Massachusetts Mutual Life Insurance Company Announces Results for Private Exchange Offers for Any and All of Its Outstanding 5⅝% Surplus Notes due 2033, 8⅞% Surplus Notes due 2039, 5⅜% Surplus Notes due 2041 and 4½% Surplus Notes due 2065

SPRINGFIELD, Mass., Oct. 9, 2019 /PRNewswire/ -- Massachusetts Mutual Life Insurance Company ("MassMutual") today announced the results of its previously announced four separate exchange offers (each an "Exchange Offer" and, collectively, the "Exchange Offers") for any and all of its outstanding 5⅝% Surplus Notes due 2033 (the "2033 Surplus Notes"), 8⅞% Surplus Notes due 2039 (the "2039 Surplus Notes"), 5⅜% Surplus Notes due 2041 (the "2041 Surplus Notes") and 4½% Surplus Notes due 2065 (the "2065 Surplus Notes" and, together with the 2033 Surplus Notes, the 2039 Surplus Notes and the 2041 Surplus Notes, the "Tendered Surplus Notes") held by Eligible Holders (as defined below). The Tendered Surplus Notes are being exchanged for consideration consisting of MassMutual's 3.729% Surplus Notes due 2070 (the "New Surplus Notes") and, if applicable, cash equal to the applicable Exchange Consideration (as defined in the Offering Memorandum (as defined below)).

As of the expiration time of 5:00 p.m., New York City time, on October 8, 2019 (the "Expiration Time"), according to information provided by D.F. King & Co., Inc., the information and exchange agent for the Exchange Offers, $56,816,000 aggregate principal amount of the 2033 Surplus Notes (or approximately 22.73% of the outstanding principal amount of the 2033 Surplus Notes), $180,403,000 aggregate principal amount of the 2039 Surplus Notes (or approximately 58.19% of the outstanding principal amount of the 2039 Surplus Notes), $136,276,000 aggregate principal amount of the 2041 Surplus Notes (exclusive of $5,352,000 aggregate principal amount of the 2041 Surplus Notes expected to be tendered pursuant to the guaranteed delivery procedures set forth in the Offering Memorandum) (or approximately 34.07% of the outstanding principal amount of the 2041 Surplus Notes) and $241,788,000 aggregate principal amount of the 2065 Surplus Notes (exclusive of $157,000 aggregate principal amount of the 2065 Surplus Notes expected to be tendered pursuant to the guaranteed delivery procedures set forth in the Offering Memorandum) (or approximately 48.36% of the outstanding principal amount of the 2065 Surplus Notes) was validly tendered and not validly withdrawn in the Exchange Offers (including Tendered Surplus Notes expected to be tendered pursuant to the guaranteed delivery procedures set forth in the Offering Memorandum).

MassMutual expects to accept for exchange on the Settlement Date (as defined below) all of the Tendered Surplus Notes that were validly tendered and not validly withdrawn in the Exchange Offers as described above (including Tendered Surplus Notes expected to be tendered pursuant to the guaranteed delivery procedures set forth in the Offering Memorandum).

The settlement date will be promptly following the Expiration Time and is expected to be October 11, 2019 (the "Settlement Date"). Tendered Surplus Notes validly tendered pursuant to the guaranteed delivery procedures set forth in the Exchange Offer Materials and accepted for exchange by MassMutual in any Exchange Offer are expected to settle on the Settlement Date.

Based on the aggregate principal amount of Tendered Surplus Notes validly tendered and not validly withdrawn in the Exchange Offers, and the applicable Exchange Consideration for each series of Tendered Surplus Notes, MassMutual expects to issue up to $837,977,000 aggregate principal amount of New Surplus Notes and pay approximately $39,146,437 in cash in exchange for such Tendered Surplus Notes on the Settlement Date (plus accrued and unpaid interest in respect of such Tendered Surplus Notes to but excluding the Settlement Date). As a result, the condition to the Exchange Offers that at least $300,000,000 aggregate principal amount of New Surplus Notes be validly issued in connection with the Exchange Offers is expected to be met.

The Exchange Offers were made solely to Eligible Holders upon the terms and subject to the conditions set forth in the confidential offering memorandum (as it may be amended or supplemented from time to time, the "Offering Memorandum"), and the related notice of guaranteed delivery (as it may be amended or supplemented from time to time, the "Notice of Guaranteed Delivery", and collectively with the Offering Memorandum, the "Exchange Offer Materials"), each dated October 2, 2019.

The Exchange Offers were made, and the New Surplus Notes will be offered and issued, only (i) in the United States, to holders of Tendered Surplus Notes who are "qualified institutional buyers," as defined in Rule 144A under the Securities Act of 1933, as amended (the "Securities Act"), (ii) to a limited number of institutional "accredited investors" within the meaning of Rule 501(a)(1), (2), (3) or (7) under the Securities Act, and (iii) outside the United States, to holders of Tendered Surplus Notes who are not "U.S. persons," as defined in Rule 902 under the Securities Act in reliance on Regulation S under the Securities Act. MassMutual refers to the holders of Tendered Surplus Notes who have certified that they are eligible to participate in any of the Exchange Offers pursuant to at least one of the foregoing conditions as "Eligible Holders."

This press release is for informational purposes only and is neither an offer to purchase nor a solicitation of an offer to sell any securities. The Exchange Offers were made and the New Surplus Notes were offered only to Eligible Holders. The New Surplus Notes have not been registered under the Securities Act or under any state or foreign securities laws, and may not be offered or sold in the United States absent registration or an applicable exemption from the registration requirements of the Securities Act, and, accordingly, are subject to significant restrictions on transfer and resale as more fully described in the Exchange Offer Materials. The Exchange Offers are subject to the terms and conditions set forth in the Exchange Offer Materials.

Forward-Looking Statements

This press release may contain "forward-looking statements." Forward-looking statements are those not based on historical information, but rather, relate to future operations, strategies, financial results or other developments, and contain terms such as "may," "expects," "should," "believes," "anticipates," "intends," "estimates," "projects," "goals," "objectives" or similar expressions. Forward-looking statements are based upon estimates and assumptions. These statements may change due to business uncertainties, economic uncertainties, competitive uncertainties, and other factors, many of which are beyond MassMutual's control. Additionally, MassMutual's business decisions are also subject to change. MassMutual does not publicly update or revise any forward-looking statements as a result of new information, future developments or otherwise except as may be required by law. Forward-looking statements are not guarantees of future performance and involve risks and uncertainties and actual results may differ materially from those in the forward-looking statements as a result of various factors.

About MassMutual

MassMutual is a leading mutual life insurance company that is run for the benefit of its members and participating policyowners. MassMutual offers a wide range of financial products and services, including life insurance, disability income insurance, long term care insurance, annuities, retirement plans and other employee benefits. For more information, visit www.MassMutual.com.

Contact: Tom Long, 212-269-5550, tlong@dfking.com

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