The outspoken agent has always caused controversy but his handling of the AC Milan goalkeeper's contract negotiations has been shockingly amateurish When Zlatan Ibrahimovic was looking to leave Ajax, he asked Thijs Slegers if he could recommend a new agent for him.
"There are two I can think of," the Dutch journalist replied. "One of them is the firm that works for [David] Beckham; they're supposed to be terrific.
"And then there's another guy. But, well...
"Well, what?" Zlatan enquired, his interest already piqued.
"He's a mafioso," Slegers said.
"Mafioso sounds good," Ibrahimovic enquired.
It's fair to say that the Swede took an instant liking to Mino Raiola, the straight-talking agent who was prepared to do whatever was required to get his clients whatever they wanted.
Ibrahimovic wrote in his autobiography, "The guy wasn't actually a mafioso. He just looked and acted like one... He was completely fearless and prepared to pull any number of tricks."That is beyond doubt. Two years after Ibrahimovic left Ajax for Juventus, the fallout from Calciopoli led to the release of the following recorded telephone exchanges between then Bianconeri managing director Luciano Moggi and Raiola from the striker's final days in Amsterdam:
Moggi: "You and Ibra continue to make trouble. Don't send him to training ..."
Raiola: "Tomorrow, I'll keep the player at home all day; he won't show up for training. I then have an appointment with the directors of Ajax at noon, but I'll come at two..."
Ibrahimovic had no issue with acting up in order to push through his move to Turin. As he explained, "I didn't want another 'nice' boy [for an agent]. I wanted to be transferred and to get a good contract."
Raiola delivered on both counts. He also came through for Paul Pogba last year, facilitating the midfielder's record-breaking move from Juve to Manchester United, and making a reported £41 million for himself in the process.
Raiola is now in the headlines again due to Gianluigi Donnarumma's refusal to sign a new contract at Milan - but this time around the coverage has been nothing but negative.
Raiola, of course, has always been largely unaffected by name-calling and accusations of greed but this time it is not just his client's reputation that is being ruined, but also his own.
Even those who don't particularly like Raiola have always grudgingly respected him, conceding that he is a master manipulator of the transfer market.However, his handling of Donnarumma's break-up with Milan has been horrendous, both surprising and embarrassing in its amateurish.
First, there was the bizarre press conference in his kitchen in Monte Carlo, replete with vague, unsubstantiated claims that Donnarumma had been bullied by Milan and even subjected to death threats.
Then, on Sunday, Donnarumma reacted to reports that he was set to part company with Raiola by declaring his support for his under-fire agent: “#Donnarumma #Raiola Yesterday, Today and Tomorrow!” he wrote on Twitter.
Raiola was enthused, replying "DONNARAIOLA x HATERS. 1-0. What's next?"
Unfortunately, the answer to that question was absolute farce, as Donnarumma stated that he would discuss a contract renewal with Milan after the European Under-21 Championship, only to then claim that his account had been hacked.
In spite of everything, it is difficult not to feel some sympathy for Donnarumma, an 18-year-old who has found himself at the centre of what Italy boss Giampiero Ventura has called "a TV drama" even before the weekend's plot twists.
Unsurprisingly, Donnarumma seems to have been affected by the furore: He has been nicknamed 'Dollarumma', had fake banknotes thrown at him before Italy's Euros opener against Denmark and his performances in Poland have been poor.
Family members have also pleaded for an end to the abuse that both they and Gigio have received on social media.Still, there is hope that the situation will be resolved and Donnarumma will continue with the club he has supported since childhood. Both Milan and their irate supporters have left the door open for his return.
Indeed, the Rossoneri have actually handled the affair masterfully, diplomatically and sensitively. New CEO Marco Fassone and sporting director Massimiliano Mirabelli have become instant heroes in the eyes of the fans for the way in which they have stood up to a man considered as a bully.
Raiola, by contrast, has made one mistep after another. He usually retains the unwavering loyalty of his clients but it is worth noting that he doesn't always get his own way.
Back in 2012, Raiola tried to push his then client Marek Hamsik to leave Napoli. The player decided otherwise, though, explaining that he wanted to become a legend at the San Paolo.
As a result, he stayed with Napoli but left Raiola, with the Slovak explaining, "In Naples, I am part of community, a family that holds a very special place in my heart."
The hope now is that Donnarumma reaches a similar conclusion.
Before Italy's clash with Germany in Poland, the Milan fans in attendance unfurled a banner which read, "If you have Milan in your heart, leave your agent." It is the best piece of advice he has been given in some time.