A member of the Republican political machine in post-Civil War Washington, D.C., Cooke was appointed first territorial governor of the District of Columbia by Ulysses S. Grant.

Consul W. G. Moorhead told other State Department officials about the idea, and in about two years the Pacific Mail Steamship Company was organized.

Although it was unprofitable, it made him a favorite of various Washington officials, including Treasury Secretary Salmon P. Chase, Senator John J. Sherman, and General Ulysses S. Grant.

Sherman's position on the Commission of Ways and Means allowed Henry Cooke to gain a profitable contract for government binding, and in 1862 helped to make him president of the Washington and Georgetown Street Railroad Company.

In 1870, the national capital was in dire financial straits, with both Congress and local government more involved with racial integration and civil rights policies for former slaves than with fiscal solvency or basic city services.

[4] Congress passed the bill in January 1871, and in the following month, President Ulysses S. Grant made Cooke, his friend (and an ally of Shepherd), governor of the District.

This move undercapitalized the company, such that it took out several unsecured loans to fund its operations, notably from the Freedman's Savings Bank, which served freed African-American slaves and their descendants.

Henry Cooke sat on the boards of both the Seneca Sandstone Company and the Freedman's Bank and facilitated the loans, though this was a clear conflict of interest.