Thierry Henry ruined my Arsenal career – but my time at Leeds left me hurt

Luke Ayling (L) revealed the influence Thierry Henry had on his Arsenal career (Image: Arsenal FC via Getty Images)

Luke Ayling revealed the impact Thierry Henry had on his Arsenal career almost 15 years after he was left "hurt" over his emotional Leeds United departure.

The 33-year-old came up through the ranks of the north London side and spent a decade at the club. It was in July 2009 that Ayling signed his first professional contract following his starring role in Arsenal's double-winning youth team of the 2008/09 season.

Aged 16, he was given a rude awakening to the men's game when he was asked to mark the legendary Henry in training . Discussing the ominous task he was handed, he told 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 achievements in the academy, Ayling only appeared in a first-team matchday squad once for Arsenal and left the club in 2010 without ever making a senior appearance. He signed for Yeovil Town to spell an end to his 10-year association with the Gunners, and offered a joke surrounding Henry's role in his exit as he said: "Henry ruined my Arsenal career. Cheers T."

After four years in Yeovil, Ayling made the move to Bristol City, where he spent the next two years of his career. It was in 2016 that the opportunity to play at Elland Road came about, and it was one he admitted emerged out of the blue.

Henry was a menace for any defender in his prime, let alone a teenager (Image: Getty Images)

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.

Ayling spent eight years at Leeds United before leaving for Middlesbrough (Image: Robbie Jay Barratt - AMA/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 ended up enjoying an almost eight-year career at Leeds, becoming a fan favourite. After 268 appearances for the Whites, he lost his place in the side under current boss Daniel Farke, which led to his loan move to Middlesbrough in January 2024.

The move was made permanent that summer, but Ayling admitted the initial exit was difficult to take. "Leaving Leeds hurt then, and to leave the boys I'd spent five, six, seven years with certainly hurt," he said on the podcast.

The 33-year-old will hope for a Premier League return this season with Middlesbrough (Image: Getty Images)

"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."

He's since started both of Boro's first two games of the season, which they've won without conceding a goal. They sit second in the Championship table and are joined by only Stoke City and West Brom in earning wins in their opening two fixtures, while his former sides Arsenal and Leeds meet at the Emirates Stadium on Saturday for a 5:30pm kick-off.