It is 11 years since Bailey was told he was not good enough to be kept on by Fulham, leaving him to discuss his next step with his parents in Hammersmith .
For years it looked like the teenage forward would be unable to fulfil his dream of becoming a professional footballer.
After leaving school, he spent time as a lifeguard at the local leisure centre as well as working on his father's stall at North End Road market, in Fulham.
But having impressed during his non-league stint with Sutton United before helping Barnet back into the Football League in 2005, Bailey's goalscoring talent from midfield has led to a gradual rise to prominence, ultimately catching Strachan's eye.
If you stick to it, you believe in yourself and you are prepared to work hard then it s h o w s through. I did those things and I have got back up to the top level,
said Bailey.
It's hard when you are rejected. You have to go out and find jobs and things like that. I have done a variety of jobs in my time ,playing part-time football. I used to work as a lifeguard, gym instructor, in a bookmakers, hoping someone would come in for me and sign me.
I also helped my dad down the market, unloading his lorry. It was hard work but it was something I had to do. I had my football to look forward to later in the week once I finished work. It was the only way I could get my money.
Impressing as a teenager under Paul Fairclough at Barnet led to Southend United paying £175,000 for him in 2007 and, after failing to sign a new contract, he was sold to Charlton a year later for £750,000.
Two seasons later, on the back of scoring 25 times and finishing top scorer in each of his campaigns at the Valley, he has moved to Middlesbrough for £1.4m, confident of leading the charge to the topflight.
It's a massive move for me, he said.
My aim is to play as high as I can and this will help me to do that. I have been here before, there's a lovely hotel, golf course and e v e r y t h i n g about it is top quality. It's a massive club and everything is designed here for the P r e m i e r League.
Every little boy who likes f o o t b a l l ' s dream is to play in the Premier League and mine is no different.
I have come here to Middlesbrough to show what I can do and hopefully it is good enough to lead us in that direction.
As Bailey sat in his chair at Boro's Rockliffe Park training headquarters yesterday recalling his route to Teesside, Strachan's smile was one of satisfaction.
Without kicking a ball in a red shirt, Bailey's determination to succeed and return to the upper echelons of professional football is borne out of a character which Strachan wants all of his players to possess.
You can usually determine someone's character on a football field, said Strachan, who first tried to sign Bailey in January. People can talk a good game but when they go on a football field that's not always the case.
You have to do your background work on a player.
What's he like Does he mingle with players Is he a good person We do all of those things. We have to do that more, it's like due diligence.
Bailey has heard a lot about his new manager and claims he's not looking to be on the wrong end of his wit.
As a keen golfer, the 26-yearold is keen to hit the Rockliffe Park course, although ninehandicapper Strachan quipped I might send him and the rest of the players on a run around it.
Official confirmation of Bailey's signature arrived just two days after Kris Boyd was paraded in front of the media following his switch from Rangers.
Now Strachan intends to get a £1.5m, rising to £2m, deal done for Celtic's Stephen Mc- Manus in time for the defender to make the trip to Ireland, where they play the first of two matches against Athlone Town on July 19.
Strachan, aware that Blackpool and Leeds are now interested in Gary Hooper, said: Two main targets done. I would be hoping for more within the next ten days.
Strachan also insisted there has been no contact from either Leeds or Bristol City for striker Leroy Lita, although there has been snippets of enquiries for some players.
Source: Northern Echo
Source: Northern Echo