I'm listening to Montreal Center 133.97 where the controller is switching his flights from say the Rouyn sector to the Timmins sector and asking the pilots to keep trying every XX minutes or XX miles and 'if no joy (if no communication)" keep trying. My question is if the controlle knows there will be no joy prior to handing off, why hand off in the first place?
Because the aircraft is about to leave the first controller's airspace.
Based on my piloting experience, when a handoff occurs in the US airspace, the controller first coordinates the handoff with the adjacent sector using a land line or some other off-radio method of communication. After the adjacent sector's controller accepts the handoff, the first controller then directs the aircraft to contact that new sector on a specific frequency.
In your scenario, the aircraft was most likely accepted by the bordering sector and it was about to pass through a known area of temporary radio-free airspace.
The IFR system is designed to handle momentary or complete communication failures between ATC and IFR aircraft.
As a sidebar: In the US, the phrase "no joy" is used by ex-military pilots to indicate that they have not spotted traffic called out by ATC. "Tally Ho" is its counterpart, meaning "traffic in sight." I have never read of this dual meaning before your post.