Luke Ayling joked that Thierry Henry single-handedly ended his Arsenal career while admitting he was left "hurt" following his emotional Leeds United exit.
The 33-year-old progressed through the academy of the north London club and remained there for a decade. In July 2009, Ayling penned his maiden professional contract after his standout performances in Arsenal's double-winning youth squad during the 2008/09 campaign.
At just 16, he received a harsh introduction to senior football when tasked with marking the legendary Henry during a training session. Reflecting on the daunting challenge he faced, he revealed to Joe Wilkinson on the My Mate's A Footballer podcast: "I trained with Henry.
"The first training session, I was about 16. He absolutely destroyed me in that first training session. It took me about two years to go back over there to train [with the first team]. Because he'd done me that much."
Despite his successes within the youth setup, Ayling featured in just one first-team matchday squad for Arsenal and departed the club in 2010 without earning a senior appearance.
He joined Yeovil Town that summer, bringing his decade-long stint with the Gunners to a close, and jokingly referenced Henry's impact on his departure by saying: "Henry ruined my Arsenal career. Cheers T."
(L-R) Arsenal's Dennis Bergkamp, Thierry Henry and Patrick Vieira make up the defensive wall
Henry gave Ayling a baptism of fire in Arsenal training (Image: EMPICS Sports Photo Agency)
Following four seasons at Yeovil, Ayling transferred to Bristol City, where he remained for the subsequent two years. The chance to feature at Elland Road materialised in 2016, which he confessed caught him completely off guard.
Speaking to LUTV in 2020, he said: "To be honest, it came out of nowhere. It first got mentioned when Garry Monk got the job in that summer and Kyle Bartley was at Swansea, Bartley was coming on loan.
"I was in Thailand with him at the time, things weren't going well for me at Bristol, I knew I wasn't in their plans, I knew I'd have to find a new club to play every week. So I jokingly said to Kyle, 'Text Garry to see if he needs a right-back,' and nothing came of it, he ignored it.
"Then their first game, the right-back here – Berra [Gaetano Berardi] – who's still here, got injured, and I actually played the first game at Bristol City. I thought maybe I've got a chance to stay here and play.
Luke Ayling celebrates after scoring his sides first goal during the Sky Bet Championship match between Leeds United and Bristol City at Elland Road.
Ayling amassed almost 300 appearances for Leeds (Image: George Wood/Getty Images)
"I thought, 'I'm going to stay here.' Then there was a Carling Cup game on the Tuesday and I got left out of the squad and I was thinking, This isn't right.' Then on the Wednesday, I was up here signing and it'd all come around pretty quickly."
Ayling went on to spend nearly eight years at Elland Road, establishing himself as a fan favourite. Following 268 games for the Yorkshire club, he found himself struggling for game time under current manager Daniel Farke, prompting his temporary switch to Middlesbrough in January 2024.
The transfer became permanent that summer, though Ayling confessed the initial departure proved emotionally challenging. "Leaving Leeds hurt then, and to leave the boys I'd spent five, six, seven years with certainly hurt," he revealed on the podcast.
Luke Ayling of Middlesbrough is injured and goes off with head coach Michael Carrick
The 33-year-old will hope for a triumphant return to the Premier League this season (Image: Greig Cowie/REX/Shutterstock)
"I found it tough to leave at the time that I did. I still felt like I could help the team and get them to where they wanted to go. But it all came down to myself wanting to play football. It was either stay there for six months, sit on the bench or even not make the squad, or get out and play some football.
"I've been given a home at Boro and I'm really enjoying it." The defender has started both of Middlesbrough's opening Championship fixtures this campaign, with the side claiming victory without shipping a single goal.
They currently occupy second spot in the table alongside Stoke City and West Bromwich Albion as the only three clubs to secure maximum points from their first two outings. Meanwhile, his previous sides Arsenal and Leeds are set to clash at the Emirates Stadium this Saturday evening, with kick-off scheduled for 5:30pm.
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