The OSC settlement with Claire Drage
The investor money behind the companies' promissory notes was raised by Claire Drage and her companies. In December 2025 she admitted to fraud in a settlement with the Ontario Securities Commission.
Ms. Drage admitted to fraud under s.126.1(1)(b) of the Securities Act. From 2021 to 2024 about $285.8M was raised from investors across all of the borrowers. The Lion's Share itself owed about $89.5M to 447 lenders as at February 29, 2024, according to its receiver. Borrowers had little or no direct contact with investors; communications went through Ms. Drage and The Lion's Share.
The tribunal found that "Drage committed a large-scale fraud" and imposed permanent market bans. FSRA separately imposed $600,000 in penalties for a "prolonged and extensive pattern of misconduct".
No borrower company was a respondent, and no borrower is named in the settlement.
The other borrowers
The SID companies were one of a number of borrowers. The settlement describes the five largest. One advised Lion's Share that it intended to file a proposal under the Bankruptcy and Insolvency Act. One had difficulty refinancing projects that were overleveraged. One sold properties for less than the debt against them and "could not account for its use of all Investor funds received". The settlement adds: "In 2024, many of the Borrowers ceased making payments."
What investors were told, and by whom
The settlement records that the borrowers "had little to no communication with the Investors". Ms. Drage and The Lion's Share solicited investors and renewals with statements about the success of the businesses that were "false and misleading", and with assurances that Lion's Share and the borrowers were not and would not become overleveraged.
The Monitor's Fourth Report says investors expected the money they lent to go to the property named on their note.
The companies did not deal with the lenders directly. Windrose and Lion's Share prepared the notes and the marketing. The notes carried no restrictions on the use of funds.
Two kinds of notes
The settlement separates notes that Lion's Share issued in its own name, where investors lent to Lion's Share and it "then advanced loans to other corporations and individuals", from notes issued directly by borrowers, which Lion's Share brokered for a fee. On the first kind, the settlement records that Ms. Drage "Held herself out as the borrower for the Lion Share Notes".
Directors of the companies told the Monitor's counsel in April and May 2024 how they understood the Lion's Share notes. One said that on those notes "it was never told to us that it was anyone else's money aside from Lion's Share, who was Claire". Another said that Ms. Drage would tell them "I'm your biggest lender".
The unsecured debt figure
The Monitor reported that the $54.2M unsecured figure was "the amount initially provided by Ms. Drage" and that a reconciliation "has not been completed". In July 2026 it reported that the companies' creditor listings show obligations to Lion's Share of about $39.2M, without saying how much of that is mortgages and how much is notes; elsewhere it describes the Lion's Share claims as "both mortgage claims and promissory note claims". It said "the Claims Procedure will determine the quantum". A claims process limited to principal opened on July 30, 2026.
The unsecured notes reconcile to about $22.06M, not $54.2M; the stated figure is overstated by about $32M. In July 2026 the companies advised the Monitor that they believe the amount is "significantly less than the amount initially provided by Ms. Drage".
- The settlement records that all of the five largest borrowers had "numerous missed, deferred, late, or not-sufficient funds (NSF) payments" in 2021 to 2023, and that Lion's Share covered payments for at least four of them. The companies' position, citing the broker's own interview with the Monitor, is that they were generally current on all debt service through 2022, across about 390 first mortgages and 802 promissory notes. Motion Record of the Applicants (Jun 20, 2024), including the affidavit of Robert Clark, Exhibit O, items A.1, A.8 and B.11; OSC Settlement Agreement, Claire Drage et al. (Dec 16, 2025), para 25(ii) and (iii)
- It repeats the Monitor's concerns about the records of the largest borrower. OSC Settlement Agreement, Claire Drage et al. (Dec 16, 2025), para 25(xii)
- The settlement's facts are agreed for regulatory purposes only. It makes no finding that note balances were overstated or that any borrower overpaid. OSC Settlement Agreement, Claire Drage et al. (Dec 16, 2025), para 6
- The companies issued the promissory notes themselves. About 602 of about 802 were issued to Lion's Share. Pre-Filing Report of the Proposed Monitor (Jan 2024), s.3.2 para 1
- The $54,236,109.51 figure first appears in Mr. Clark's own affidavit of January 23, 2024, described there as based on the companies' books and records, which "may differ from those maintained by the Lenders". The companies' later evidence is that the figure reflected Windrose and Lion's Share records. Application Record, Vol. 1, including the first affidavit of Robert Clark (Jan 23, 2024), first affidavit, promissory notes table and note 6; Motion Record of the Applicants (Jun 20, 2024), including the affidavit of Robert Clark, Clark affidavit para 21