A former Liverpool winger has opened up about the unusual way his transfer to Liverpool unfolded, revealing that Steven Gerrard effectively tried to ‘tap him up’ during a Premier League game.
Anfield legend Gerrard made 710 appearances for Liverpool over a 17-year career with the senior team, having risen through the club’s youth ranks. He scored 186 goals and won two FA Cups, three League Cups, a UEFA Cup, and the Champions League.
After leaving Liverpool in 2015, Gerrard spent two years in the MLS before embarking on his managerial career back at Anfield with the academy team, but it appears the former England international always had a keen eye for talent — even when on the same pitch.
Speaking on the Under The Cosh podcast, ex-Liverpool winger Jermaine Pennant revealed how Gerrard approached him during a match, asking a question that left him stunned.
“We were both in midfield and he’s come jogging past and he’s said, ‘Alright, lad, who’s your agent?’ And I’ve replied, ‘Oh, he’s name is Sky Andrew’. Then he just ran off.
The game’s going on and I’ve just lost all thought. Why is he saying that? Where’s the ball? F–k the ball, and I’ve started chasing him.”
Pennant couldn’t resist pursuing the conversation further, even if it meant breaking positional discipline on the pitch.
“The ball went out and I’ve run right across. Steve Bruce is thinking, ‘Where’s he going? He’s supposed to be right wing’.
So I’ve gone back over to Stevie and the balls thrown in, and now I’m pretending to mark him. Then I’ve said, ‘Stevie, Sky Andrew — do you know him? Do you want his number?'”
The former England U21 international’s breakthrough came in 1999 when he was snapped up by Arsenal from Notts County for a staggering £2 million — a record fee for a 15-year-old in England. This hefty investment reflected the belief in his potential to become a future star.
Yet, the reality of breaking into Arsenal’s first team proved challenging. Pennant’s early career was marked by a series of loan spells at clubs such as Watford, Leeds United, and Birmingham City, where he struggled to consistently showcase the talent he had promised. By the mid-2000s, many questioned whether the young winger would fulfil his early potential.
The 2005–06 season, however, marked a turning point. Now a Birmingham City player, Pennant’s performances began to attract attention once again. His pace, dribbling, and creativity rekindled memories of the promising youngster who had once dazzled scouts and coaches alike.
As Birmingham fought a tough battle against relegation, the Pennant’s form was one of the club’s few bright sparks and it was enough to draw the gaze of Liverpool — a club renowned for spotting and nurturing English talent.
Birmingham City’s relegation at the end of the 2005–06 season conveniently cleared the way for Pennant’s big move and the Reds lodged an official bid, signing the winger for £6.7 million that summer.
Over three seasons at Anfield, Pennant made 81 appearances, winning the 2006 Community Shield and coming close to European glory as part of the team that finished runners up in the 2006–07 Champions League, narrowly losing 2-1 to AC Milan. His final season saw him loaned out to Portsmouth before a permanent transfer to Real Sociedad in 2009.
Looking back, Pennant’s anecdote about Gerrard’s mid-game ‘tap up’ offers a rare glimpse into the informal, behind the-scenes dealings that can make big transfers happen. It also highlights the respect Gerrard had for Pennant’s ability a nod from one Liverpool legend to a talented teammate in the making.
