The talkSPORT co-host spent 10 years in charge of boyhood club Crystal Palace between 2000 and 2010.
And while discussing the future of world-renowned golfer Tiger Woods following speculation that he could be set to retire following The Open at St Andrews.
While first suggesting Woods has no reason to quit the sport he loves, the conversation quickly turned to his experiences with Palace.
Asked by host Sam Matterface if he's ever had to tell a player he was no longer needed, Jordan said: "Yeah, to Dougie Freedman who was an absolute mainstay at Crystal Palace and one of my best signings, but the time had come.
"Dougie's future wasn't with us any more and off he went to Leeds United in a different direction of travel.
"I had great delight in saying it to Neil Ruddock because we couldn't take any more bathroom scales that he stood on and broke."
Freedman spent two spells at Crystal Palace, the first coming in the 1990s, but his second stay lasted eight years, leaving for Elland Road in 2008 after 237 appearances.
Ruddock, meanwhile, was coming to the end of his career.
The defender had played for Liverpool, Tottenham and spent one season at Selhurst Park in 2000 and finished his career at Swindon in 2003.
Asked about his experience of retiring, former England and QPR winger Trevor Sinclair said: "For me, I knew it was my time," he said recalling his time at Cardiff City.
"I had my fourth and fifth knee operation when I retired [in 2008]. My last game was the FA Cup final.
"I woke up one night at 2 in the morning and my knee was killing. It was before Christmas, I'd been injured for ages and I just thought that I can't keep doing this to myself.
"You're a long time retired. You want to spend time with your family, you want to be active and do things that other people do."