X0306 4 2020-07-31 0 0000355379 MIDWEST HOLDING INC. MDWT 0001281933 BRATTON DOUGLAS K 201 MAIN STREET, SUITE 1900 FORT WORTH TX 76102 1 0 1 0 0001810802 CRESTLINE ASSURANCE HOLDINGS LLC 201 MAIN STREET, SUITE 1900 FORT WORTH TX 76102 1 0 1 0 0001536054 Crestline Management, LP 201 MAIN STREET, SUITE 1900 FORT WORTH TX 76102 1 0 1 0 0001626596 Crestline Investors, Inc. 201 MAIN STREET, SUITE 1900 FORT WORTH TX 76102 1 0 1 0 Stock Option (right to buy) 0.05 2020-07-31 4 A 0 50000 0.00 A 2020-07-31 Voting Common Stock 50000 50000 I See Footnotes Non-Qualified Stock Options granted under the Midwest Holding Inc. 2019 Long-Term Incentive Plan to Douglas K. Bratton for his service on the Board of Directors (the "Board") of Midwest Holding Inc. (the "Issuer"). The Non-Qualified Stock Options vest as follows: (i) 25,000 Options shall vest on July 31, 2022; and (ii) 25,000 Options shall vest on July 31, 2024, in each case subject to Mr. Bratton's continued service on the Issuer's Board. Mr. Bratton serves on the Issuer's Board as a representative of Crestline Assurance Holdings LLC ("Crestline Assurance") and its affiliates. Mr. Bratton holds the Options reported herein for the benefit of Crestline Assurance and as a result does not have any direct pecuniary interest in such Options. Mr. Bratton may be deemed to have an indirect pecuniary interest in a portion of the Options through indirect membership interests in Crestline Assurance. The Manager of Crestline Assurance is Mr. Bratton and the Sole Member of Crestline Assurance is Crestline Management, L.P. ("Crestline Management"). Crestline Investors, Inc. ("Crestline") is the general partner of Crestline Management. Mr. Bratton is the sole director of Crestline. Crestline Management, Crestline and Mr. Bratton may each be deemed to beneficially own the securities beneficially owned by Crestline Assurance. (Continued from Footnote 2) Each such entity and Mr. Bratton disclaims beneficial ownership of such securities except to the extent of its or his respective pecuniary interest therein. Douglas K. Bratton is a member of the Board of Directors of Midwest Holding Inc. (the "Issuer"). For purposes of Section 16 of the Securities Exchange Act of 1934, as amended, Crestline Assurance Holdings LLC, Crestline Management, L.P. and Crestline Investors, Inc. may be deemed to be directors by deputization of the Issuer due to their relationship with Mr. Bratton. DOUGLAS K. BRATTON, /s/ Douglas K. Bratton 2020-08-04 CRESTLINE ASSURANCE HOLDINGS LLC, /s/ Douglas K. Bratton, Title: Manager 2020-08-04 CRESTLINE MANAGEMENT, L.P., By: Crestline Investors, Inc., its general partner, /s/ Douglas K. Bratton, Title: Sole Director 2020-08-04 CRESTLINE INVESTORS, INC., /s/ Douglas K. Bratton, Title: Sole Director 2020-08-04