Having spent 14 years at Arsenal, Conor Henderson could have been forgiven for believing he was well equipped for a good career in the Football League after leaving Emirates Stadium. But the reality was quite different.
Henderson joined Arsenal as an eight-year-old and climbed his way right through the ranks to represent the first team in 2011, when he played the full 90 minutes of an FA Cup tie against Leyton Orient.
Arsene Wenger said he was “technically at the level” required to make it at the club, while Jack Wilshere described him as the “next Irish superstar”, but Henderson damaged his knee ligaments that summer and never played for the club again.
He left for Hull City in 2013, aged 21, but the midfielder struggled to adapt to football away from his boyhood club, failing to break into the Tigers’ XI, before enduring spells at Crawley Town and Grimsby Town which were only marginally more successful.
“I was nearly 22 (when I left Arsenal) and I’d only made one appearance so it was a feeling that I had to go, not wanting to go,” Henderson says.
“But for the next three or four years I found it hard to adapt to what other clubs want and they way they play.
“From eight to 21, I’d learned to play one way, and then it hit me really quick that not many other teams play this way and not many managers want to play this way.
“That was tough, dropping down the leagues and trying to adjust to that. Not having the ball for most of the game, like I was used to, doing the defensive side of things, it was difficult.”
Although he left Arsenal with only one first-team appearance to his name, Henderson, who also represented England at youth level before switching allegiances, has plenty of fond memories from his time at the club he had supported since a boy.
“I was lucky that by the time I got to training with the first team, you had Cesc (Fabregas), (Samir) Nasri, (Tomas) Rosicky, people like that,” he says.
“I was an Arsenal fan, so to be training with these guys, speaking to them and integrating with them was unbelievable.
“Cesc isn’t strong, he’s not quick, but you would never be able to get the ball off him, he never gave it away. There’s obviously a reason for that so I was looking at his awareness, his technical ability and then picking bits from that to see how I could improve.”
Having been an unused substitute in two Premier League matches, Henderson got his chance to put practice into action in March 2011 for a FA Cup replay against Leyton Orient. It’s a day he is unlikely to ever forget.
“To make my debut at the Emirates and win the game was special. I enjoyed everything about the day, and it was great to share it with my family afterwards.”
Rather than build on his first outing, though, Henderson went eight months without playing due to his knee injury and eventually felt he had no choice but to move on in search of first-team football.
Ironically, it’s only since moving abroad to join Bulgarian top division side Pirin Blagoevgrad in 2017 that the former Republic of Ireland Under-21 international is starting to feel at home again.
“I was always open to moving abroad,” he says, “but at the time I was thinking if I had a good season in League One with Crawley then maybe I could push back up to the Championship and find a team there that play football that would suit me.
“But the longer I left it the harder it got. It got to a point this summer where I had no choice (but to move abroad). I wasn’t enjoying football anymore and I felt I had to get out of the country to start enjoying it again.
“I spoke to an agent and I told him I wasn’t interested in staying in England and that I wanted to go anywhere in Europe. I just wanted to go somewhere that would suit me.
“I just wish I’d made the move sooner. It’s early days, but I’m enjoying my football more than I have been over the last few years.”
Henderson received advice from former Watford midfielder Ross Jenkins, who had taken the same path to Pirin the previous season and sang the praises of head coach Milen Radukanov. Henderson was convinced.
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“The first thing Ross said was, ‘Go for it, you’ll enjoy it, it’ll suit you.’ He had a lot of good things to say about the team and the league and how he felt it would benefit me rather than staying in England and doing what I’ve been doing for the last two or three years.
“The manager is up there with the best I’ve worked with; tactically I think he’s the best. It’s a lot more tactical over here, especially more so than League One and Two standard. Thought has been put into every session and he prepares the team really well.”
Henderson’s start of the season was hampered by an injury picked up two weeks after joining, but now fully recovered he is becoming a regular in the Pirin team. He feels certain he has made the right decision and would encourage others in a similar situation to do the same.
“If you come through a Premier League academy, especially ones at the top end where it’s drilled into you from a young age to play a certain way, it’s all about passing and moving, you’re not taught how to survive in League One and Two.
“One hundred per cent it would suit those kind of players who are taught those things to come abroad and play in European leagues.”
By Will Unwin