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While Jessup was capturing Seminoles under flags of truce, Cherokee leader John Ross attempted to bring about a peaceable settlement. The politically savvy Ross hoped that by playing the role of negotiator he could possibly stall or stop the removal of the Seminoles, which could help the prospects of the Cherokees. <ref> Moulton, p. 296</ref> Ross and a contingent of Cherokee leaders traveled to Florida in late 1837 to meet with representatives of the Seminoles and the American government and asked for the release of Seminole prisoners as a sign of good faith. The peace talks ended with no agreement and no prisoners were released – Osceola died on January 30, 1838 after languishing for three months in prison. <ref> Moulton, p. 304</ref>
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===Zachary Taylor Comes to Florida===
[[File: Zachary_Taylor_by_Joseph_Henry_Bush.jpg|300px|thumbnail|left|Zachary Taylor (1784-1850) (President of the United States March 9, 1849 – July 9, 1850) ]]
Fresh off his campaign in the Black Hawk War, Zachary Taylor was promoted to Brigadier General and given command of Florida. Taylor immediately set to work rectifying what he believed were mistakes made by Jessup by dividing the territory north of the Withlacoochee River in northwestern Florida into twenty miles square sectors and placed twenty men garrisons in each. He also organized incursions deeper into the Everglades using bloodhounds to track Seminole warriors. <ref> Adams, p. 370</ref> The results of Taylor’s tactics were negligible at best and even he began to see that leaving the Seminoles in the swampy Everglades was probably the best course of action.
Removal was postponed in March 1839 and a <i>de facto</i> cease fire followed with peace negotiations at Fort King on May 18, 1839. The talks involved Taylor, General Alexander Macomb, and Colonel Harney for the army, while chiefs Chitto Tustenuggee and Halleck Tustenuggee represented the Seminoles. The Americans agreed to quit pursuing the Seminoles if they stayed south of the Pease Creek, which is located just south of the modern Tampa Bay metropolitan area. It looked like peace would return to Florida, but just as with the early treaties, four of the major bands did not participate. <ref> Adams, p. 372</ref>