The 24-year-old required a knee reconstruction after tearing his anterior cruciate ligament in round four last year and missed the rest of the season. But he has his eye firmly set on playing a part in the Bombers' pre-season campaign.
""It's obviously up to the coaches and fitness staff and if they think I should be right, but I'm hoping to play,"" Dempsey told essendonfc.com.au.
""I'm putting my hand up to play, but as I said, it all boils down to the coaches. The knee itself is progressing well.""
Dempsey rejoined full training at the club in early February, and has enjoyed a relatively smooth path back to fitness.
Only a calf strain at the beginning of pre-season when his body hadn't yet become accustomed to training loads has interrupted his progress.
""It was a bit frustrating and annoying because it put me out for a good month,"" he says. ""It was just about getting back into it full on and my legs weren't used to it at that stage.""
Dempsey's approach to injuries has changed over time. The first three years of his career were ravaged by hamstring, leg and back injuries, giving him a wider perspective on how to handle setbacks.
This time, though frustrated, Dempsey knew how to take the challenge in his stride.
""After the first three years when I was rattled with the hamstring injuries, I was always down and out,"" he says. ""Being so young, I wasn't used to missing games of footy and it was pretty hard.
""Now that I've matured I just take it as part of the job. But it's still hard, because that is my job: I have to be out there playing footy.""
Having teammate Jason Winderlich beside him through the rehabilitation process was beneficial.
Winderlich also underwent a reconstruction after injuring his knee in round four, and has provided a reference point to Dempsey as they went through the rehab group together.
""They were similar injuries but were also totally different as well. He had a bit more done to him than what I had,"" Dempsey said.
""But it was good to have someone there to know that we're both going through the same issues.
""We're just itching to getting out there and playing footy because we're sick of sitting around watching it. ""
Importantly, Dempsey hasn't wasted his time away from the game.
He did take a trip home to Cairns through last year to spend some down time with his family, but also used the extra time to pass on some advice to teammates who had filled his spot at half-back, occasionally going to the rooms and giving tips on how to beat opponents or when to attack.
But he was also learning himself. He took more time to study the game plan, particularly defensive zones and where he should be standing at different points of games. ""It's practically like sitting in a classroom and being back at school,"" he says.
When he does return, Dempsey will cut a different figure. He's added four kilograms to his frame to help reduce being buffeted off the ball, and has not shaved for months, leaving a very thick, long beard.