"If you want me, you had better send for me"

There was no central intelligence during the Civil War, just a hodgepodge of competing spook units. Every army had its own spy system, as did every city’s police force. Ciphers were an ancient spook technology, handed down in spook world for generations. Aaron Burr had been an early master of the art, trained by His Majesty’s Secret Service, but the South had no one like him and the Confederates lost the cipher war.

Tapping telegraph lines was a constant endeavor, and that meant tapping both friend and foe, because things were really complicated due to the high volume of double agents. When the war broke out, everyone had three choices: join the rebellion, join the Union, or become a spook, which meant pretending to join one side while actually joining the other. This was not rocket science and spooks were soon strategically placed throughout both power structures. Keep in mind, the Congress and Cabinet were pretty much equally divided, and people who’d worked together as friends for decades, were instantly transformed into mortal enemies.

Ability to break codes got one promoted faster than anything in spook world, and Secretary of War Edwin Stanton clearly had the best code-breakers on his side because they were constantly intercepting messages. On December 20, 1863, a ciphered telegraph message from the Confederate Secretary of Treasury to an engraver in New York City was cracked in a few hours and revealed the location of the printing press for Confederate paper money. Assistant Secretary of War Charles Dana supervised the confiscation and destruction of money and plates. The fact a New York engraver had been selected was just an indication New York was a hotbed for Democrats and Southern sympathizers, some of whom wanted to secede and join the rebellion. Cotton was North America’s biggest and most valuable export, and the price of cotton quickly rose from 10 cents a pound at the start of the war to a high of $1.89.

The South burned massive amounts of cotton in hopes of creating a cotton famine that would help force European countries into the conflict because their economies depended on cheap cotton. But Europe had been expecting supply issues, and had been stashing cotton, and would not require more cotton for years. A brisk smuggling trade developed between Nassau and Bermuda and the Confederate States. Ships arrived stuffed with cotton and departed stuffed with armaments. These voyages could reap a profit of 500 percent, so every $5 invested in raw cotton in Mississippi became $2,500 in British rifles in Virginia. There is simply no profit stream that can compete with war, which is why many on Wall Street remained so friendly with the South. War profiteering during the Civil War likely dwarfed anything made during Prohibition, which spawned a national crime organization, and although we have a decent scorecard on players in Prohibition, the Civil War profiteers remain largely uncelebrated.

Great Britain made a fortune selling armaments to the Confederates, and their rifles were vastly superior, nothing like the junk J.P. Morgan was selling the Union, although Morgan’s contracts were enforceable, his weapons were flawed and obsolete. By the end of the war Morgan and Jay Gould would rule Wall Street thanks to their successful profiteering. The difference was Morgan was an ally of the British bankers, while Gould yearned to be King Midas and tried to go up against them (and lost).

A ciphered message was discovered in a trunk in John Wilkes Booth’s hotel room after the assassination, and it matched the cipher being used by Jacob Thompson, head of Confederate Secret Service in Canada. But there were no messages from Thompson regarding any attempted assassination of Lincoln. Clearly, Booth was getting both money and assistance during the final weeks of his life, but it wasn’t coming from Richmond, where the kidnapping plot had been hatched. No, someone who knew about the kidnapping plot was suddenly putting up money for a hit, and this operation was manifesting at lightning speed.

The day after the assassination, Secretary of War Stanton sent a terse message to his former chief of detectives in New York City. Lafayette C. Baker had been in charge of Stanton’s Gestapo, the National Detective Police (NDP), but had recently been demoted and moved to New York after Stanton discovered him tapping the War Department telegraph line.  Baker arrived the following day and was given zero information, despite all the clues found in Booth’s hotel room and the abandoned room at the Kirkwood, not to mention the investigations of the Surratt boarding house. Somehow, Stanton had already concluded this house was a center of gravity regarding the assassination, and Mary Surratt was about to be turned into Stanton’s chief patsy. But he shared none of this information with his former chief of detectives, and only revealed the suspect was John Wilkes Booth, so go find him.

That meeting happening on Sunday. Two days later, a letter arrived at the War Department:
New York, April 14, 1865
Mr. Stanton
Dear Sir: If you want me you had better send for me.
J. Wilkes Booth
P.S. What do you say?

This was the first of several letters written in Booth’s hand that arrived at the War Department over the next week, each one postmarked further north, an obvious attempt to convince the NDP Booth had escaped into Canada. I suspect John Surratt’s mission in this plot was to seed these letters into Canada, because that’s where Surratt ended up, and the first one was undoubtedly posted the same day as the assassination, although the stamp is smudged beyond recognition.

But Baker must have suspected this letter was also Booth’s clue to a possible secret connection between himself and Stanton, and Baker would become suspicious of Stanton’s motivations and actions over the next few days. And knowing Stanton, I’m sure those feelings of distrust were shared equally, if not magnified, on his end against his employee. After the JFK assassination a similarly cryptic letter would be discovered addressed to a Mr. Hunt and written in the hand of Lee Harvey Oswald. For years, many assumed it was a reference to CIA officer E. Howard Hunt, although late suspicion fell more toward the benefactor of the John Birch Society, H.L. Hunt.