TORONTO – An Ontario Superior Court judge has ordered a Toronto businessman to pay more than $6.1 million in damages, interest, and costs to a pair of real estate investors after a deal to purchase a North York office building fell apart amid a campaign of harassment and financial manoeuvres1. The decision, released on September 8, 2025, concludes a decade long legal battle over the property at 240 Duncan Mill Road. Justice Leiper granted a default judgment in favour of Jamshid Hussaini, Neelofar Ahmadi, and their company, Homelife Dreams Realty Inc., against Alain Checroune, the building’s former owner.
The complex dispute originated in 2012 when Hussaini and Ahmadi entered into a share purchase agreement with Checroune. The agreement was structured for the plaintiffs to acquire Checroune’s company, 1482241 Ontario Ltd., which held the Duncan Mill property as its sole major asset. The total purchase price for the shares was set at $15 million. As a first step, the plaintiffs paid Checroune a deposit of $1.2 million, which secured them a 20% stake in the corporation. Under the terms of the deal, the transaction’s closing, scheduled for October 1, 2015, was conditional on Checroune fulfilling a crucial obligation: he was required to use his best efforts to provide clear title to the property by discharging a Certificate of Pending Litigation that was registered against it. Once the title was cleared, Hussaini and Ahmadi were to pay the remaining $4.8 million for the other 80% of the shares and arrange financing to pay off the building’s existing mortgage.
As part of their vision for the property, the agreement also allowed Hussaini and Ahmadi to lease the sixth floor of the building. Their plan was to operate their own business from the space and build a profitable business centre by subletting the remaining units to other tenants. They invested significantly in leasehold improvements to realize this goal, proceeding with the understanding that they would soon be the full owners of the building. However, the closing date of October 1, 2015, came and went without the transaction being completed. According to the court’s findings, Checroune not only failed to close the deal but actively began to undermine the plaintiffs’ interests in the property.
Justice Leiper’s decision details a prolonged and disturbing course of conduct by Checroune following the failed closing. The evidence presented to the court showed that he began interfering with the plaintiffs’ tenancy and the operations of their sub tenants on the sixth floor. He also made attempts to sell the Duncan Mill property to other potential buyers, contrary to his agreement with Hussaini and Ahmadi. In a direct threat, Checroune told one of the plaintiffs that he would deliberately encumber the property with new mortgages to trigger power of sale proceedings, a move that would effectively wipe out their contractual interest in the building.
The plaintiffs initially responded by filing a lawsuit seeking specific performance, a legal remedy that would have forced Checroune to complete the sale as agreed. As the litigation commenced, Checroune’s behaviour escalated. He took tangible steps to make good on his threats, placing additional mortgages on the property. His actions against the tenants on the sixth floor grew more aggressive. The court heard evidence that Checroune engaged in a pattern of harassment that included pulling a knife on a sub tenant, an act for which he was criminally charged. He also locked out sub tenants, shut down the building without notice, issued fraudulent parking tickets, failed to maintain the elevators in working order, turned off the lights during business hours, and cut off the air conditioning. In a further effort to dismantle the plaintiffs’ business centre, Checroune approached their sub tenants with offers of lower rent if they would relocate to different floors within the same building, directly interfering with the plaintiffs’ economic rights.
The legal battle saw several turns. In 2017, Checroune brought an unsuccessful motion for summary judgment to have the plaintiffs’ case dismissed. Following this, he took the drastic step of putting his corporation into bankruptcy. This action proved to be the final blow to the plaintiffs’ hope of ever owning the building. The Trustee in Bankruptcy took control of the property and, on March 29, 2018, sold it for $19 million. The proceeds from the sale were distributed to the corporation’s creditors, but the plaintiffs received no funds from the sale, nor did they receive the remaining 80% of the shares they had contracted to buy. Their primary legal remedy of specific performance was now rendered meaningless.
The litigation continued for several more years, though Checroune’s participation waned significantly after 2019. His ongoing failure to comply with court orders culminated in a motion before Associate Justice La Horey on July 19, 2024. Checroune did not attend the hearing, and the Associate Justice ordered his pleadings struck from the record, noting him in default. This paved the way for the plaintiffs to move for a default judgment, which was heard in writing by Justice Leiper. Since Checroune was in default, the court accepted the plaintiffs’ evidence as factually established.
In his final decision, Justice Leiper found that Checroune had unequivocally breached the share purchase agreement. The judge determined that Checroune failed to close the transaction when he was able to do so and instead engaged in a series of manoeuvres to frustrate the sale after receiving the $1.2 million deposit. Justice Leiper also noted that because Checroune had demonstrated a clear intention not to complete the deal, the plaintiffs were not required to formally tender their final payment. Checroune’s actions, including encumbering the property and harassing the tenants, made him personally liable for the resulting damages.
The judge awarded the plaintiffs damages on several grounds. First, he awarded $4 million for the lost opportunity, representing the difference between the $15 million contract price and the $19 million for which the building was ultimately sold by the bankruptcy trustee. Second, Justice Leiper ordered the return of the plaintiffs’ $1.2 million deposit. The court rejected Checroune’s earlier claim that he had applied the deposit to other alleged debts, finding that the share purchase agreement did not permit him to do so.
Furthermore, the court granted the plaintiffs an additional award under the oppression remedy provisions of Ontario’s Business Corporations Act. Justice Leiper found that Checroune’s conduct was oppressive and unfairly disregarded the plaintiffs’ interests as 20% shareholders. For these oppressive acts, the judge ordered compensation of $930,000, an amount which consisted of $130,000 for the value of lost leasehold improvements and $800,000 for lost rents from their sub tenants. The total damage and compensation award amounted to $6.13 million. The judge did decline to award two smaller amounts sought by the plaintiffs related to lost commission and a damage deposit allegedly paid under duress, stating the evidence for duress was insufficient.
To account for the significant passage of time, Justice Leiper ordered that prejudgment interest be applied to the entire award. He ruled that the interest should be calculated from October 1, 2015, the date the original transaction was supposed to close. The judge noted that Checroune’s course of conduct suggested he had no intention of completing the transaction when he signed the agreement and that he simply used the asset to extract a deposit from the plaintiffs. Finally, the court awarded the plaintiffs their legal costs for the lengthy litigation on a partial indemnity basis, ordering Checroune to pay an additional $230,312.52.
