free his slaves. However, Coles developed a good relationship with Madison, with whom he would often speak with "perfect candor", and formed a lasting admiration for the president. While Madison's secretary, Coles initiated private correspondence with Thomas Jefferson over the issue of slavery, as discussed below. Coles gained political experience as Madison's assistant, served as his primary emissary to Congress, and managed much of the patronage flowing from the 162-employee executive branch. Among other duties, Coles hand-copied the president's official correspondence for the national archives. Coles met John Adams during a tour of north-eastern states in 1811. Along with Benjamin Rush, Coles worked to diminish tensions and rewarm relations between Adams and Thomas Jefferson. Coles also spent considerable time in Philadelphia receiving medical treatment from Dr. Physick, among others, as well as began a long friendship with Nicholas Biddle, who became controversial as a banker and anti-slavery advocate. As the War of 1812 ended, Coles resigned due to continued ill health in February, 1815. Upon recovering in June, Coles and his 40-year-old mulatto slave and coachman, Ralph Crawford, toured the Northwest Territory in search of land Coles could purchase and develop as a home for himself and a place for the slaves he still proposed to free. Coles wrote letters to President Madison and to relatives expressing dissatisfaction with the high land prices in Ohio, then with squatters, real estate speculators and fraudulent businessmen as he travelled further west into the Indiana (and what became the Illinois) Territory. In the Missouri Territory Coles bought some land for investment, before finally embarking in St. Louis on a keel boat for his trip down the Mississippi River to New Orleans, from where Coles ultimately sailed home to Virginia. Coles was delayed again in fulfilling his covenant with freedom by a diplomatic trip to Russia (1816–1817) at President Madison's request, to resolve a diplomatic incident concerning the Russian consul's arrest in Philadelphia for raping a maid. After successfully completing his mission in St. Petersburg, Coles toured Brussels, Paris and England. While in England, Coles met ambassador John Quincy Adams and social reformer Morris Birkbeck. Coles extolled such enthusiasm about Illinois that Birkbeck bought land, moved and established a settlement. Upon his return, Coles wrote a paper comparing slavery and Russian serfdom, so if an ulterior motive for the diplomatic assignment was dissuading Coles from his manumission plan, it failed. Moreover, Coles wrote about