James injured his hamstring during the defeat to Newcastle United last Saturday and missed the loss to PSG at Stamford Bridge this week.
The England star has been plagued with injuries his entire career and now faces up to 6 weeks once again as he recovers in the medical room, somewhere he is used to being.
Manager Liam Rosenior said the news was “really frustrating and disappointing” especially after the defender signed a new deal.
Speaking to BetVictor, Waddle suggested that James may be remembered as being injury prone instead of a great player in the future.
“He is one of the very best in his position, but James’ injury situation is just unbelievable.
“But there's something about him where you just think, injury after injury. And you've got to say that unfortunately for him, it's hindered his career a lot, England-wise.
“Even Chelsea-wise, people talk about him being a great right-back, and yes, he is when he's fit and when he's 100%, he is a great right-back, but we don't see enough of him.
“When fit, he would definitely be in the England team, wouldn't he? Let's be honest. So, I do feel for him.
“There's just something about his body that can't take the strain of game after game after game. It's unfortunate that he will go through his career where people will say, ‘Great player, but never fit.’”
Malo Gusto is likely to be playing the majority of games in his absence as the side head into the international break where James will also miss out an international call-up to England for their friendlies this month.