During time in management at Concord Rangers, Braintree, Lincoln and Huddersfield, he has discovered a fair few rough diamonds and polished them for others to then reap the rewards.
Here, in his own words, Pompey’s head coach pinpoints his most prominent five recruitment successes...
Lyle Taylor (Concord Rangers - 2009)
Future clubs: Bournemouth, Falkirk, Sheffield United, Scunthorpe, AFC Wimbledon, Charlton, Nottingham Forest.
Cowley said: ‘Lyle had been released by Millwall as a scholar and we took him as an 18-year-old to Concord.
‘Nicky (Cowley) tells a good story about Lyle. At the time we were training at a rugby club and sometimes the council didn’t cut the grass as short as we’d like.
‘Lyle turned up late for his first session, the boys were already warming up, and he came running out, yet moved differently to players at that level. He was like a gazelle.
‘Nicky shouted to me “Sign him, sign him”, before he had even kicked a ball.
‘Lyle scored 37 goals for us that year and we sold him to Bournemouth. Eddie Howe and Jason Tindall were trying to steal him off us, we stayed strong and got a fee for him, which didn’t amount for much more than a bag of balls and kit!
‘He was the first contracted player at Concord and on £120 a week. He’ll now be on more than £30,000 a week at Forest.’
Ryan Tafazolli (Concord Rangers - 2011)
Future clubs: Mansfield, Peterborough, Hull and Wycombe
Cowley said: ‘Ryan had been released by Southampton and was an Iranian model. In the changing room, he would always do his hair before the game.
‘There was him and a boy called Jamie Butler. As a manager, especially in non-league, you want certain qualities from your centre-halves.
‘I was thinking more Terry Butcher – but I had big Ryan Tafazolli, who was plucking his eyebrows and doing his hair before games.
‘Ryan was a really powerful boy, athletic, with a good left foot. He only had a short spell with us before snapped up quite quickly by Sutton United.’
Alex Woodyard (Concord Rangers - 2014)
Future clubs: Braintree, Lincoln, Peterborough, Tranmere (loan), AFC Wimbledon.
Cowley said: ‘Alex was released by Southend and became the first Concord player to appear for England C.
‘He’s a great character, full of energy, a really combative number six, great for putting fires out and unbelievable for us. Nicky says Alex also finished his career!
‘Nicky was a significant part of our teams, right the way through to getting into Conference South. However, by that stage he’d had all of his cartilage taken out in one of his knees and it was literally bone-on-bone.
‘Nicky watched this boy in pre-season, playing in the same position as him, thinking “He’s a lot better than me!”.
‘Nicky was player-coach at that time – then became more coach and assistant manager!
‘We later took Alex to Lincoln and sold him for a significant six-figure fee to Peterborough.’
Sean Raggett (Lincoln - 2016)
Future clubs: Norwich, Lincoln (loan), Rotherham (loan), Pompey.
Cowley said: ‘We took Sean from Dover, with compensation required. We weren’t quite sure what we’d have to pay, we thought maybe £5,000-£15,000, which was a lot for a club like Lincoln at the time.
‘In those circumstances, once the player signs, it goes to an FA tribunal in a month to six weeks, so I travelled there with my chairman.
‘All of a sudden, we had to pay £50,000 – significantly more than we had anticipated!
‘I can remember travelling home by train afterwards with my Lincoln chairman Bob Dorrian. I thought he was going to cry over the money we’d ended up having to sign Sean for.
‘I told him: “Don’t worry. I promise you, we’ll make him a Football League player and we will realise that asset. There’s a bit of pain now, but long-term we will all benefit”.
‘Sean later joined Norwich in the region of £400,000-£500,000 and was brilliant for us.’
Harry Toffolo (Lincoln - 2018)
Future Club: Huddersfield.
Cowley said: ‘Harry was out of contract at Millwall and I remember the day I spoke to him.
‘I was walking around my lounge on the phone and his second sentence was “How are you going to make me better?”. I thought “I need to sign this kid!”.
‘We obviously liked his qualities from what we had seen of him. If I don’t think they are good characters then I wouldn’t sign them, it doesn't matter how good a player they are.
‘Harry had unbelievable humility, but hadn't played a game. He’d had some loan spells and lost his way, being caught up at a big club when no-one had really controlled his development.
‘He was a very young player, but was going to start every week as our left-back, so we had to upskill him very quickly to be able to cope with that.
‘When we took him to Huddersfield, it was for the best part of £500,000. I believe in January they turned down £3-4m from Premier League clubs.’
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