An 1864 photo of General Ulysses S. Grant Public domain via Wikimedia CommonsAs Union General Ulysses S. Grant pushed southward from Tennessee into Oxford, Mississippi, in December 1862, he felt the pressure of the Southern cotton economy closing around him.Smuggling and corruption were rampant in his new military district, which stretched from Mississippi to Kentucky.So the general made a rash choice in his attempt to crack down on an underground cotton trade by ordering the expulsion of all Jews from his district.The move not only played into antisemitic tropes but also affected his reputationand his future political career.Grants order responded to an unsettling economic reality: Despite the war raging around them, Southern planters still wanted to sell their cotton, and Northern mills still wanted raw material to make into textiles and garments.Grant had to deal with swarms of Northern traders who maneuvered to cash in on the North's consuming need for this major export, Ron Chernow wrote in his biography Grant. The black market for cotton infuriated the general, not least because the illicit trade of goods might also run parallel to the spread of crucial military information. An 1863 photograph of Grant Public domain via Wikimedia CommonsGrant was particularly upset after his father, Jesse Grant, visited Oxford with Harmen, Henry and Simon Mack, three brothers from a family of prominent Jewish clothiers in Cincinnati. The Macks hoped to secure a cotton purchasing permit from the general, promising his father 25 percent of the profits. Grant did not take this proposed bargain well and sent the Macks packing.On December 17, Grant announced a bold order designed to stop the griftone that historians like Chernow have called the most egregious decision of his career.Instead of targeting unscrupulous merchants specifically, he ordered the expulsion of all Jews from his district, echoing a longstanding antisemitic stereotype of Jews as amoral and untrustworthy traders and moneylenders.Issued from his headquarters in Oxford, Grants General Orders No. 11 read that the Jews, as a class, violating every regulation of trade established by the Treasury Department, and also department orders, are hereby expelled from the department.The measure afforded Jews 24 hours to leave the military district. It stated, Anyone returning after such notification will be arrested and held in confinement until an opportunity occurs of sending them out as prisoners.In a letter sent back to the Department of War on the same day, Grant elaborated that Jews and other unprincipled traders come in with their carpet sacks in spite of all that can be done to prevent it. Beyond expulsion, he suggested that the government itself should purchase cotton at a fixed rate to prevent speculation and price gouging.As the order began to go into effect, the Daily Missouri Republican reported a general stampede and great consternation among Hebrew merchants.Cesar Kaskel, a Jewish immigrant from Prussia who had settled in Paducah, Kentucky, received the news of his expulsion on December 28, according to historian Jonathan D. Sarnas When General Grant Expelled the Jews.Incensed that his loyalty to the Union, despite living in a Confederate state, counted for nothing, Kaskel tried to fight the expulsion order. He wrote to the press, arguing that he was a peaceable, law-abiding citizen, pursuing my legitimate business who was nevertheless expelled because I was born of Jewish parents. An 1882 cartoon depicting Grant crying "crocodile tears" over the persecution of Jews in Russia Public domain via Wikimedia CommonsNext, Kaskel dispatched a telegram to the White House, asking Abraham Lincoln for his effectual and immediate interposition. When that didnt work, he set off for Washington on a Paul Revere-like ride, as Sarna put it, spreading news of Grants controversial order along the way.Kaskel eventually gained access to Lincoln, who learned of Grants order for the first time. On January 4, 1863, Lincoln ordered Grant to repeal the expulsion, but even in the aftermath, the order continued to hound him.During Grants 1868 campaign for the presidency, Americansparticularly American Jewswrangled with the issue. The American Israelite, a Jewish newspaper, spent a whole broadsheet page struggling with the matter of voting for Grant without coming to a meaningful conclusion. Others condemned Grants cool, deliberate malice and worried what he would do once in power.After he was elected, however, Grant tried to make amends. He appointed a record number of Jewish Americans to the government, attended the dedication of a synagogue in Washington in 1876 and condemned Jewish persecution in other countries.In a letter to Isaac N. Morris, a Jewish congressman, Grant apologized and said he sent the order without any reflection, and without thinking of the Jews as a sect or race to themselves.I have no prejudice against sect or race but want each individual to be judged by his own merit, Grant wrote. Order No. 11 does not sustain this statement, I admit, but then I do not sustain that order.Get the latest stories in your inbox every weekday.