“You go chase your dream, go play wherever you want. I’ll keep building this here in Calgary, and you’ll come back one day and win us a trophy.”

The last trophy Charlie Trafford and Tommy Wheeldon Jr. won together was the 2009 U-18 national championship with Calgary Foothills.

At the time, a 17-year-old Trafford was about to head overseas in pursuit of a professional career in Europe, while Wheeldon was about 10 years from taking the reins of Cavalry FC in the Canadian Premier League.

On a Saturday afternoon 14 years later, sitting in the press room of York Lions Stadium, Trafford and Wheeldon found themselves within touching distance of another trophy for a Calgary club — this time, the CPL’s regular season title.

As Trafford recalled that moment from his early Foothills days, when his urged him to head abroad and pledged to establish a silverware-worthy professional club at home, Wheeldon gestured at the actual goosebumps forming on his arms. Trafford had, indeed, carved out a career for himself overseas, playing nine years across four countries before signing for his hometown club in 2022.

Cavalry were somewhere over the Prairies when they first started celebrating their CPL Shield triumph on Saturday night, disturbing the peace of an otherwise ordinary commercial flight from Toronto to Calgary. Forge FC’s win over Pacific FC in Hamilton meant the Cavs — seven points clear of the field with two matches to go — officially clinched what will be the first proper silverware in the club’s history.

Since day one of the CPL, Cavalry have been a club built on winning. No CPL side has won as many league matches as they have, with 65. In 2019, they steamrolled their way to both the Spring and Fall season titles, but were not recognized for it with a trophy or a continental competition — instead, they watched Forge FC first compete in the Concacaf League and then lift the North Star Shield in front of Cavalry’s fans at ATCO Field.

In 2021, Cavalry finished the year with as many points as Forge, but again went empty-handed into the off-season after a semifinal loss (again at home) to Pacific. Again in 2022, nothing — their season ended in Hamilton with another semifinal defeat.

Only two players from that dominant 2019 team remain in the Cavalry squad today: Marco Carducci, the club’s captain this year; and Sergio Camargo, the club’s first-ever player (simultaneous with Nik Ledgerwood, who remains a Cav as part of Wheeldon’s coaching staff). In a bout of intense poetic irony, it was Carducci’s four-save clean sheet and Camargo’s winning goal that led Cavalry past York United on Saturday, with one last favour from their old nemeses Forge officially sealing the title later that evening.

At last, Cavalry have a tangible prize to speak of, and when they lift the CPL Shield on Oct. 7 in front of their own fans in Calgary it might feel more like the culmination of five years’ work than just one.

In a hotel in Vaughan, Ontario on Friday night, the Cavalry players remained fully focused on the immediate task at hand the following day at York. Palpable, though, was the sense that they knew what the next day might hold. To neutral observers, clinching the title would be almost a formality by that point with the Cavs having two home games left after their visit to Toronto.

Within the squad, though, was a clear hunger to get the job done as soon as possible.

That night, Ben Fisk told a story about the last time he won silverware. He was a member of the 2018 Derry City side that triumphed in the League of Ireland Cup, with Fisk starting at left wing in a 3-1 win over Cobh Ramblers.

A few days before that final, Fisk says some of his veteran teammates brought the younger players out for a nerve-calming pint.

“They just started listing off well-known players,” Fisk recalled. “They said, ‘These guys have all made millions in their career, played at the highest level, but do you know what they all have in common? They’ve never won a f—ing trophy.’

“That to me kind of put it in perspective. Harry Kane, one of the best players in the world, just made a big move, with the main reason — what is it? To win trophies. Regardless of the level you’re playing at, regardless of the country you’re playing in, it’s pretty special and something never to take for granted.”

There’s very little risk of Cavalry taking it for granted when they’re presented with their hard-earned silverware.

Year five of Cavalry Football Club hasn’t always been a smooth one, and by no means have they looked like champions-in-waiting at every moment. In preseason, they lost to a university team in the Portland Pilots. They started the season with five consecutive draws — six if you count one in the Canadian Championship, which saw them knocked out on penalties by Pacific. In that stretch, they’d taken the lead seven times and coughed up every single one of them.

During the campaign, the club said a teary-eyed goodbye to a cult hero in José Escalante. Jordan Santiago, Cavalry’s goalkeeping coach since the first season, stepped away in July and Jake Davis arrived to fill his shoes, and Carducci didn’t miss a beat between the posts. In June, they had to bid farewell to a key attacking threat in Mikaël Cantave in order to bring in a more unknown quantity in U-21 winger Maël Henry from Vancouver FC.

“There’s no success without suffering, and I think we went through that,” Wheeldon said on the CPL Newsroom on Monday. “The biggest challenge was the six ties in a row; we hadn’t tasted victory for six games. We hadn’t really lost, we knew we were onto something.”

For a moment, things could have gone off the rails in Calgary. They kept dropping points, and it’s in times like that where self-doubt begins to creep in. Outside of the club, some questioned whether Wheeldon’s style of play was going to work. In the locker room, pressure mounted on the players as well as their coach.

“We’ve had moments in the season where maybe [Wheeldon] could have had less faith in us,” admitted Cavalry fullback Bradley Kamdem. “But throughout the season even in the difficult moments he’s always had faith in us, he’s always been by our side.”

Things turned around for Cavalry before long. They beat Atlético Ottawa 2-0 at home on May 21, and all of a sudden their winless streak was an unbeaten streak. Since then, they’ve won another 13 games, losing just five times, and only once on the familiar grass of Spruce Meadows.

The front-footed system Wheeldon established in preseason began to click, and the squad found itself bolstered not just by the arrival of Henry but also that of William Akio — scorer of five goals in his first seven games — and Tom Field, returning to the pitch professionally for the first time since 2021.

If Cavalry have always been, at least, one of the top sides in the CPL but have never quite cleared the hurdle that would give them a trophy, something must be different about the current side.

“It’s the intangibles,” Camargo suggested.

“It’s the things you don’t see. It’s the conversations that are being had every day in the locker room between coaching staff and players, and between players. There’s just constant dialogue this year that I don’t think has been there in years prior, and that has allowed us to build trust, to build togetherness, and just to build to one common goal which is a championship.”

One championship has now been secured, and at the end of this 28-game marathon Cavalry will be justly rewarded for crossing the finish line ahead of the pack. They’ll lift the Shield at home, and then hope to play there again twice in the playoffs — which could set them up to be the first CPL side ever to win a double. In the new year, they’ll set foot in pastures new in the Concacaf Champions Cup.

When Carducci, Camargo, Wheeldon, and all the others who remain from Cavalry’s inaugural season finally do get their hands on that trophy, they’ll be thinking of more than just the 28 games that preceded it. They, and the legions of Foot Soldiers who came along for the same ride, will remember heartbreak, and falling at the final hurdle.

They’ll remember those days in 2019, on the bumpy horse-trodden original pitch under a single floodlight at Spruce Meadows, where this moment might not have felt five years away.

All that is now history; the early chapters of a Calgary soccer story that had its prologue in that 2009 conversation between Wheeldon and Trafford.

They were the first team to win a CPL regular season in 2019. Now, Cavalry Football Club will be first to lift a trophy for it.