[1][2] He enrolled at Bowdoin College in Brunswick, Maine in 1949 with plans to join the ministry[3] and graduated cum laude in 1953 with high honors in history and is a member of Theta Delta Chi and Phi Beta Kappa.

[6] Pickering's four-decade-long career in Foreign Service included ambassadorships in Russia (1993–1996); India (1992–1993); to the United Nations (1989–1992); Israel (1985–1988); El Salvador (1983–1985); Nigeria (1981–1983); and Jordan (1974–1978).

[9] The same year, Republican senator Jesse Helms of North Carolina urged that Pickering be dismissed, arguing that he helped manipulate the country's elections.

[11] In both cases, President Ronald Reagan offered Pickering his full support and he secured him a job as United States Ambassador to Israel after his appointment in El Salvador.

[12] As ambassador to Israel, Pickering led the United States' criticism of an Israeli policy that expelled Palestinians accused of instilling uprising.

[13] Pickering stressed to Israeli prime minister Yitzhak Shamir that the United States considered the actions illegal and unhelpful for peace efforts.

[15] Pickering played a critical role as Ambassador during the First Gulf War, when he helped lead the United Nations Security Council's response to Iraq's invasion of Kuwait.

The New York Times declared that Pickering was "arguably the best-ever U.S. representative to that body" [17] and that the move was made simply because he overshadowed Secretary of State James A. Baker during the Persian Gulf Crisis.

"[23] Following the resignation of Secretary of State Warren Christopher in 1996, Pickering was reportedly a top contender for the post, but was ultimately passed over in favor of then-UN Ambassador Madeleine Albright.

[32] Pickering serves on the board of directors for CRDF Global and the American Iranian Council, an organization devoted to the normalization of relations between Iran and America.

[37] In 2012, along with former Chairman of the Joint Chiefs of Staff Admiral Michael Mullen, Pickering helped lead a State-Department-sponsored panel investigating the Attack on the U.S. diplomatic mission in Benghazi.

[38] In 2014, Pickering gave the keynote speech at the Student Conference on U.S. Affairs at West Point, New York, addressing the unique challenges that disaster preparedness poses to United States foreign policy planning.