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Transactions with related parties
6 Months Ended
Jun. 30, 2020
Related Party Transactions [Abstract]  
Transactions with related parties
Transactions with related parties
(Re)insurance contracts
In the normal course of business, Sirius Group enters into insurance and reinsurance contracts with certain of its insurance and MGU affiliates, or their subsidiaries. During the three and six months ended June 30, 2020, these contracts resulted in gross written premiums of $26.8 million and $68.1 million, respectively. During the three and six months ended June 30, 2019, these contracts resulted in gross written premiums of $24.9 million and $49.0 million, respectively. As of June 30, 2020 and December 31, 2019, Sirius Group had total receivables due from affiliates of $31.6 million and $16.1 million, respectively. As of both June 30, 2020 and December 31, 2019, Sirius Group had total payables due to affiliates of $0.9 million.

Transaction Matters Letter Agreement

On August 10, 2020, the Company paid $1.9 million for certain legal expenses incurred by CM Bermuda Limited ("CM Bermuda"), a Bermuda exempted company and majority shareholder of Sirius Group and CMIG International Holding Pte. Ltd. (“CMIG International”) in connection with the Transaction Matters Letter Agreement entered into by Sirius Group, CM Bermuda and CMIG International on August 6, 2020. (See Note 20.)

Series B preference shareholders expense reimbursement agreement

On March 27, 2020, the Company entered into an expense reimbursement agreement (the “Agreement”) with each of the holders of the Series B preference shares. Pursuant to the Agreement, the Company agreed to reimburse each of the holders of the Series B preference shares for all reasonable and documented out-of-pocket expenses incurred by them in connection with pursuing a potential negotiated transaction (a “Potential Transaction”) involving the Company or one or more of its subsidiaries on or after January 8, 2020 up to $250,000 for each holder of Series B preference shares together with its affiliates and $1,000,000 in the aggregate with any reimbursement above such amounts requiring the written consent of the Company (but excluding any expenses incurred in connection with the evaluation or enforcement of any rights or obligations of the holders of the Series B preference shares or the Company relating to the preference shares in the Company held by such Series B preference shareholders). In addition, the Company agreed to reimburse the holders of the Series B preference shares for any and all reasonable and documented out-of-pocket attorneys’ fees or other fees payable to third party advisors up to $500,000 in the aggregate to the extent arising out of any litigation, dispute, arbitration or other proceeding commencing after the date of the Agreement that is not brought or commenced by a holder of the Series B preference shares and involves the Company, such Series B preference shareholder's investment in the Company or a Potential Transaction. As of the end of the second quarter 2020, no payments have been requested or made under the Agreement.
Other
Meyer "Sandy" Frucher is the Company's Chairman of the Board of Directors and was also Vice Chairman of Nasdaq, Inc. ("Nasdaq") until December 2019. On January 1, 2020, Mr. Frucher concluded his tenure as Vice Chairman of Nasdaq and assumed the role of Strategic Advisor to Nasdaq. The Company is traded on the Nasdaq Global Select Market and has business transactions that are related to its listing on the exchange under the normal course of business. (See Note 3.)