The former Reds winger was playing for Birmingham City at the time after moving from Arsenal the previous year. In his youth, Pennant, now 41, was considered one of the brightest talents in English football, especially after becoming the most expensive 15-year-old in history when the Gunners snapped him up from Notts County for £2million in 1999.
However, he struggled to live up to expectations at Highbury and had a string of lacklustre loan stints, leaving his career somewhat in the doldrums by the mid-2000s. His form, however, picked up at Birmingham during the 2005/06 season, prompting covetous glances from the red half of Merseyside.
Rumours of a move to Anfield were running rife, and when Gerrard ran over mid-match to ask Pennant who his agent was, he knew their interest was legitimate. “He [Gerrard] knew I was a good player,” Pennant said on talkSPORT, “because he half tapped me up in one game.
“I was playing against Liverpool and he came running over to me during the game, saying, ‘Who’s your agent?’ I said it was Sky Andrew and that was the last thing he said – I was bamboozled,” he recalled. “So I ran over to him and said, ‘Do you know him?’
“At this time, the game is going on. The ball’s gone out of play. He just went to me, ‘Who’s your agent?’ And I was with Sky Andrew at the time. And he said, ‘Okay, lad’ – and then ran off. My brain was frazzled. I’m thinking, ‘Why’s Steven Gerrard asking me this?'”
The Blues were embroiled in a relegation dogfight at the time, but that didn’t stop Pennant from abandoning his post to pry a little more information from the Liverpool skipper. “[Birmingham boss] Steve Bruce is probably looking thinking, ‘Where’s Jermaine going? Why is he peeling off to the left – he plays on the right!’ But I’ve gone off to speak to Steven Gerrard!
“So I said to him, ‘Why, do you know him?’ He’s gone, ‘Nah, nah, nah’. Then I’ve said, ‘Do you want his number?’ So after the game, I phoned my agent and I said, ‘Steven Gerrard wants your number. Do you know him? Get his number! Call him!'”
In the end, Birmingham couldn’t stave off relegation, which in hindsight worked out perfectly for Pennant. Liverpool came knocking that summer, and snapped him up for a cool £6.7m.
He ended up spending three seasons at Anfield, making 81 appearances. His time at the club saw him pick up a Community Shield winners’ medal in 2006, and nearly reach the pinnacle of European football with a defeat to AC Milan in the final of the Champions League in 2007.
Pennant gradually lost his place in Liverpool’s first team setup following the attacking arrivals of Fernando Torres, Ryan Babel, and Albert Riera, and spent his last season at Liverpool on loan at Portsmouth, before leaving permanently for Real Sociedad in 2009.
