 By March 1865 , the Confederate military situation was desperate . Most major population centers had fallen , and General Lee 's defense of Richmond was faltering against massive Union forces . Nevertheless , Benjamin retained his usual good humor ; on the evening of April 1 , with evacuation likely , he was at the State Department offices , singing a silly ballad of his own composition , " The Exit from Shocko Hill " , a graveyard district located in Richmond . On April 2 , Lee sent word that he could only keep Union troops away from the line of the Richmond and Danville Railroad for a short time . Those who did not leave Richmond would be trapped . At 11 : 00 pm that night , the Confederate President and Cabinet left aboard a Danville @-@ bound train . Navy Secretary Stephen R. Mallory recorded that Benjamin 's " hope and good humor [ was ] inexhaustible ... with a ' never @-@ give @-@ up @-@ the @-@ ship ' sort of air , referred to other great national causes which had been redeemed from far gloomier reverses than ours " . 
