As Huddersfield boss, the Premier League giants entrusted him with teenage starlet Emile Smith Rowe.
There was, however, a strict stipulation, with Arsenal dictating the attacking midfielder was not to be overplayed.
Inevitably, such a request was not common knowledge, with Cowley admitting he earned criticism from supporters over his modest use of Smith Rowe as a consequence.
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Nonetheless, he made 19 appearances and scored twice for the Championship club after joining in January 2020 until the season’s end.
Today, the 20-year-old is a Gunners regular, featuring 33 times and scoring four goals in 2020-21.
Cowley told The News: ‘We first watched Emile play for Arsenal under-23s at Boreham Wood and followed his progress.
‘At Huddersfield, our then head of football, Dave Webb, was a family friend, which gave us a way in. We then met mum and dad, who are teachers, and got a connection there.
‘Emile had had a really disappointing time at Leipzig, who’d paid about £2m for the loan and then he’d got injured in the first couple of weeks. He was young and in Germany on his own.
‘The way Leipzig play is a very high-pressing game, extremely different to how Arsenal play. As a consequence, they broke him quite early.
‘That meant we worked really hard with Arsenal to look after him. We put in a huge amount of work to make that transition as smooth as possible – which meant we had him available to us for virtually the whole season.
‘At that time, though, Emile wasn’t able to physically play 90 minutes on the Saturday-Tuesday-Saturday, so we agreed with Arsenal that we’d manage his minutes. I would have to take him off at 60 minutes and the crowd would murder me!
‘I had no choice. Emile would be playing brilliantly in the game but we had to look after him and protect him, which was the agreement with Arsenal.
‘We needed to manage his minutes, which was the right thing to do for the boy – and, for us, it’s always player-centred.
‘When we had to beat West Brom in the second from last game of the season, we weren't allowed to start Emile!
‘You know you are going to be getting heavily criticised, but no-one really knows the full story.
‘Then he came on a sub and scored a late winner. Maybe that was the football gods looking after us!’
Smith Rowe finished the Premier League campaign with two goals in the final four matches.
Arsenal may have finished a disappointing eighth, yet the youngster represented one of the bright spots at the Emirates Stadium.
Cowley added: ‘Emile turned up for training on day one at Huddersfield and it was “My goodness”.
‘He could find space in a telephone box. When you see him for the first time, you instantly fall in love with him.’
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