Judah Philip Benjamin was born on August 6, 1811, in St. Croix of the Danish West Indies (today the United States Virgin Islands), a colony that was under British occupation during the Napoleonic Wars.

According to Rabbi Bertram W. Korn's volume on that city's Jews, he "arrived in New Orleans in 1828, with no visible assets other than the wit, charm, omnivorous mind and boundless energy with which he would find his place in the sun".

Daniel Brook, in a 2012 article about Benjamin, suggests that early biographies read as though "historians are presenting him as an almost farcically stereotypical gay man and yet wear such impervious heteronormative blinders that they themselves know not what they write".

Considering the character of the slave, and the peculiar passions which, generated by nature, are strengthened and stimulated by his condition, he is prone to revolt in the near future of things, and ever ready to conquer [i.e. obtain] his liberty where a probable chance presents itself.

But the high incidence of Jewish assimilation, the availability of the black as a scapegoat for social ills, and the relative absence of crises—economic and otherwise—were factors which repressed, at least temporarily, the latent anti-Jewish feeling in the South.

[23] This purchase, and the subsequent construction of a grand house there, advanced Benjamin's ambitions; the planter class controlled Louisiana politics and would trust only a man who also owned substantial land and slaves.

[29] The following year, Benjamin assisted the United States Attorney in New Orleans in prosecuting American adventurers who had tried to spark a rebellion against Spanish rule in Cuba, but two trials both ended in hung juries.

[27] Benjamin became interested in strengthening trade connections between New Orleans and California, and promoted an infrastructure project to build a railroad across the Mexican isthmus near Oaxaca; this would speed passenger traffic and cargo shipments.

[50] In 1859, Benjamin was elected to a second term, but allegations of involvement in land scandals and the fact that upstate legislators objected to both of Louisiana's senators being from New Orleans stretched the contest to 42 ballots before he prevailed.

Castillero had leased part of his land to British mining companies, and when American authorities ruled the grant invalid, they hired Benjamin; he spent four months in San Francisco working on the case.

The local correspondent for The New York Times wrote that Benjamin, "a distinguished stranger", drew the largest crowds to the courtroom and "the Senator is making this terribly tedious case interesting".

[60] With Southern opinion turning in favor of secession, Benjamin made a farewell speech in the Senate on December 31, 1860, to a packed gallery, desirous of hearing one of the South's most eloquent voices.

[79] Judah P. Benjamin, the dapper Jew, Seal-sleek, black-eyed, lawyer and epicure, Able, well-hated, face alive with life, Looked round the council-chamber with the slight Perpetual smile he held before himself Continually like a silk-ribbed fan.

Once it was put down, Benjamin and Davis were in a quandary about what to do about its leader, William "Parson" Brownlow, who had been captured, and eventually allowed him to cross to Union-controlled territory in the hope that it would cause Lincoln to release Confederate prisoners.

Distant from Jackson's other forces and ill-supplied, Loring and other officers petitioned the War Department to be recalled, and Benjamin, after consulting Davis, so ordered after he used the pretext of rumored Union troop movements in the area.

Benjamin and Davis hoped that the island's defenses could hold off the Union forces, but an overwhelming number of troops were landed in February 1862 at an undefended point, and the Confederates were quickly defeated.

Varina Davis noted that some in Congress had sought Benjamin's ouster "because of reverses which no one could have averted, [so] the President promoted him to the State Department with a personal and aggrieved sense of injustice done to the man who had now become his friend and right hand.

Much of this was due to hatred of slavery, though part of it stemmed from a desire to remain on good terms with the U.S. government—due to a drought in 1862, Britain was forced to import large quantities of wheat and flour from the United States.

[110] The bloody standoff at Antietam in September 1862 that ended Lee's first major incursion into the North gave Lincoln the confidence in Union arms he needed to announce the Emancipation Proclamation.

[113] In October, the British Chancellor of the Exchequer, William Gladstone, expressed confidence in Confederate victory, stating in Newcastle, "There is no doubt that Jefferson Davis and other leaders of the South have made an army.

[116] Although proponents of intervention were prepared to await another opportunity, growing realization among the British public that the Emancipation Proclamation meant that Union victory would be slavery's end made succoring the South politically infeasible.

[120] Baron Frederic Emile d'Erlanger, head of the firm, journeyed to Richmond in early 1863, and negotiated with Benjamin, although the transaction properly fell within the jurisdiction of Treasury Secretary Memminger.

Although efforts were made to boost Peace Democrats, the most prominent actions proved to be the St. Albans Raid (an attack on a Vermont town from Canada) and an unsuccessful attempt to burn New York City.

"[132] The year 1864 was a disastrous one for the Confederacy, with Lee forced within siege lines at Petersburg and Union General William T. Sherman sacking Atlanta and devastating Georgia on his march to the sea.

Nevertheless, Benjamin retained his usual good humor; on the evening of April 1, with evacuation likely, he was at the State Department offices, singing a silly ballad of his own composition, "The Exit from Shocko Hill", a graveyard district located in Richmond.

Navy Secretary Stephen R. Mallory recorded that Benjamin's "hope and good humor [was] inexhaustible ... with a 'never-give-up-the-ship' sort of air, referred to other great national causes which had been redeemed from far gloomier reverses than ours".

With no army to shield the Confederate government, it would be captured by Union forces within days, so Davis and his Cabinet, including Benjamin, fled south to Greensboro, North Carolina.

His escape from Florida to England was not without hardship: at one point he pretended to be a Jewish cook on Tresca's vessel, to deceive American soldiers who inspected it—one of whom stated it was the first time he had seen a Jew do menial labor.

[173][172] Edgar M. Kahn, in his journal article on the 1860 California sojourn, wrote, "Benjamin's life is an example of a man's determination to overcome almost insurmountable barriers by industry, perseverance, and intelligent use of a remarkable brain.

[125] Reform Rabbi Daniel Polish noted in 1988 that Benjamin "represent[ed] a significant dilemma [in] my years growing up as a Jew both proud of his people and with an intense commitment to the ideals of liberalism and human solidarity that I found embodied in the civil rights movement.