Pleat, now the caretaker coach at Tottenham, signed Di Canio for pounds 4.5m from Celtic in the summer of 1997. However, he soon realised that the striker with "fantastic ability but a very short fuse" would not be around for long and Saturday's attack on referee Paul Alcock looks to have ensured his premature departure.
"I don't think there is any doubt about it now, this is the third manager he's played under there," Pleat said. "Paolo was incredible, he worked very hard in training and he loves the game. But he's a bit of a gypsy, he never played for any club for too long."
The 30-year-old striker, who had only just patched up his differences with Danny Wilson after being labelled a "fancy dan" by the Wednesday manager, now faces a misconduct charge from the Football Association as well as being suspended by his club.
"When he was at Celtic, I spoke to Tommy Burns about him, as a person and as a player," Pleat told Radio 5 Live. "He didn't have any problems like fighting but he had this temperament problem where he wanted to argue with referees' decisions and throw his hands in the air.
"And while he was throwing his hands in the air and making gestures, the free-kick has been taken and your team is defending one man short.
"He is not easy to cope with in a team situation because he only sees things through his own eyes, he can't see them for the good of the group rather than himself.
"I don't think Paolo was one of those people who wanted to fight people and hit people. He just had a kind of theatrical temperament, maybe something to do with his background."
Pleat recalled an amusing incident between Ron Atkinson, his successor at Wednesday, and Di Canio. "After one particular game away from home, Ron accused him of being a part-timer - in other words he plays when they are at home but he doesn't put in so much when they are away from home.
"And Paolo said: `No, no, no! I am full-time, I train every day, I come every day - it is you that is the part-timer, you only come in occasionally!' "
On a day when allies were thin on the ground, Di Canio found support from Benito Carbone, his fellow Italian and Wednesday team-mate.
"He likes his work, he likes everything in England," Carbone said, "and now I think he cries for what he has done."Reuse content