Newcastle boss Sir Bobby Robson has told BBC Sport he thought long and hard before deciding to pursue Lee Bowyer.
Bowyer's signing will cause controversy
Bowyer agreed terms with the North East side last week and is expected to sign a four-year deal this week.
The 26-year-old will join up with former Leeds team-mate Jonathan Woodgate, who were both embroiled in a much-publicised court case after an Asian student was attacked in Leeds city centre.
While Woodgate was eventually found guilty of affray, Bowyer was cleared of all charges.
Robson admitted to BBC Radio Five Live's Sportsweek programme that the signing was as hard a decision as he has made in his long management career
"We had to give it a lot of consideration," Robson told BBC Radio 5 Live.
"Lee knows he made an error. But there's a saying he needs a second chance."
Robson believes that bringing Bowyer, who has been released by West Ham, will be a key acquisition for the Magpies.
"We're trying to make some indentations in the Premier League with Arsenal and Manchester United dominating the scene.
"Lee Bowyer is a fine player and there's no doubt, in my opinion, about that.
"He'll be a massive addition to my squad
"We've beaten a lot of other Premier League sides that were very keen to sign him.
"I think he will have a good, long career with us."