Naz Majeed

As far as full Premier League debuts go, it is hard to top the one enjoyed by Jermaine Pennant for Arsenal in 2003. A hat-trick against Southampton is as good as you could have asked for, and at the time this seemed to be the anchor around which the young winger could build his Highbury career around after signing for the Gunners for a record fee as a 15-year old 4 years earlier. It proved to be a false dawn, however.

“I did OK to score a hat-trick: it shows I had talent, though it helps when you’re playing with Thierry Henry and Patrick Vieira. That was the first game of Arsenal’s 49-game unbeaten run.”

Speaking in 2018, Pennant revealed he did not even expect to play in the game, and was wholly unprepared for the start, especially as he had featured mainly in secondary cup competitions in his time at Arsenal under Arsene Wenger.

Part of a squad that boasted the talents of Freddie Ljungberg and Robert Pires (who also scored a hat-trick in that same match), the then 19-year old imagined he would be named on the bench at best.

And so his performance came as a surprise to all involved, but what may have surprised those watching was that it was the pinnacle of his time at Arsenal, and would be one of the few bright spots in a journeyman career.

Loan spells at Watford, Leeds, and Birmingham City followed, Pennant technically contracted to Arsenal during the Invincibles season but not featuring at all during their most glorious of title runs. Despite off-the-field issues, Pennant did enough to convince Birmingham manager Steve Bruce to push for a permanent deal, Arsenal agreeing to the transfer at the end of the 2004-05 season to allow Pennant to stay on at St. Andrew’s. More issues followed though, and Birmingham were relegated in 2005-06.

In what seemed a strange transfer, Liverpool made a move for the winger, Rafa Benitez signing Pennant as part of an influx of players that included Dirk Kuyt, Craig Bellamy, and Fabio Aurelio.

In total Pennant played over 50 times that season in all competitions, including scoring against Chelsea and starting in the Champions League Final against AC Milan in Athens. Unlike the miracle of Istanbul, however, Liverpool would not lift the trophy that season, and Pennant was again left with disappointment.

Pennant moved to Real Zaragoza in 2009 but failed to impress fans at the Aragonese side as they struggled in La Liga. He did himself no favours by again lapsing into disciplinary issues, turning up late for training on several occasions and his time there is perhaps best summed up by what he did upon leaving the club to sign for Stoke City in 2010.

"I had to take a train to Madrid to fly to Manchester to sign the agreement with Stoke City, I was going to miss the train, so I just left my Porsche Cayenne there [in Zaragoza] and left the keys in the glove compartment. I knew I wasn't going to go back, I didn't feel too bad to leave such an expensive car; I told my translator Fernando to go to the station and get the car."

By now a disturbing pattern had begun to emerge, that of a talented player that could not stay out of trouble. Now at Stoke under the Tony Pulis, however, some had believed Pennant had the opportunity to get his career back on track, and in the latter half of the season, he showed glimpses of the potential that Wenger had first seen so long ago, with impressive performances including scoring against Arsenal and setting up a goal in the FA Cup Semi-final.

The Wembley Final was yet another major occasion where Pennant was handed a start, and proved to be another loss on his CV, the 1-0 win for Manchester City marking the start of their own era of dominance in the English game, while Pennant himself eventually being loaned to Wolves after falling out of favour with Pulis. Even with a change of manager as Mark Hughes took over in 2013 did little to help his cause, however, and Pennant was eventually moved on once more.

Spells at Pune City in India (finishing 6th in the Indian Super League) and Wigan Athletic (relegated to League 1) followed before in 2016 Pennant found himself signing for Tampines Rovers in Singapore, accepting a massive pay cut to play for the 5-time S-League champions. 

Pennant did not manage to win the league in Singapore, finishing in second place.

He moved back to England in 2017 with Bury in League 1, though once more failed to make an impact, the most noteworthy incident involving a large amount of money reportedly stolen from his locker at the club (which has since been expelled from the Football League due to financial mismanagement). He then moved to the Isthmian League, signing for Billericay Town, a side that has been in existence for 130 years but has never progressed past the First Round of the FA Cup. He lasted four months, unable to break into the first team.

“I was always pressing the self-destruct button. I knew I was doing it, but I wanted to know why I was doing it.”

An illuminating line from his autobiography titled Mental, Jermaine Pennant has been everything from wonderkid to washout, playing in the UEFA Champions League Final to being knocked out of the AFC Cup, and gaining the trust of Arsene Wenger to appearing on reality TV.

The story of Jermaine Pennant a strange tale, taking a once-shining star to strange places, every step perhaps accompanied by a shadow and spectre of disappointment. With no major honours to speak of, Pennant has been involved with more controversial incidents than he has league goals.

This is a player whose debut brilliance sparked Arsenal’s best-ever run, but was not part of the side that actually won the Premier League. A player that featured in FA Cup and Champions League Finals and who could not force his way into a team whose record attendance is below 5000 people.

A player that has been in prison, and yet once seemed to have all the potential in the world, but could never quite deliver.