When false expectations of the ultimate triumph of Secession led him to cast his lot with the Southern Confederacy, he did not solicit a command in the field, but took up his quarters in Richmond, to become a sort of Informer-General, High-Inquisitor and Chief Eavesdropper for his intimate friend, Jefferson Davis.

He pried and spied around into every man's bedroom and family circle, to discover traces of Union sentiment.

The wildest tales malice and vindictiveness could concoct found welcome reception in his ears.
He was only too willing to believe, that he might find excuse for harrying and persecuting.

He arrested, insulted, imprisoned, banished, and shot people, until the patience even of the citizens of Richmond gave way, and pressure was brought upon Jefferson Davis to secure the suppression of his satellite.

For a long while Davis resisted, but at last yielded, and transferred Winder to the office of Commissary General of Prisoners.