Liverpool manager Rafael Benitez accepts signing Jermaine Pennant is a 'risk' and that the £6.7million winger has been given his last chance at a big club.
Pennant joined from Birmingham on Wednesday and is now at the club's training camp in Switzerland, preparing for a likely debut against Kaiserslautern in Liechtenstein on Saturday.
Benitez is fully aware he has been questioned over the wisdom of signing of a player who served a prison spell last season and has had a string of problems off the field.
But the Spaniard - who has now spent more £13million this summer on two of football's problem players - likened the situation to his recent capture of striker Craig Bellamy.
The Wales international faces a court appearance in his native Cardiff later in the year and he too arrived at Anfield with plenty of baggage.
'We know it's similar to Craig Bellamy because this is Jermaine's last opportunity to show he is a good player at a really big club,' said Benitez.
'When you sign a player that's been at a big club before but had problems, you know he will think more about the consequences of everything he does, and that's a positive thing.
'Of course there is some risk in the deal, but there is risk in every transfer. It doesn't matter who you sign, you must wait and see if it's successful.'
Benitez added: 'These players know more about the importance of doing the right things. It's a big motivation for them to hear people say they're more mature, are different and have the quality to play for a top club.
'It's easier to sign a player who everyone knows is good and has never had any problems, but I believe when a player changes, shows he is more mature and proves to everyone he has the quality and the ability to end any problems, that makes him an even better player and person.'
Benitez told the Liverpool Echo: 'Jermaine wants to show everyone he can be a contender at a big club again and the most important thing for me is we are signing players with a lot of quality who we feel have learned a lot from their experience.
'At Liverpool we have an atmosphere in the dressing room and throughout the club which will help players like Jermaine and Craig.
'They understand what's expected when you sign for Liverpool, so we're sure there will be no problems.'
Pennant, 23, was signed by Arsenal as a 16-year-old for £2million but failed to hold down a place in Arsene Wenger's side and spent time on loan at Watford, Leeds and Birmingham before the Midlanders spent £3million on him a year ago, just at the time that the Nottingham-born player was facing jail.
'Jermaine is a player we've liked for some time. He makes a lot of assists, is a good crosser and has a lot of pace,' said Benitez.
'He's the kind of right winger we've been looking for. He also has the advantage of being used to the English style, which means he'll have no problem adjusting.'