Charlie Lennon has explained that his decision to leave Middlesbrough was driven by a desire to test himself in men’s football, with the timing finally feeling right to move on after a decade at the club.
The 19-year-old winger completed a permanent switch from Middlesbrough to Barnsley on Saturday, signing a three-and-a-half-year contract with the option of a further year, bringing an end to a journey that began at under-nine level in Teesside.
For Lennon, the move was less about walking away from Middlesbrough and more about stepping towards the next phase of his development. Having made his senior debut for Boro in April 2024, opportunities at first-team level remained limited, and a loan spell earlier this season proved decisive in shaping his thinking.
“I loved my time at Middlesbrough,” Lennon told Teesside Live. “I had great experiences there, playing against top academies like Chelsea and Manchester City. But it was probably time for me to move on from that this season, and that’s why I went out on loan.”
That loan came with Darlington in the National League North, Lennon’s first sustained taste of men’s football. Operating in a more physical environment and across different positions, he contributed two goals and seven assists, form that did not go unnoticed further up the pyramid.
“Darlington was my first time away from Middlesbrough and I really enjoyed it,” he added. “It was my first time in men’s football, playing different positions and learning a lot. It did me the world of good.”
With just six months remaining on his Middlesbrough contract, Barnsley moved quickly to secure his signature. Lennon admitted the clarity of the opportunity made the decision straightforward once interest became concrete.
“I’m delighted to be here,” he said. “As soon as I heard there was interest, I wanted it to be sorted. Barnsley play young players, and the way they play really interested me. I just wanted to get it done as soon as I could.”
He also pointed to Barnsley’s track record of trusting young players as a major factor in his choice, something he believes will ease his transition into League One football.
“The record shows the club trusts young players to do a job,” Lennon explained. “I’m 19, so it’s great knowing I’m coming into a side with lads around me in a similar situation.”
Natural progress
From Middlesbrough’s perspective, the move represents a natural part of academy progression. Academies aren’t purely there to create footballers for their clubs; they’re there to produce footballers, and if that means players who are sold for profit, so be it. Lennon leaves having progressed through every level of the club’s youth system, earned England youth caps, and made his senior debut, before moving on in search of regular first-team football.
Barnsley, meanwhile, view Lennon as a player with significant long-term potential, but one who is ready to compete immediately. He is expected to go straight into contention for first-team minutes under Conor Hourihane, marking the start of a new chapter that Lennon feels is perfectly timed.