Open this photo in gallery Ontario Minister Michael Tibollo watches one of the big screen televisions at the election night reception for Conservative MP Julian Fantino in Vaughan on Oct. 19, 2015. Peter Power

Ontario Minister of Community Safety and Correctional Services Michael Tibollo is mired in multiple ongoing lawsuits that include allegations of professional misconduct by his law firm and a failure to pay debts.

Legal records show the Conservative minister, who oversees policing regulations and the Ontario Provincial Police, or his law firm, have been defendants in five suits over the past four years.

Mr. Tibollo, 58, founded the law firm Tibollo & Associates Professional Corporation in Woodbridge, Ont., just north of Toronto.

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When asked for a response to the allegations in the lawsuits, Mr. Tibollo’s press secretary, Brett Weltman, did not address the legal actions, but said the minister has made all the personal disclosures that MPPs are required to make to the province’s Integrity Commissioner, David Wake, "who has expressed no concerns about the Minister’s file.”

A spokeswoman for the Law Society of Ontario said Mr. Tibollo has not been the subject of any disciplinary proceeding.

In April, 2016, Inktronic Technology Inc., a commercial printing firm, and its three principal owners filed a lawsuit against Mr. Tibollo and his firm claiming advice Mr. Tibollo provided caused it serious financial losses.

In its statement of claim, Inktronic said Mr. Tibollo acted for the company in a transaction to sell some of its assets to competitor. It alleges Mr. Tibollo failed to explain to Inktronic’s owners the terms of the contract for the transaction, which included restrictions on who they could conduct business with after the sale. Inktronic claims Mr. Tibollo failed in his duty to carry out its wishes and that he was using non-lawyers to do legal work on the file.

“Tibollo’s conduct in this regard was negligent and contravenes the Rules of Professional Conduct representing supervision of non-lawyer employees,” the statement of claim alleges.

The allegations have not been proven in court. In his statement of defence, Mr. Tibollo said Inktronic’s owners were “fully and completely aware of all terms of the relevant agreements referenced in the statement of claim.” Joseph Figliomeni, the lawyer acting for the plaintiffs, declined to comment.

Nina Deluca-Ford, an accountant, filed a lawsuit in 2016 against Mr. Tibollo and his wife, Silvana Tibollo, and Yonge St. Holdings, a company owned by Ms. Tibollo, for alleged non-payment of more than $108,000 in fees. Neither Ms. Deluca-Ford nor her lawyer could be reached for comment. Mr. Tibollo and his wife filed a counterclaim in which they say Ms. Deluca-Ford failed to invoice them properly for the work. They are seeking $70,000 in damages and are represented in the legal proceeding by Bhupinder Nagra, a lawyer at Tibollo & Associates.

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In addition to legal actions filed against Mr. Tibollo personally, his law firm has been sued twice as a result of allegations against Ms. Nagra and Barbara Romanow, a mortgage broker whose licence was suspended this summer by the Superintendent of Financial Services of Ontario.

One of these lawsuits was filed early this year by Ottawa home builder Jerzy Nowacki and his wife. They accused Ms. Nagra and Ms. Romanow of being part of a plan to defraud them of more than $10-million. The statement of claim, filed in Ontario Superior Court, alleged that Ms. Nagra and Ms. Romanow devised a “low risk” investment plan in which Mr. Nowacki would lend money to Ms. Romanow’s company for 30 days at a time and be repaid with interest. The lawsuit alleges she stopped repaying the funds after six months.

Mr. Nowacki said he expects the dispute to be resolved out of court.

Ms. Nagra and Ms. Romanow have not yet filed a statement of defence, but say the lawsuit is without merit.

“There is no truth to the allegations,” Ms. Nagra said in an interview. The firm’s only involvement in this transaction was “independent legal advice,” that Ms. Nagra said she provided to Ms. Romanow on one occasion about the terms of a contract related to the investment. “The written content in the Nowacki claim is extremely fabricated and the allegations of fraud are misleading and false,” Ms. Romanow said in an e-mail, adding that she intends to defend herself at an unrelated disciplinary proceeding regarding her mortgage brokers licence.

The Tibollo law firm and Ms. Nagra were also named in a 2015 lawsuit filed by one of Ms. Nagra’s clients who alleged she persuaded him to lend nearly $50,000 to Ms. Romanow and it was not repaid. The lawsuit was settled out of court and the terms are confidential.

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Ms. Nagra said that once the claim was filed, she ensured the plaintiff was re-paid. Ms. Romanow called the outcome “very positive."

Mr. Tibollo is also facing a defamation suit. Mario Sergio, who retired as a Liberal MPP this year, is seeking damages from Mr. Tibollo and the publisher of Panoram Italia Magazine. The lawsuit alleges that Mr. Tibollo paid for an “advertorial” in the magazine this year in which he claimed to have been “instrumental” in the enactment of legislation in 2010 that proclaimed June as Italian heritage month. The former Liberal MPP’s statement of claim says that Mr. Sergio actually introduced the bill and worked to pass it, and that the ad damages his reputation and legacy. Ms. Nagra is representing Mr. Tibollo and she indicated a statement of defence is about to be filed.

Mr. Tibollo also faced an earlier legal action related to real estate transactions with two business partners, including the purchase of properties near the GO Station in Brampton, Ont.

Baywood Golf Developments Inc. sued Mr. Tibollo and two other people in 2008 for the alleged failure to repay $1.25-million in loans to cover mortgage payments on five of those properties in Brampton. The company sought a requisition for “writ of seizure and sale” of the properties in 2011 as a result of the failure to comply with a Superior Court order to repay the funds. The case is still before the courts.

Land records show that Mr. Tibollo and the two business partners later sold these properties to the provincial transporation agency Metrolinx as part of a planned expansion of its GO Station in Brampton. A spokeswoman for Metrolinx said it would not make public the terms of the sale. It is not required to do so as a Crown agency to protect future real estate deals.

Ownership of six other properties in that same section of Brampton was transferred from Mr. Tibollo and his business partners through a power of sale in 2012, according to land records.

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In 2006, Mr. Tibollo was acquitted of securities act charges by an Ontario Securities Commission panel in connection with a stock fraud case. The OSC hearing stemmed from allegations related to Sussex International, a Barbados-registered company headed by Mr. Tibollo in the late 1990s that was formed to consolidate business operations in Cuba for an initial public offering. The OSC accused the company of accepting investments contrary to securities act regulations. The panel found that it could not conclude Mr. Tibollo engaged in illegal trading or unregistered distributions of shares in that company or Saxton Securities, a related firm. Mark Allan Eizenga, the president of Saxton, was sentenced to eight-years in prison and ordered to pay back more than $20-million to defrauded investors.

However, the OSC panel indicated disapproval of Mr. Tibollo’s conduct. “Although we determined that he did not solicit the sale of Saxton or Sussex International securities, he, as the president of Sussex Group from November, 1997, until 2000, knew by virtue of his meetings with two lawyers in the summer of 1997, about the illegality of the sales of Saxton securities and that Eizenga had not complied with securities law in raising funds that were used for the Cuban operations,” the panel stated.

With reports from Stephanie Chambers