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Transactions with Related Persons	12 Months Ended
Transactions with Related Persons	Dec. 31, 2018
Related Party Transactions [Abstract]
Transactions with Related Persons	Transactions with Related Persons During 2017, the Company repurchased shares from Franklin Mutual Advisers, a beneficial owner of the Company. On July 13, 2017, the Company repurchased 235,000 White Mountains common shares for $850.00 per share, the market price at the time the agreement was reached. During 2016, the Company repurchased shares from Franklin Mutual Advisers in two transactions. On April 19, 2016, the Company repurchased 325,000 White Mountains common shares for $807.00 per share, the market price at the time the agreement was reached. On September 15, 2016, the Company repurchased 305,000 White Mountains common shares for $820.00 per share, the market price at the time the agreement was reached.