The first time I saw him was in a Fitzgibbon Cup game for Waterford IT. I was hoping he was a young lad from Galway that I didn't know but that thought didn't last long. Someone told me he was from Kilkenny and I thought to myself 'Here we go again.'
The last time I saw him was on a night for Ballyhale recently. The players were getting their All-Ireland medals but Henry was getting a special presentation in recognition of winning his tenth Celtic Cross with Kilkenny.
They presented him with a watch and we joked that it was either a hint to tell him it was time to go, or to be on time for training.
The time was right. It is fitting that he departs the stage a champion for both club and county. People can hang on for various reasons and sometimes the wrong reasons. As with most things, Henry got this just right. He couldn't have picked a more apt opportunity.
He leaves an indelible footprint but one that didn't always seem likely. He wasn't the prodigy that say DJ or Charlie Carter were but he moulded himself into something special.
The debate on where he stands in the all-time list of greats will never be settled. Comparing eras is difficult and sometimes pointless.
But I can say that when he was at his peak he was the best. He'd deserve his place on any team you'd care to dream up.
Yesterday he picked the 2012 All-Ireland final as his high point. I'd have to agree. Not only did he take the game by the scruff of the neck, Galway seemed to be stifled by him too. Rarely has force of will been combined so deftly with skill.
His incredible medal haul ensures he stands out on his own in GAA history. He was front and centre for all those successes.
But there was more than just sport to Henry. From early in his career he was more than just another hurler.
He gave freely of his time. He never turned anyone away when reams of children would clamour around his knees for a signature or photograph.
He was part of a team that ruled hurling with an uncompromising authority and that, at various times, people across the country wanted to see beaten. Henry was the figurehead of that side but he could go anywhere and be recognised and respected.
Still, he remained modest. You'd never have known he was a man who won all those medals and accolades.
And maybe that's what made Kilkenny so hard to beat. They were all level-headed lads who'd enjoy their successes before knuckling down again.
In that regard, he's make a tremendous ambassador for the GAA at their various functions. He'd be the ideal face for Croke Park.
Down the line, he seems to have all the credentials to be a future manager of Kilkenny. But you suspect first he'll take time to reflect and spend time with his young family and give whatever he has left to Ballyhale. Shefflin's future is a discussion for another day.
In the short term, Kilkenny will, of course, go on without him. In fact, the Cats had already started to move on last season. In the same way that Shefflin took over the frees from Carey, TJ Reid was the man handed the responsibility last year.
In Richie Hogan, they have the current Hurler of the Year. Colin Fennelly will get better and he could be anything. The King has abdicated but the succession has already begun and Kilkenny will be a ruthless and as relentless as ever.
You sense Shefflin wouldn't have it any other way. Time moves on, and regardless of how big the individual may be, the team always comes first.
Perhaps that is his greatest legacy.