David managed to tempt the Italian star into the Premiership from Scottish giants Celtic when he was manager of Sheffield Wednesday back in August 1997.
The manager-player relationship only lasted until November 1997 when David left the Yorkshire club.
Di Canio departed Hillsborough after the now infamous pushing incident on referee Paul Alcock. Harry Redknapp snapped him up in January 1999 and he hasn’t looked back since.
Three years down the road and their paths will cross again when we travel to Upton Park on Wednesday night.
Di Canio, of course, is the man of the moment after scoring the goal that knocked Manchester United out of the FA Cup. And it is clear David remains a big fan of his enigmatic talent.
Here David talks about his time as Di Canio’s manager and beyond:
"Earlier this season I saw one of the best exhibitions of forward play at West Ham when I watched them play Leicester City. Unfortunately they had a man sent off which gave the initiative to Leicester. It was a period where West Ham had started poorly but were showing signs that they would improve.
"Paolo Di Canio was absolutely outstanding in that game. His touch with both feet was splendid, his movement was excellent and I felt then that West Ham had rejuvenated him.
"Paolo was a player I signed with some difficulty from Celtic.
"He was a player I had clearly in my thoughts - I’d been to Scotland to watch him, he had a massive talent and, in fact, sometimes he made things too difficult.
"In Scotland he was able to drift past people and overdid things at times but he did that because he knew that he was in a different league and thought process to some of the other players that he was playing with.
"It was a wonderful deal for Sheffield Wednesday. We sold a player who we brought for £200,000 in Reggie Blinker, he went to Celtic, Paolo came here for £1.7m.
"He turned out an exciting player but also a player who could be broody.
"I bought him to combine with and help out Benito Carbone. Paolo teamed up with Benito and I sometimes look back and wonder whether or not it was in Wednesday’s best interests that we had these two exciting players together in the same camp.
"One particular exhibition in one of my last games at Sheffield Wednesday was a 2-2 draw at Aston Villa when they played up front in superb fashion. Some of the football that day was super.
"But by the same token they played together at Manchester United in a heavy defeat, we weren’t good enough to get the ball to their feet and we took a heavy beating, and I substituted them both.
"Paolo is an exciting character, he has tremendous gift to be able to spot a pass, his crossing is superb and he finds that scoring goals comes naturally.
"He is one of the finest talents around and he was an ideal signing for Sheffield Wednesday in the circumstances when they needed a player to put bums on seats.
"Unfortunately after I left things went down and amidst it all Paolo became irritated and frustrated, culminating in his problems with Mr Alcock.
"I’m delighted for Paolo, that he is playing so well. It is always nice when a crowd has a player to hang its hat on and the East Enders have taken Paolo to their hearts.
"There is always a chance that he will grow frustrated and look for new pastures because that is the style of Paolo over his career.
"But I would have thought many supporters would willingly swap a year of his talents for three years of mediocrity."
Few men inside English football know Paolo Di Canio as well as our director of football David Pleat.