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One "What if" that I like to think about is the question of "What if John Wilkes Booth had completed his plan of kidnapping Abraham Lincoln before he assassinated him?"
A Lincoln abduction has been a subject handled if several works of fiction so far such as an episode of "Voyagers!", the novel "Sahara", and the novel "Notes on My Recent Abduction by A. Lincoln".
According to the Wikipedia page on the Assassination of Abraham Lincoln Booth first conceived his plan to kidnap Lincoln in March 1864 after hearing that General Grant had ended POW exchanges and as stated on the Wikipedia page on John Wilkes Booth -
"He began to formulate plans to kidnap Lincoln from his summer residence at the Old Soldiers Home, three miles (5 km) from the White House, and to smuggle him across the Potomac River into Richmond. Once in Confederate hands, Lincoln would be exchanged for the release of Confederate Army prisoners of war held captive in Northern prisons and, Booth reasoned, bring the war to an end by emboldening opposition to the war in the North or forcing Union recognition of the Confederate government."
Also according to that page one the subject of Booth attempt at executing the kidnapping-
"On March 17, Booth learned that Lincoln would be attending a performance of the play Still Waters Run Deep at a hospital near the Soldier's Home. Booth assembled his team on a stretch of road near the Soldier's Home in the attempt to kidnap Lincoln en route to the hospital, but the president did not appear. Booth later learned that Lincoln had changed his plans at the last moment to attend a reception at the National Hotel in Washington where, coincidentally, Booth was then staying"
I'd like to make a special mention that the last fictional novel mentioned above, "Notes on My Recent Abduction by A. Lincoln", deal with Booth competing the kidnapping with in March, 1864.
So with this all stated I would like to ask what event would follow the abduction of Abraham Lincoln if he was then escorted into confederate lines any time between his first term and the end of the ACW during his second term? Would the actions taken by his cabinet be? Would his Vice president from whatever term involved immediately step in as acting president? If so what actions might they take and how well might those actions be completed? What requests could the CSA make with Lincoln as a hostage besides the release of POWs? What requests made by the CSA would the Union be likely to agree too? Etc.