They were the last two high-profile holdouts.
The bloody U.S.-Dakota War had been over for three years. Thirty-eight Dakota men had been hanged in Mankato. But white military and political leaders weren't satisfied.
They felt they had to show, once and for all, that they'd handled the Indian problem and the frontier was back in business for immigrant settlers who could replenish the fledgling Minnesota economy.
So just after noon on Nov. 11, 1865, 425 soldiers marched in formation to surround a specially constructed double gallows at Fort Snelling.
More than 400 St. Paul citizens turned out 150 years ago to watch the hangings of two Dakota leaders: Medicine Bottle and Shakopee. They had eluded soldiers for years, escaping across the Canadian border to Manitoba with more than 500 Dakota refugees from the war.
Their flight ended in January 1864, when Shakopee and Medicine Bottle stopped by the home of a white friend near Winnipeg's Fort Garry. That Canadian trader, John McKenzie, was secretly in cahoots with a U.S. Army major across the border in what would become Pembina, N.D.
McKenzie plied both Indian leaders with alcohol laced with drugs. Shakopee, then in his 50s, was dosed with chloroform and rendered unconscious. Medicine Bottle, in his mid-30s, struggled longer but several men subdued him. Both Dakota men were tied to dog sleds and taken to Pembina, then Fort Abercrombie, en route to Fort Snelling.
The Minnesota Legislature forked out $1,000 — big money in the 1860s — to McKenzie as a bounty. Trials were held and both men were convicted despite sketchy evidence that they had committed atrocities during the war. They were blamed in the death of Philander Prescott, 60, who had lived among the Dakota for more than 40 years. He was beheaded on the first day of the war as he fled toward Fort Ridgely.