It started with a mother catching sight of a newspaper item on her way home from work and thinking that sounded just right for her boy, a Chelsea fanatic: his favourite club were offering a contract to the winner of a reality TV show. Had they known that 12,000 other wannabes had the same idea, they might have been deterred. But the 16-year-old Sam Hurrell was up for a shot at Football Icon, billed with typical Sky understatement as "the most ambitious TV talent show ever launched... to find a player good enough for the Premier League champions, and this man – Jose Mourinho".

Several months later, to his own astonishment, Hurrell was declared the winner and became a member of Chelsea's academy, working under a highly regarded coach named Brendan Rodgers at the sumptuous Cobham training centre.

Whether the story has a happy ending depends on your understanding of happiness. By last May, as his contemporary and rival left-sided midfielder Ryan Bertrand was selected for the Champions' League final in Munich, Hurrell was watching the match on television in New Orleans during a stint playing for the local Jesters club, two levels below Major League Soccer.

Last Tuesday, at 24 – an even younger age than Mourinho and Rodgers began – he took a first step into management. Appointed as co-manager of Hillingdon Borough in the Spartan South Midlands League, he was forced to play himself against Oxhey Jets despite a hip injury, one of half-a-dozen newcomers who had not played together before, because most of the team had walked out with the previous manager. The regular goalkeeper having defected on the morning of the match, the chairman's son went between the posts. And at half-time Hillingdon were losing 5-0.

He laughs about it now, not least because the final damage was no worse than 6-2. He laughs a lot, an easy-going young man in a Chelsea top who is "not one to get carried away with anything". It was difficult not to, however, in those heady days at the climax of Football Icon.

"I got into the six-week trial with the 12 finalists and then an X Factor -type elimination every week," he recalls. "The final three of us travelled to South Korea and Holland, then the decision was made. Jose came over for the last game.

"Once I'd won it I spent quite a few sessions training with the first team, which was a bit nerve-racking. I remember Joe Cole coming over and saying, 'Hi, my name's Joe'. I was like, 'You don't really need to introduce yourself, I know who you are'."

The original prize was a six-month contract, and Hurrell did well enough to earn a 12-month extension. But having Bertrand and Scott Sinclair as competition hardly helped him, and after 18 months he was released.

What the TV programme never quite owned up to was that as only 16-year-olds not associated with professional clubs were eligible, the chances of finding a genuine undiscovered jewel were slim. By that age, many boys have been training at a big club for eight years.

"Maybe starting at an earlier age I could have done it," Hurrell says. "But until then I had just been coached by people's dads. In the 18 months I had there the development I made was unbelievable. I think I gave it everything. I used to stay late to do extra work, because I knew I was playing catch-up."

After leaving Chelsea he had trials with Rangers and Aberdeen, but both wanted someone ready to play in the Champions' League. "A lot of [English] clubs looked at me as someone who'd just won a TV competition and didn't give me a chance."

A couple of summers in New Orleans proved more enjoyable than his experiences in non-League football, which chimed with those of his co-manager at Hillingdon, James O'Connor. He was released by Bournemouth at 19 and at a lower level found "I hated it in non-League. Got told off for passing the ball." Hillingdon will follow the Rodgers philosophy that the ball does not get tired, so keep passing it.

Hurrell now takes three coaching sessions with youngsters at Chelsea each week, hoping to find players to go a step further than he did. "Obviously Ryan Bertrand is one, Josh McEachran seemed to get some game-time under Carlo Ancelotti, but with the demands and pressure on the manager of the first team it's hard to blood the youngsters because he's expected to challenge for everything. I can see it from both ends."

Yesterday he took a session at Cobham in the morning, then headed for AFC Dunstable while Bertrand and the rest were turning out at the Emirates against Arsenal. "I'm quite a realistic person. I look at it that I could have done more in the pro game but probably not to Chelsea standard. Ideally I'd like to do some coaching full-time in the future. But you've got to start somewhere."

Where are they now? Chelsea Under-18s 2006-07

James Russell; Boreham Wood

Nick Haman; Carshalton

Carl Magnay*; Gateshead

Harry Worley; Oxford United

Ryan Bertrand; Chelsea

Sam Hutchinson; Nottingham Forest (on loan from Chelsea)

Sam Hurrell; co-manager, Hillingdon Borough

Jack Cork; Southampton

Shaun Cummings; Reading

Dean Furman; Oldham Athletic

Tom Taiwo; Hibernian

Jimmy Younghusband; Philippine Azkals

Tomi Saarelma; SR Delemont (Switzerland)

Frank Nouble; Wolverhampton

Scott Sinclair; Manchester City

*winner of second Football Icon, 2006