X0306 4 2022-03-22 0 0000075208 OVERSEAS SHIPHOLDING GROUP INC OSG 0001712582 Trueblood Richard C/O OVERSEAS SHIPHOLDING GROUP, INC. 302 KNIGHTS RUN AVE, SUITE 1200 TAMPA FL 33602 0 1 0 0 VP & CFO Class A Common Stock 2022-03-22 4 M 0 17809 0.00 A 158784 D Class A Common Stock 2022-03-22 4 F 0 4337 2.10 D 154447 D Class A Common Stock 2022-03-23 4 M 0 30773 0.00 A 185220 D Class A Common Stock 2022-03-23 4 F 0 7494 2.10 D 177726 D Class A Common Stock 2022-03-23 4 M 0 18008 0.00 A 195734 D Class A Common Stock 2022-03-23 4 F 0 4385 2.10 D 191349 D Restricted Stock Units 2022-03-22 4 M 0 17809 0.00 D Class A Common Stock 17809 0 D Restricted Stock Units 2022-03-23 4 M 0 30773 0.00 D Class A Common Stock 30773 30773 D Restricted Stock Units 2022-03-23 4 M 0 18008 0.00 D Class A Common Stock 18008 36017 D Restricted Stock Units 2022-03-24 4 A 0 77751 0.00 A Class A Common Stock 77751 77751 D Performance Restricted Stock Units 2022-03-24 4 A 0 38876 0.00 A Class A Common Stock 38876 38876 D Performance Restricted Stock Units 2022-03-24 4 A 0 38876 0.00 A Class A Common Stock 38876 38876 D Performance Restricted Stock Units 2022-03-24 4 A 0 46077 0.00 A Class A Common Stock 46077 46077 D Represents vesting of final installment of restricted stock units granted on March 22, 2019 pursuant to the Overseas Shipholding Group, Inc. Management Incentive Compensation Plan. The units vest as to one-third of the units granted on the first, second and third anniversaries of the date of grant. Each unit represents the right to acquire one share of OSG Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion Represents shares of Class A Common Stock withheld by the registrant in payment of the reporting person's tax withholding liability incurred as a result of the vesting the Restricted Stock Units. Represents vesting of an installment of restricted stock units granted on March 23, 2020 pursuant to the Overseas Shipholding Group, Inc. 2019 Incentive Compensation Plan for Management. The units vest as to one-third of such units on the first, second and third anniversaries of the date of grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. Represents vesting of an installment of restricted stock units granted on March 23, 2021 pursuant to the Overseas Shipholding Group, Inc. 2019 Incentive Compensation Plan for Management. The units vest as to one-third of such units on the first, second and third anniversaries of the date of grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. These restricted stock units were granted on March 22, 2019 pursuant to the Overseas Shipholding Group, Inc. Management Incentive Compensation Plan and vest as to one third of such units on each of the first, second and the third anniversaries of the date of the grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. These restricted stock units were granted on March 23, 2020 pursuant to the Overseas Shipholding Group, Inc. 2019 Incentive Compensation Plan for Management and vest as to one third of such units on each of the first, second and the third anniversaries of the date of grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. These restricted stock units were granted on March 23, 2021 pursuant to the Overseas Shipholding Group, Inc. 2019 Incentive Compensation Plan for Management and vest as to one third of such units on each of the first, second and the third anniversaries of the date of grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. These restricted stock units were granted on March 24, 2022 pursuant to the Overseas Shipholding Group, Inc. 2019 Incentive Compensation Plan for Management and vest as to one third of such units on each of the first, second and the third anniversaries of the date of grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. These restricted stock units were granted on March 24, 2022 pursuant to the 2019 Incentive Compensation Plan for Management and vest on December 31, 2024 (the end of the three-year performance period). Each unit represents the right to acquire one share of Class A Common Stock, subject to the satisfaction of the applicable performance goal. Settlement of the vested units may be in either shares of Class A Common Stock or cash, as determined by the Committee in its discretion. These restricted stock units were granted on March 24, 2022 pursuant to the Overseas Shipholding Group, Inc. 2019 Incentive Compensation Plan for Management and vest 20% of the units granted on the first anniversay, 30% on the second anniversary and 50% on the third anniversary, respectfully, of the date of grant. Each unit represents the right to acquire one share of Class A Common Stock. Settlement of vested units may be in either shares of Class A Common Stock or cash as determined by the Human Resources and Compensation Committee of the Board in its discretion. /s/ Richard Trueblood 2022-03-24