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Drama has never been far away from the Italian during a colourful career that began with Lazio nearly 30 years ago, and he wrote another chapter of his story on Monday when he released a statement saying he had resigned from his post.
The 44-year-old, who guided the Robins to promotion in his first season in charge last term, has grown increasingly tetchy about the boardroom goings-on at the County Ground an decided on Monday night that enough was enough.
Town have been the subject of a takeover bid for some time and Di Canio, who claimed to have first tendered his resignation last Tuesday, had pledged to stay if the deal was ratified by the Football League by 5pm on Monday.
No transaction was confirmed, though, and the former West Ham striker issued a statement through his agent, Phil Spencer, confirming he had quit.
"Last Tuesday, 12th February, I formally confirmed my resignation as manager of Swindon Town Football Club with immediate effect," said Di Canio.
"There have been a number of broken promises made by the club over the time that I have been manager of Swindon Town.
"Despite these problems, I have delivered everything and more that was asked of me, by achieving promotion last year as champions and competing this season for promotion to the Championship and being just three points from top place a year earlier than expected.
"I did not resign immediately, nor publicise my resignation after I had formally confirmed it as I did not want to jeopardise the negotiations for the sale of the club and I wanted to listen to what the proposed new owners plans were.
"Following discussions, my representatives put forward a proposal that would secure my future at the club until at least the end of the season and quite possibly beyond as well.
"This proposal actually reduced the club's contractual liabilities to me in the interest of saving Swindon Town FC. At a meeting last Friday the proposed new owners accepted and said they were very happy with the new terms.
"I entered into a temporary arrangement with the proposed new owners to continue in my role as manager but all this was agreed subject to Football League approval for the purchase of the club being granted by 5:00pm on Monday 18th February.
"At the time of issuing this statement, I have had no further contact from the proposed new owners and I have been told that unfortunately Football League approval has not been granted yet and therefore my temporary arrangement has ended and my resignation stands."
When asked to clarify Di Canio's resignation, a Swindon spokesman told Press Association Sport they were unable to expand on the statement.
One of Di Canio's bugbears was the sale of Matt Ritchie to Bournemouth without his consent, a move indicative of the simmering tensions in Wiltshire.
Di Canio's success in the dugout has shocked some, with a number of observers considering him too hot-headed to manage a team.
As a player he courted controversy by pushing referee Paul Alcock to the ground while at Sheffield Wednesday, while he also had a number of disciplinary issues when at Celtic.
He joined Celtic in 1996 after an 11-year spell in his homeland where he struggled to establish himself with the likes of Lazio, his boyhood team, and AC Milan.
He left Wednesday for West Ham where he became a legend in the eyes of the United fans, scoring one of the Premier League's most memorable goals against Wimbledon.
After parting company with the Hammers he went to Charlton, before an emotional return to Lazio, although his time there was stained by his support of fascist movements and his association with the club's Ultras.
He retired from playing in 2008 and leaves Swindon sixth in League One, three points off top spot.
Swindon's current board eventually acknowledged Di Canio's resignation via a statement posted on their official website just after 10:30pm.
They gave a nod to the situation surrounding Ritchie and said that Di Canio's assistant, Fabrizio Piccareta, will take the team against Tranmere on Tuesday.
The statement added that Piccareta would be in charge until the ownership situation has been cleared up, possibly hinting that Di Canio could yet return.
The statement read: "The board are disappointed that Paolo Di Canio has made the decision to resign at such a critical time for Swindon Town Football Club.
"We are also disappointed that the sale of the club has yet to be approved, but we hope the outstanding issues with the Football League will be resolved within a short period of time.
"It is worth noting that Matt Ritchie was sold due to the tremendous financial pressure the club is facing and in order to continue operating whilst the sale of the club went through.
"We understand the prospective new owners had reached agreement with Paolo Di Canio on bringing in loan players to strengthen the squad for a final push for the Championship.
"Until the situation has been resolved, Fabrizio Piccareta will be in temporary charge of the team as we travel to Tranmere Rovers tomorrow, where a win would see Swindon become leaders of League One.
"The board shares the fans' tremendous frustration at the events of the last few weeks and is determined to resolve these issues to ensure the best outcome for the club."
Paolo Di Canio factfile:
1968: Born July 9 in Rome.
1985: Joins home-town club Lazio, then in Serie B, but does not break into first team.
1986: Drops down a division to Ternana, playing 27 matches and scoring two goals in 1986-87.
1987: Returns to Lazio but again fails to make a first-team appearance as they win promotion to Serie A.
1988: Makes his Serie A debut for Lazio in October and plays 30 times that season, scoring one goal.
1989: Plays 24 matches, scoring three goals.
1990: Moves to Juventus and scores three times in 23 appearances.
1991: Plays 55 games over the next two seasons, hitting three goals.
1993: Heads south to Napoli, making 26 appearances and scoring five goals.
1994: Returns to Juventus but moves on to AC Milan without playing a league game.
1994: Restricted to just four starts at Milan. Makes another 11 appearances from the bench and scores one goal against Fiorentina in January.
1996: Leaves the San Siro in June to join Celtic in a £1million deal.
1996: Becomes a firm favourite with Celtic fans, scoring 12 goals in 26 league games as the club finish runners-up to Rangers in title race. In total scores 15 times in 37 matches.
July 9 - Breaches his contract by refusing to join his Celtic team-mates at their Dutch training camp and Celtic threaten him with a three-year ban.
July 15 - Announces his intention to quit Celtic after new coach Wim Jansen says he is unimpressed with the player's attitude in training.
August 6 - Joins Sheffield Wednesday in a £4.5million deal. Scores 12 times in Premiership to finish the club's top scorer.
September 26 - Pushes referee Paul Alcock to the ground after being sent off in the clash with Arsenal at Hillsborough.
October 23 - Receives 11-match ban from the Football Association, including a statutory three matches for being sent off in the previous month's game against Arsenal. He is also fined £10,000.
November 3 - Wednesday reveal they have imposed their own fine on Di Canio for his dismissal and push on Alcock, believed to be two lots of two weeks' wages, totalling £68,000.
December 12 - Wednesday suspend Di Canio for two weeks without pay when he does not return from a break in Italy. Later says he is suffering from stress and depression.December 26 - Is suspended for a further two weeks and docked another two weeks' wages by Wednesday when he fails to appear for home game against Leicester.
1999: January 9 - Is suspended and fined another two weeks' wages by Wednesday.
January 19 - Declared fit after Wednesday receive report into his health. But Wednesday refuse to pay Di Canio the £102,000 he was fined while he was in Italy claiming he was ill.
January 27 - Joins West Ham for £1.7million.
February 9 - Charged with misconduct by FA in relation to incident during Premiership game with Villa when he appeared to make an insulting gesture. Later fined by the FA.
2001: November 29 - Awarded FIFA's Fair Play Award for 2001 in recognition of his "special act of good sportsmanship" in West Ham's game at Everton the previous season.
2002: January 6 - West Ham boss Glenn Roeder confirms Manchester United made a bid for the player which the club rejected.
2003: August 11 - Signs a one-year deal with Charlton as a free agent.
2004: Returns to former club Lazio, but his relationship with the club's Ultras generates negative headlines.
2006: Sees out his career with Cisco Roma, retiring in 2008.
2011: May - Appointed Swindon manager.
2012: April - Swindon are promoted from League Two with 93 points, having lost the Football League Trophy final against Chesterfield.
2013: February 18 - Resigns as manager citing issues with the club's hierarchy.