'Arsenal coach said I'd never make it – I hope he watched me scoring for Liverpool'

You have to have a certain amount of quality to play for both Arsenal and Liverpool . But unfortunately for Jermaine Pennant , his potential largely went unrealised.

Signed by the Gunners as a teenager, Pennant had one of the best footballing educations a young player could dream of in and amongst Arsene Wenger 's legendary Invincibles squad. However, the former England Under-21 international's natural talent was sabotaged by his ill-discipline , even if he defied a hangover on his full Premier League debut to score a hat-trick against Southampton .

By the summer of 2006, a 23-year-old Pennant had already served a month behind bars for a drink-driving offence, played a game on loan at Birmingham City while wearing an electronic tag, and destroyed his relationship with Wenger after turning up late to training one too many times.

But that didn't stop Liverpool from taking their chances and signing him in a deal potentially rising to £8million. For all his misdemeanours, Pennant still had a point to prove at Anfield, where his former sides meet on Sunday for a 4.30pm kick-off.

It was a dismissive comment made by Wenger's right-hand man, Pat Rice, that stuck with him all the way from north London to Merseyside. Pennant recalled to The Guardian in 2017: “I definitely used it. He told my agent, ‘He’s not going to make it.’

"I don’t know if he had it in for me or if my personality was a bit rich. He’s old school, Pat, but I always believed I’d make it. At Liverpool , I said to my agent after scoring against Chelsea and playing in the Champions League final, ‘I wonder if Pat watched the game tonight?’”

Pennant netted his first Reds goal in a 2-0 home win over Chelsea in January 2007 and he started the Champions League final against AC Milan later that year as Rafa Benitez's side fell to a 2-1 defeat. But those were once again fleeting high points before the hype quickly fizzled out.

Following a loan spell at Portsmouth, Pennant departed on a free transfer to Real Zaragoza, where his old habits – namely poor timekeeping – quickly saw him frozen out in Spain. Stoke City offered him a return route to England, and boss Tony Pulis appeared to get something of a grip on his behaviour.

But the fact that Pennant, now nearing his 30s, was still trying to prove Rice wrong said it all about his career. “I saw Pat again when I played for Stoke against Arsenal a few times," he added.

"It was kinda frosty between us at the Britannia. We won 3-1 and I scored and ran past the Arsenal fans to rub it in. That was a good moment.

"For Pat to say, ‘You’re not going to make it,’ and then I play the Champions League final and score against his team, [it] was pretty sweet.”

After rounding out his playing days with spells at Indian Super League side Pune City, Wigan Athletic, Tranmere Rovers, Bury and Billericay Town, it's fair to say Arsenal legend Rice, now 76, was more right than wrong in his assessment of a young Pennant.

While the 42-year-old may well have moments he can reflect fondly on, his is a career that was ultimately defined by a significant amount of underachievement.

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