First, he started a storm by recruiting controversial ex-Cardiff City manager Malky Mackay.
Now Wigan Athletic owner Dave Whelan has himself become the subject of a Football Association (FA) investigation after making offensive comments while defending his choice of Mackay as manager of the Championship club.
Mackay, 42, is under investigation by the FA after supposedly exchanging offensive messages with Cardiff City's ex-head of recruitment Iain Moody.
In one of the messages, Mackay allegedly described Cardiff City owner Vincent Tan as a "chink".
In another, he said of Jewish agent Phil Smith: "Nothing like a Jew that sees money slipping through his fingers."
Mackay said in a third text message that there were "enough dogs in Cardiff to go round" after signing South Korean international Kim Bo Kyung.
Multimillionaire Whelan, 77, told The Guardian newspaper that he felt that Mackay's comments were not offensive.
Mr Whelan reportedly said he used the word "chink" when he was young. "If any Englishman said he has never called a Chinaman a chink, he is lying," he said.
He added: 'The Jews don't like losing money. Nobody likes losing money. Do you think Jewish people chase money a little bit more than we do?
"It's telling the truth. Jewish people love money, English people love money - we all love money.
Mr Whelan later apologised for his remarks, saying that he has "hundreds of Jewish friends".
He told Sky News: "I have loads of Chinese friends and I would never, ever insult the Chinese."
But his apology has been rejected by the Board of Deputies of British Jews, which acts as the main representative body of Jews in Britain.
It said the apology was "half-hearted", adding that the comments were "outrageous and offensive".
The board also accused him of bringing Wigan Athletic and the game into disrepute and that it would be taking up the issue with the FA.
One of Wigan's shirt sponsors, Premier Range, had severed ties with the club due to the decision to appoint Mackay. Another commercial partner, drinks supplier iPro Sport, has also cut its links with the club.
This article was first published on Nov 22, 2014. Get The New Paper for more stories.