The 27-year-old, who has been capped 14 times by the Wallabies and played at the 2019 Rugby World Cup, is stepping out of his comfort zone with his switch to the northern hemisphere.
His path to Glasgow has been smoothed by relatives who live in the city – an important factor in his decision to relocate. His tartan ancestry is on his mother’s side, through his late grandfather, Andrew Prentice.
“He was born and raised in Glasgow and I was taken out by my cousins to where he grew up during my first weekend here,” Dempsey explained. “He met my grandmother who was Australian and they moved to Australia together.
“He passed on when I was 12 so I have a lot of memories of him. They moved from Glasgow to western Sydney, so out in the sticks. They bought this little shed in the country and my grandad built the house my mum was brought up in. He had this really thick Glaswegian accent. I was lucky to have that in my life and now I’m meeting his whole family over here. It’s good to have that connection.
“You always have that heritage and ties to a country and to a city and that means a lot.”
The decision to leave Australia was not one Dempsey took lightly but after seven years with the Waratahs, he felt it was time for a change.
“There were a lot of reasons but the main one would be from an individual point of view as a rugby player I was feeling I had plateaued over the last couple of years back home with my club side.
“I was lucky enough to play in the World Cup but coming out of that I didn’t think I was growing as much as I could and should.
“Without going into the technical and tactical reasons for that, it made me want to get more experiences. Once I made that decision I looked at clubs and when the opportunity to come to Glasgow arose it ticked the boxes I wanted. It felt like the right fit.”
Primarily a No 8, Dempsey says he is comfortable playing across the back row which is likely to be an area of strength for Glasgow in the new season as he vies for selection with the likes of Matt Fagerson, Ryan Wilson, Rory Darge, Rob Harley and Ally Miller.
He won his last caps in the pool stage fixtures against Uruguay and Georgia at the World Cup and, with the Wallabies reluctant to select players from outside of Australia, the forward knows that the move to Glasgow is likely to signal the end of his international career - for the foreseeable future at least.
“That’s what I had to weigh up, and it was a sacrifice I had to make in order to do this.
“It’s about being healthy and being in form as to whether or not you get the chance to play Test footie, but for me all that was secondary to the fact that I wanted to improve as a rugby player, and the stuff that I wanted to improve I didn’t know if I was going to get that staying where I was.
“I’m only 27 now and I feel like I’ve got heaps of footie in front of me, so you never know what is going to come round the corner next.
“But it wasn’t an overnight decision to come here. I definitely weighed everything up, including the national programme back home, so it is not something I took lightly. I definitely know what I am walking into here and I have no regrets with that.”