WHITE MOUNTAINS INSURANCE GROUP LTD WTM

election_required = True...All Of My Shares, Will I Be Subject To Proration? If you own beneficially or of record fewer than 100 Shares in the aggregate, properly tender all of your Shares at or below the Purchase Price and do not properly withdraw them before the Expiration Time, and complete the section entitled Odd Lots in the Letter of Transmittal and, if applicable, in the Notice of Guaranteed Delivery, we will purchase all of your Shares without subjecting them to the proration procedure. See “Section 1. Number of Shares; Proration”. Do You Have The Financial Resources To Make Payment? Assuming that the Offer is fully subscribed and assuming we do not exercise the right to purch...

expiry = 2022-09-20...TO $500 MILLION IN VALUE OF ITS COMMON SHARES (CUSIP NUMBER G9618E107) AT A PURCHASE PRICE NOT GREATER THAN $1,400 NOR LESS THAN $1,250 PER SHARE ​ ​ THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON SEPTEMBER 20, 2022, UNLESS THE OFFER IS EXTENDED (SUCH TIME, AS IT MAY BE EXTENDED, THE “EXPIRATION TIME”). ​ ​ White Mountains Insurance Group, Ltd., a company organized under the laws of Bermuda (the “Company”, “White Mountains”, “we” or “us”), is offering...

expiry = 2022-09-20...d August 22, 2022 of up to $500 million in value of its Common Shares at a Purchase Price not greater than $1,400 nor less than $1,250 per share. ​ ​ THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON SEPTEMBER 20, 2022, UNLESS THE OFFER IS EXTENDED (SUCH TIME, AS IT MAY BE EXTENDED, THE “EXPIRATION TIME”). ​ ​ The Depositary for the Offer is: Computershare Trust Company, N.A. ​ By First Class, Registered or Certified Mail: Computershare Trust Company, N....

listed = True...ON”. TABLE OF CONTENTS This Offer is not conditioned upon the receipt of financing or any minimum number of Shares being tendered. This Offer is, however, subject to certain other conditions. See “Section 8. Conditions to the Offer”. The Shares are listed and traded on the New York Stock Exchange (the “NYSE”) under the symbol “WTM” and the Bermuda Stock Exchange under the symbol “WTM-BH”. On August 19, 2022, the last full trading day before the public announcement of the Offer, the last reported sale price of the Shares on the NYSE was $1,305.13 per Share. SHAREHOLDERS ARE URGED TO OBTAIN A CURRENT MARKET QUOTATION FOR THE SHARES. See “Sect...

mechanism = DUTCH...certain other conditions. See “Section 1. Number of Shares; Proration” and “Section 8. Conditions to the Offer”. ii TABLE OF CONTENTS How Much Are You Offering To Pay And What Is The Form Of Payment? We are conducting this Offer through a procedure called a “modified Dutch auction”. This procedure allows you to select the price (in increments of $1.00) within the price range specified by us at which you are willing to sell your Shares. The price range for the Offer is $1,250 to $1,400 per Share. See “Section 1. Number of Shares; Proration”. We will select the lowest purchase price per Share (in increments of $1.00...

must_tender_all = True...w) are properly tendered at or below the Purchase Price and not properly withdrawn, we will accept Shares for purchase in the following order of priority: • First, we will purchase all “odd lots” of less than 100 Shares at the Purchase Price from shareholders who properly tender all of their Shares at or below the Purchase Price and who do not properly withdraw them before the Expiration Time; and ​ • Second, after purchasing all the “odd lots” that were properly tendered at or below the Purchase Price, we will purchase Shares at the Purchase Price from all other holders who properly tender Shares at or below the Purchase Price and...

price = USD 1250.0-1400.0...ied Dutch auction”. This procedure allows you to select the price (in increments of $1.00) within the price range specified by us at which you are willing to sell your Shares. The price range for the Offer is $1,250 to $1,400 per Share. See “Section 1. Number of Shares; Proration”. We will select the lowest purchase price per Share (in increments of $1.00) (the “Purchase Price”) that will allow us to purchase up to $500 million in value of S...

threshold = 100...alue as we may elect to purchase, subject to applicable law). ​ Therefore, we may not purchase all of the Shares that you tender even if you tender them at or below the Purchase Price. Odd Lots. The term “odd lots” means all Shares tendered by any person (an “Odd Lot Holder”) who owned beneficially or of record a total of fewer than 100 Shares and so certified in the appropriate place on the Letter of Transmittal and, if applicable, on the Notice of Guaranteed Delivery. To qualify for the odd lot preference, an odd lot holder must tender all Shares owned in accordance with the procedures described in Section 4. Odd lots will be accepted for payment before any proration of the...

threshold = 100...rust company, or other nominee that (a) is tendering for the beneficial owner(s), Shares with respect to which it is the record holder, and (b) believes, based upon representations made to it by the beneficial owner(s), that each such person is the beneficial owner of an aggregate of fewer than 100 Shares and is tendering all such Shares. ​ In addition, the undersigned is tendering all such Shares either (check one box): ☐ at the Purchase Price, as the same will be determined by the Company in accordance with the terms of the Offer (persons checking this box should not check any box in the section captioned “Price (in Dollars) per Share a...

txn_type = TENDER_OFFEREX-99.A1A 2 tm2223096d1_ex99-a1a.htm EX-99.A1A tm2223096-1_sctoi_DIV_099-exhibitsa1a - none - 5.7812644s TABLE OF CONTENTS Exhibit (a)(1)(A)​ OFFER TO PURCHASE FOR CASH BY WHITE MOUNTAINS INSURANCE GROUP, LTD. OF UP TO $500 MILLION IN VALUE OF ITS COMMON SHARES (CUSIP NUMBER G9618E107) AT A PURCHASE PRICE NOT GREATER THAN $1,400 NOR LESS THAN $1,250 PER SHARE ​ ​ THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON SEPTEMB...

txn_type = TENDER_OFFER...9-a1j.htm EXHIBIT 99.(A)(1)(J) tm2223096-10_sctoia_DIV_100-exhibita1j - none - 3.7656264s ​ Exhibit (a)(1)(J)​ AMENDED AND RESTATED LETTER OF TRANSMITTAL To Tender Common Shares (CUSIP Number G9618E107) of WHITE MOUNTAINS INSURANCE GROUP, LTD. Pursuant to the Offer to Purchase Dated August 22, 2022 of up to $500 million in value of its Common Shares at a Purchase Price not greater than $1,400 nor less than $1,250 per share. ​ ​ THE OFFER, PRORATION PERIOD AND WITHDRAWAL RIGHTS WILL EXPIRE AT 12:00 MIDNIGHT, NEW YORK CITY TIME, AT THE END OF THE DAY ON SEPTEMBER 20, 2022, UNLESS THE OFFER IS EXTENDED (SUCH TIME...