Regarding that "Obnoxious Order," Bruce Catton in his book, "Grant Moves South" explains it thusly:
(Regarding Grant's father, Jesse) "....More recently Jesse had taken great pride in the new fame which his son had won, and had made so much noise about it that Grant felt called on to rebuke him, in a letter which, for Grant, was amazingly cold and sharp. Now, with the cotton problem lying heavily on his stooped shoulders, Grant was to find Jesse making book with the very traders who were Grant's worst trial -- coming in, sly and insinuating, to help the men whose patriotism, as Grant believed, was to be measured by dollars and cents.
The whole business is a little less than crystal clear, but what happened apparently went like this: Jesse Grant, in Cincinnati, formed some sort of partnership with three brothers, Henry, Harmon and Simon Mack, merchants who traded as Mack and Brothers. Under this deal, Jesse and the Macks would go South to buy cotton in the military department controlled by Jesse's son, the General; the Macks would furnish the capital, Jesse would furnish the son -- who was in a position to say whether any trader in West Tennessee or northern Mississippi could buy and ship cotton at all -- and the profits would be split. And so, early in December, while Grant was trying to get his army down to the Tallahatchie, and while Sherman was hurriedly getting his own expedition on transports at Memphis with Porter's gunboats puffing in the stream, Jesse and the Macks came down to northern Mississippi to see General Grant.
At first, Grant was cordial enough -- glad, as any son might be, to meet businessmen who were good friends of his father. Then the truth of the matter dawned on him. What Jesse and the Macks wanted was permits to buy and ship cotton, and Grant's own authority was being put up for sale. By the next train, under orders, the Cincinnati merchants went back North, lacking permits. The Chicago newspaperman, Sylvanus Cadwallader, wrote that Grant was bitter, indignant and mortified; and on December 17, at Holly Springs, Grant put his fury into an order which would leave a queer enduring stain on his own name. This order, published for the guidance of the whole department, read as follows:
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 within twenty-four hours from the receipt of this order.
Post commanders will see that all of this class of people be furnished passes and required to leave, and any one returning after such notification will be arrested and held in confinement until an opportunity occurs of sending them out as prisoners, unless furnished with permit from headquarters.
No passes will be given these people to visit headquarters for the purpose of making personal application for trade permits.
Concerning all of which there is much to be said.
The first thing to say is that the brothers Mack, unfortunately, were Jewish. The second is that the Army officers of that time and place, infuriated by the activities of the traders who were infesting western Tennessee and northern Mississippi, had long since concluded that most traders were Jews (which was not at all the case) and were using the word "Jew" much as superheated Southerners at the same time were using the word "Yankee" -- as a catch-all epithet which epitomized everything that was mean, grasping and without conscience. The third is that there did exist then, in the United States, latent for years, but now suddenly blooming under forced draft, a violent Ku Klux spirit, hang-over perhaps from the recent Know-Nothing era, a spirit which could rise to what now seem incredible heights of misunderstanding and hatred for all people who were not Northern Americans of English descent. All of these, taken together, were reflected in Grant's famous General Orders Number 11.
On November 9, Grant had told General Hurlbut, at Jackson, to let no civilians go south of Jackson, adding the injunction: "The Israelites especially should be kept out." The next day he told General Webster, in charge of his railroad supply line: "Give orders to all the conductors on the road that no Jews are to be permitted to travel on the railroad south from any point. They may go north and be encouraged in it; but they are such an intolerable nuisance that the department must be purged of them." And on the day he issued General Orders Number 11 he wrote to C.P. Woolcott, Assistant Secretary of War, a detailed explanation of his action:
I have long since believed that in spite of all the vigilance that can be infused into post commanders, the specie regulations of the Treasury Department have been violated, and that mostly by Jews and other unprincipled traders. So well satisfied have I been of this that I instructed the commanding officers at Columbus to refuse all permits to Jews to come south, and I have frequently had them expelled from the department, but they come in with their carpet-sacks in spite of all that can be done to prevent it. The Jews seem to be a privileged class that can travel anywhere. They will land at any wood-yard on the river and make their way through the country. If not permitted to buy cotton themselves they will act as agents for someone else, who will be at a military post with a Treasury agent to receive cotton and pay for it in Treasury notes which the Jew will buy up at an agreed rate, paying gold. There is but one way that I know of to reach this case; that is, for Government to buy all the cotton at a fixed rate and sent it to Cairo, St. Louis or some other point to be sold. Then all traders (they are a curse to the army) might be expelled.
Grant's emotions are clear enough, and his idea about the best way to handle the cotton traffic was excellent, but his language was confused. He wanted to get the traffic under decent control so that he could get on with the war, and like many other officers at that time and place he was using the words "Jews" and "cotton traders" interchangeably. In the same way, Dana had been warning Stanton about the get-rich-quick mania that had infected "a vast population of Jews and Yankees," and Brigadier General Alvin P. Hovey, complaining about the bargain-hunting that was going on, was denouncing unprincipled sharpers, Yankees, bloodhounds of commerce, and Jews all in one sentence, making all of the words mean the same thing. Grant himself, later on, seemed honestly puzzled by the furore his order had raised. Talking with a rabbi after the war, he tried to explain what he had done: "You know, during war times these nice distinctions were disregarded. We had no time to handle things with kid gloves. But it was no ill-feeling or a want of good-feeling towards the Jews. If such complaints" --that is, complaints about extortionate practices in the cotton trade -- "would have been lodged against a dozen men each of whom wore a write cravat, a black broadcloth suit, beaver, or gold spectacles, I should probably have issued a similar order against men so dressed."
There were some odd aspects to the whole business. A week before Grant issued his order, the Commanding Officer at Holly Springs, Colonel John V. Dubois, announced that "all cotton speculators, Jews and other vagrants having no honest means of support except trading on the miseries of their country" must leave town within twenty-four hours or be conscripted into the Army; Grant revoked this order and Dubois was transferred to other duty -- an unfortunate shift, perhaps, since he was replaced by the Colonel Murphy who would surrender so meekly when Van Dorn demanded it. There was also persistent gossip to the effect that Grant himself did not devise General Orders Number 11. Old Jesse told Congressman Washburne that the order was issued on instructions from Washington; several newspaper stories said the same thing; and one witness asserted that one of Grant's subordinates prepared and issued the order without Grant's knowledge. But however all of this may have been, the order did come out -- to stand as a melancholy example of the kind of prejudice which was taken for granted in the 1860's."
Catton's sources and notes:
1. "The deal between Jesse Grant and the Mack brothers is set forth in detail in a lawsuit which Jesse filed against the brothers in Cincinnati courts early in 1863 -- a bit of litigation which the judge non-suited, and which is described in the New York Tribune, September 19, 1872. See also Nelson Cross, The Modern Ulysses, LL.D.: His Political Record, p. 76; and William B. Hesseltine, Ulysses S. Grant, Politician, pp. 30-31. There is an extensive discussion of the rather singular relationship between Grant and his father in Captain Sam Grant."
2. Grant's General Orders No. 11, dated December 17, 1862, in O.R., Vol. XVII, Part Two, pp. 330, 337, 421-422.
3. Dana, Recollections, p. 18; Hovey to Brig. Gen. Fred F. Steele, December 5, 1862, in O.R., Vol. XVII, Part One, p. 532. Sherman's correspondence, and that of other Army officers for this period, bristles with references to the activities of "Jewish traders."
4. Chicago Tribune for April 9, 1885, an interview with Rabbi Browne, who quoted his own diary entry for an interview with Grant on Aug. 27, 1875.
5. The details as to Colonel Dubois are in the Chicago Tribune for December 18, 1862, in a dispatch from Oxford, Mississippi. See also J.R. Grant's letter to Washburne dated Jan. 20, 1863, in the Washburne Papers; undated clipping from the Cincinnati Commercial, apparently for early January, 1863, in the Lloyd Lewis Papers; New York World, August 18, 1863; Otto Eisenschiml, "Anti-Semitism in Lincoln's Times," in the Chicago Forum, Vol. I, No I, p. 11.