Image from library.yale.edu
The American Civil War is steeped in enough myth and legend and accounts differing across the Mason-Dixon line that the truth might be difficult to track down. Judah Philip Benjamin didn't help historians much by staying quiet about his role in the Confederate government, despite allegations against him so damning that they forced his flight from the country.
Born in 1811 on the island of St. Croix in what are now the Virgin Islands, Benjamin later moved with his family to South Carolina. He attended Yale when he was only 14 years old, though he evidently left before graduation under mysterious circumstances. Moving to New Orleans, Benjamin entered the business of law but also dabbled in railroad development and sugar planting. He owned some 140 slaves until he sold his plantation in 1850.
In 1842, Benjamin was elected as a Whig to the Louisiana state legislature and subsequently became the second Jew to be elected to the U.S. Senate in 1852. When the Whig Party dissolved under the mounting pressures leading to the Civil War, Benjamin became a Democrat. After Louisiana seceded to join the group of states forming the Confederacy in 1861, Benjamin left the Senate and was appointed Attorney General of the Confederate government by president Jefferson Davis.
Though widely regarded as a capable official, Benjamin was not the most popular member of the cabinet, with some scholars attributing this to anti-Semitism. In September 1861, he was appointed the Confederacy's second Secretary of War. Clashing with military leaders, Benjamin was held accountable for the loss of Roanoke Island to Union forces as well as other losses in the western theater. Henry Foote, the Tennessee representative in the Confederate Congress, introduced a bill of no confidence against Benjamin in 1862.
Davis, not wanting to lose Benjamin's expertise, encouraged him to resign and appointed him as the Confederacy's third Secretary of State. Benjamin focused his efforts on cultivating diplomatic relations with England and France, including securing the Erlanger Loan, in which a French banking house agreed to market $15 million in Confederate cotton bonds to inject much-needed capital into the Confederacy's economy. Benjamin was still dogged by political enemies, however, who accused him of smuggling and transferring money to personal bank accounts in Europe. The rumors tended to focus on similar misconduct, with accusations that Benjamin had left Yale for thievery and stole money from the treasury when the cabinet had to vacate Richmond (the cabinet did pack up the treasury upon departure, however, and people are still trying to track down that gold).
Though it was advocated by other government and military officials as well, Benjamin came under fire for suggesting that slaves be allowed to fight for the Confederacy in exchange for emancipation. A subsequent vote in the Confederate Congress to find him "not a wise and prudent Secretary of State" failed in a tie. Despite being a controversial figure, Benjamin's likeness was printed on the Confederate two-dollar bill.
Benjamin's move through cabinet positions was more a result of the instability of the Confederacy than any proven scandal. It was a series of events toward the end of the war that made reconciliation with the United States an impossibility for him. By that time, he had become involved in covert activities against the United States, including encouraging dissent and funding spy rings operating out of Canada. This would not bode well for him when the cabinet fled the capital before its fall to Union forces. In April of 1865, John Wilkes Booth assassinated U.S. President Abraham Lincoln. In the aftermath of the shooting, Benjamin didn't come off in the best light. He'd burned documents before leaving Richmond and had financed an operation that aimed to kidnap Lincoln. How closely the Confederate spy operations were tied to the conspirators is unclear, but prior to the assassination Booth opened an account in the same bank that was a drop point for Confederate cash, and John Surratt (son of Mary Surratt, an assassination conspirator who was later convicted and hanged) ferried money to Confederate agents in Canada. William Seward, the United States Secretary of State, had been wounded in an assassination attempt connected to that on Lincoln and said he thought Benjamin had been the sole Confederate cabinet member in on the plot.
Benjamin was not the only one implicated in the assassination; Davis's name showed up frequently as well. Historians seem to agree that Benjamin had no part in the plot, saying the accusations arose out of a mixture of anti-Semitism and people offering testimony against the Confederate government officials in hopes of collecting a reward. However, fearing that he would not receive a fair trial in such an atmosphere, Benjamin fled in disguise. After a four-month journey, he departed the country by boat from Florida, escaping to the Caribbean before crossing the Atlantic to England. Davis was captured and indicted for treason, but the charges were later dropped; the story of the former Congressman, Senator, and Secretary of War from Mississippi is surely enough for a future entry.
Benjamin made his way to England, where he quickly settled into a career as a successful barrister. In 1872, he was elected to the Queen's Counsel. He died in 1884 on a visit to France, having never publicly spoken or written about his time in the Confederate government.
Sources: Biographical Directory of the United States Congress, Leaders of the American Civil War: A Biographical and Historiographical Dictionary edited by Charles F. Ritter and Jon L. Wakelyn, Encyclopedia Britannica, "Judah Benjamin, The Jewish Confederate" by the American Jewish Historical Society, The Jewish Confederates by Robert N. Rosen, Blood on the Moon: The Assassination of Abraham Lincoln by Edward Steers Jr., The Rebel and the Rose: James A. Semple, Julia Gardner Tyler, and the Lost Confederate Gold by Wesley Millett and Gerald White