- by Joe Baker
At the age of 16, he had the huge decision of whether to choose rugby or football, and with the pressure of his Dad being a former rugby league star he was expected to sign for Wigan Warriors, where he had earned a scholarship.
It took the youngster a long six months to make up his mind, but what ultimately swayed it, was that he was a local Cumbrian.
"It took me a good six months to decide. It was Christmas time when I was offered my youth contract [by United], and I had to decide whether to sign it then. So I had to tell Wigan, 'Listen, thanks for the support, but its Carlisle where I'm going'.
"Basically, it came down to being local, and being a Carlisle supporter since I was young."
A shining light in a struggling Carlisle team, and after a particularly impressive performance against Derby in the Capital One Cup, Dempsey has attracted interest from Premier League club Burnley. Manager Keith Curle has attempted to reassure fans that he is not for sale.
"Burnley have been linked with the teenage midfielder. I spoke to Sean Dyche last week about Tom Anderson and I'm sure if there was any interest in any of our players he'd have mentioned it then," said Curle to talkSPORT.
"I've had no conversations or approach so we can put that one down to rumor-mongering."
Such is the temptation that it is for players like Dempsey to jump ship, Curle has spoken of the importance that money is not everything. If he were to enter the dizzy heights of the Premier League, it would not be guaranteed Dempsey would feature, let alone make the starting XI. What would be likely is that he would be sent out on loan - perhaps to Carlisle.
Certainly, this may not necessarily have its downsides, however being sent out on loan season after season does not do every player good.
It may be wise for Dempsey to continue plying his trade in League 2, before signing for a club like Derby County, who are looking very likely to return to the top division, and are renowned for producing youngsters and playing them in the first team.
This was echoed by United manager Curle: "I've told Kyle that if he wants a move to a Premier League club, I'll phone up Neil Warnock (of Crystal Palace) and get him to come and buy him for a nominal fee. He will go into their Under-21s and then not be seen for three years. How is that progression? He can stay here and play 50, 75 or 100 games then play in the Championship and get a transfer into the Premier League."
If Dempsey can continue to keep his head down, and turn in man of the match performances, eventually his time will come, and he will get the chance to test himself against the very best.