Tottenham manager Harry Redknapp has admitted that he was forced to release Jonathan Woodgate.
Woodgate suffered an injury-riddled three-and-a-half year stay at White Lane and was freed by Spurs in the summer when his deal expired.
He was snapped up by Stoke City and has started the season in good form, proving his fitness in the process.
"I wanted to keep Jonathan. I wouldn't have let him go," said Redknapp, whose side take on Woodgate's new team in Tuesday's Carling Cup third-round clash at the Britannia Stadium.
"I asked him to come back to train but the secretary said he couldn't because of the insurance. That was the problem.
"He was convinced he was fit again.
"It was gutting but I can see the club's point of view. He had barely kicked a ball in two years."
An own goal against Sunderland aside, Woodgate has made a good impression at the Britannia Stadium and Redknapp hopes the former England defender can get back to his best.
"If he can stay fit he is one of the best. He and Ledley King are up there with the John Terrys and Rio Ferdinands of the world," said Redknapp, who was also reluctant to let Peter Crouch and Wilson Palacios join Stoke this summer.
"I like Crouchy as well. He wasn't one I was mad to get rid of.
"Wilson's deal was dependent on Crouchy going. I was looking at the time to bring Gary Cahill in and we needed to raise some money to do that, and bring in Scott Parker, so we ended up getting around about £20million for the two."