The 63-year-old Halifax man has cerebral palsy. He's proudly cheered on his team ever since he became a fan 48 years ago, when the team last won the Stanley Cup.
Now, his longtime wish to see a game is about to become a reality thanks to a mysterious donor to Northwood, the continuing care facility he's called home since 2005.
"I shared with him the dream that Bobby wanted someday. It was on his bucket list before he passed away. And he just said, 'Make it happen,'" said Faye LeBlanc, the managing director of Northwood Foundation.
The donor is paying for the airfare and hotel for Desmond, two nurses and an occupational therapist to see the Leafs take on the Ottawa Senators on Easter Sunday. Rogers Communications Inc. is covering tickets for the game.
Northwood staff are working on last minute details such as securing travel documents for Desmond.
"So excited, so excited," he said with a broad smile.
Janet Egli, the nursing manager on Desmond's floor, is joining him on his dream trip.
"Bobby's basically a legend here at Northwood and everybody knows just his great love for the Toronto Maple Leafs team. The fact that I get to be a part of that and to be able to experience it with him is just beyond words," she said.
Desmond's room is covered in Leafs swag. A glass case with Leafs memorabilia, including a goalie mask and a jersey, takes centre stage across from his bed.
Banners, flags and towels all bearing the Leafs logo cover his bedroom and bathroom walls. Even his tissue box and waste paper basket have the Leafs symbol.
That fierce devotion to a team has won him fans among the 850 residents at Northwood.
They're cheering on Desmond as he gets ready for his big adventure in Toronto, which includes a side trip to the Hockey Hall of Fame.
"I think it's wonderful. Couldn't happen to a nicer guy," said Irene Gray, who also cheers for Toronto.
Even Habs fan Bob Enos is happy for him. "It's cool. It's nice to see someone you know get something he really wants. Doesn't happen often enough."
Desmond, who considers himself the team's number one fan, is thrilled his team beat the Senators in overtime 4-3 last Saturday. He's hoping the team bests the Sens again this Sunday when he's there under the same roof to root for his Leafs.
"I want you guys to go, go, go," he said pumping his fists.