Having famously been Chelsea's last proper regular from the academy prior to Frank Lampard's appointment, Terry was asked on Instagram Live who the most talented player was to have not made the grade during his time at the club.
"Probably a boy called Rob Wolleaston at Chelsea," he began.
"He was like a midfielder/winger, had so much ability.
"I still know Rob now, but mentally didn't have that to go and push himself.
"He got chosen to train with the first team at a really young age, 17 or 18, did really well and Gullit told him he was going to play in the first team in a cup game.
"He then phoned up on the day of the game and said he was sick.
"All of us, if we were sick or felt like we were at the end of the world, we would have still gone and played the game, we wouldn't have given up that opportunity.
"He actually done it two or three times and he was just not mentally ready for the game, but ability-wise, incredible."