The former midfielder, 37, spent five years in Arsenal's academy as a teenager and was one of the hottest young prospects in the country. But a falling out with Gunners academy director Liam Brady sparked a cross-town move to Spurs - the club he'd supported since he was a boy.
"I was the best player [at Arsenal]," O'Hara claimed on the Ben Heath Podcast. "I believed I was going to play for them. They were the best side with the best academy. Arsenal loved me, I was the one everywhere was talking about who was coming through and was going to be [their next star]."
The Gunners tried to tie him down to a professional contract when he turned 17, but after being told by Brady that he wouldn't get into the first team until he was 21, O'Hara decided to leave. "I thought I was ready, I wasn't ready, but I didn't want to get held back... I didn't want to wait four years."
Interest in him ramped up once he became a free agent, with Manchester United, Manchester City, Chelsea and even Real Madrid offering him trials, but O'Hara opted to join Spurs instead. "I was a Tottenham fan," he added. "I used to train at Arsenal in a Tottenham shirt.
"I never wanted to leave home, I lost my mum at 17 and she was going through cancer at the time, so Tottenham was the perfect opportunity. But the funny thing is, I went to Tottenham based on the fact I didn't want to wait until I was 21 to make my debut for Arsenal, but I didn't make my Tottenham debut until I was 21 (laughs)."
O'Hara made his first team debut in the 2007/08 season after a successful loan spell at Millwall. He became a first-team regular under Juande Ramos, but Harry Redknapp's arrival a year later pushed him to the peripheries of the squad.
Jamie O'Hara was one of Arsenal's most highly-rated youngsters
Loan spells at Portsmouth and Wolves followed before he joined the latter on a permanent basis in 2011. Shortly after his career went into free-fall. After suffering back-to-back relegations with Wolves he spent seasons at Blackpool, Fulham and Gillingham before dropping into non-league football in 2016. He hung up his boots in 2020 aged just 33.
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