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Almost 70 years ago, my grandfather, Jack Starr, opened the doors of The Horseshoe Tavern. My childhood memories include a banquet burger with Stompin' Tom Connors, and Sunday mornings when I would help "Papa Jack" count a safe full of one-dollar bills…

Fast forward to last night and the annual Skydiggers' Christmas show, where a band I literally grew up with delivered their extensive songbook with such effortless joy that the love between band and fans became increasingly palpable with every sweet harmony, keyboard run, guitar lick and rock-steady beat. The "Skydiggers choir," as Andy referred to the audience, singing every lyric to every song, was in fine form.

When I say "literally grew up with," I really mean it. The lead singer, Andy Maize, lived two doors down, was in my sister Paula's grade at school and delivered our Globe and Mail (standing in our front hall to collect while our dog, Auggie, has his way with him – bad dog). The guitarist, Josh Finlayson, and I have been close friends since kindergarten, so Christmas at the 'Shoe is a real homecoming for me.

But last night was special. On so many levels and for so many reasons. Tom Wilson and his son Thompson (billed as Tom Thompson) opened the night, their confident voices demanding the attention of the festive crowd. Tom talked and sang about his troubled past, of a Christmas spent in a Hamilton jail cell, and another in rehab away from his family… But standing on that stage and singing with his son, there was only forgiveness, redemption, gratitude and love. "Look after each other," he said. "Go into the world and love everyone."

I was watching from the "office." It's where owners Jeff Cohen, Craig Laskey and their team have created, curated, nurtured, lived and breathed the Toronto music scene for more than 25 years. A big set of wooden shutters are built into the wall and they swing open for a perfect view of the stage.

I was catching up with J.C. before the Diggers went on when Gord Downie, Kevin Hearn and some of their friends made their way in quietly through a back door. The Hip and the Skydiggers came up together. And Josh has been involved in a number of Gord's projects, including playing guitar in the Secret Path band.

Trying to play it cool (good luck), I waited for my chance to say hello to Gord and to thank him for shining a light onto First Nations issues. I explained that about a year or so ago I had started to research the real history of this country and that I was committed to doing something about it. And I am. He smiled and gave me a low-five – half-slap, half-handshake. We talked a bit about Secret Path and the recent ceremony where he was honoured. He said he couldn't really describe the feeling of that moment.

Shortly after 11 p.m., the Skydiggers took to the stage. About three tunes in, Gord's brother, Mike, appeared with a small group. I quickly realized it included National Chief Perry Bellegarde and his partner, Valerie. I stepped away from the windows and motioned for them all to step up for a better view.

I soon found myself next to Chief Bellegarde and asked him if he had ever been to the Horseshoe before. "First time," he said with a warm grin. He and Valerie were smiling, standing close together, watching the performance, watching the crowd sharing and singing, Andy dancing, pulling and tapping invisible levers of rhythm and backbeat, like a transcendent conductor whose hands command a world of unseen waves.

I spoke briefly with Chief Bellegrade about the Horseshoe, about my friends in the band, and about what I have learned over the past 18 months. I was probably too earnest. Too eager to show that I get it. But he genuinely appreciated what I had to say and we agreed that everyone in this country has an obligation and responsibility for our past, and for our future. I told him that I want to help and he gave me his card and asked me to e-mail him. I did that this morning, before I started on this.

Soon the band was into I Will Give You Everything and then A Penny More.

"Higher, higher/You take me where I want to go/Higher, higher/You take me where I want to go"

I noticed that Gord had stepped back away from the group. He was alone on the back wall, slightly out of sight at the start of a narrow corridor. Was it the poet stepping back to observe and capture the moment, or was I just seeing him metaphorically slipping away…?

It was time for the first encore. Slow Burning Fire with Pete Cash and Andy singing it together just as they had more than 20 years ago on this same stage. When the song hit its stride, everyone was dancing – the hundreds of people in the venue and the dozen of us in the office. Andy's wife, Andrea, pulled Gord in and they were dancing between the desks. It was the Twist meets the Pony, a super-slow-motion robot as only Gord could do it with Andrea ethereal as ever, and all smiles. Everywhere, everyone smiling, everyone singing, everyone happy and full of life.

Andy was talking now. Thanking the patrons, his bandmates, the crew. The crowd was cheering and clapping. They knew there was still one song to be played….

"Good King Wenceslas looked out/On the feast of Stephen/When the snow lay round about/Deep and crisp and even/Brightly shone the moon that night/Though the frost was cruel/When a poor man came in sight/Gath'ring winter fuel...

"Sire, the night is darker now/And the wind blows stronger/Fails my heart, I know not how/I can go no longer.

"Mark my footsteps, my good page/Tread thou in them boldly/Thou shalt find the winter's rage/Freeze thy blood less coldly.

"In his master's steps he trod/Where the snow lay dinted/ Heat was in the very sod/Which the Saint had printed/Therefore, Christian men, be sure/Wealth or rank possessing/Ye who now will bless the poor/Shall yourselves find blessing."

I sat down next to J.C. who was still working away amidst the party. I asked him what he thought my grandfather might say if he were to look down on the evening. He paused and smiled. "Just another night at the 'Shoe."

Gary Clairman lives in Guelph, Ont. His website thetreatypeople.ca will launch in early 2017. You can find him on Twitter @GaryClairman

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