Pennant signed for Liverpool following Birmingham City's relegation in summer 2006, having shown flashes of promise during his time in the Midlands. (Source: BBC Sport) Having struggled with disciplinary problems during his time at St Andrews, including a thirty-day jail sentence for drink driving (Source: BBC News), Pennant's transfer to Liverpool appeared to be a make-or-break chance for him to prove his potential. Pennant's first season with Liverpool saw him establish himself as a regular, making 52 appearances across all competitions, including starting in Liverpool's Champions League final defeat to AC Milan. However, he never regained that level of consistency again, playing less than half that amount of games in 07-08, and just three League appearances in 08-09, before being loaned to Portsmouth. Pennant, despite being initially well liked by Benitez, eventually became a victim Liverpool playing with a three man forward line of Dirk Kuyt, Steven Gerrard and Ryan Babel, and latterly Albert Riera. With no wingers Pennant found his role increasingly diminshed, and he never reached the levels he had hoped for.
