sean Young prior to signing in the CPL to get a feel for the league and its level, but those two Pacific players are now rivals.

He won’t have to wait long for that first away day in Langford, either. Cavalry’s second match of 2023 is a Canadian Championship tie away to Pacific on April 20 — plus, the two sides square off at Starlight Stadium again just three days later on April 23.

Montgomery will surely have plenty of friends and family from the Island watching him those two days, but his allegiance is now firmly in Calgary.

“I’m looking forward to having a great year here,” he said.

“And hopefully finally getting that North Star Shield back to Calgary.”