Left to right, Eisenhower’s National Security Advisor Robert Cutler, Senator John F Kennedy, Dr. Harry A Wolfson, and Paul F. Clark, dinner chairman, stand together after Cutler, Kennedy and Wolfson were honored by the National Conference of Christians and Jews at the Hotel Statler in Boston, February 16, 1956 (Photo Credit: Boston Globe/Getty Images)

By David Kurlander

The legal saga of ex-National Security Advisor Michael Flynn is almost farcically polarized. Were Flynn’s alleged offenses treasonous, or extremely patriotic? Is the Justice Department’s decision to drop the charges against Flynn the end of a witch hunt, or the death of the rule of law? Was the Obama administration’s handling of the Flynn case a responsible response to misconduct, or the biggest scandal in presidential history? Given the dramatic nature of these queries, the telling origins of the National Security Advisor position have been oddly absent from the conversation. The tenure of the very first person to hold Flynn’s role, Boston kingmaker and Eisenhower appointee Bobby Cutler, was filled with political double-dealings and ethical conundrums that can perhaps give a modicum of clarity to the current ruckus.

Bobby Cutler’s credentials were impeccable. Like his remarkably high-achieving four older brothers, Cutler attended Harvard and gained entry into the powerful Porcellian Club. He graduated Phi Beta Kappa and as Class Poet in 1916, survived combat in France, and wrote two well-received, proto-Fitzgeraldian novels about upper-class love and loss—Louisburg Square and The Speckled Bird. He was first in his class at Harvard Law and became a powerful political attorney, orchestrating the 1930s campaigns of Boston New Deal democrats, like Mayor Maurice Tobin, and liberal-minded Republicans, like dynastic Senator Henry Cabot Lodge Jr.

Given his reputation as a bipartisan compromiser, Cutler got the tricky job during World War II of orchestrating the soldier vote for the 1944 presidential election, FDR’s unprecedented fourth run. Cutler managed a Congressional compromise between recalcitrant Southern Democrats—who feared that allowing soldiers to vote absentee would collapse draconian restrictions against African Americans—and Rooseveltian forces, who knew that the soldiers would lean FDR. After the War, Cutler returned home and became President of Old Colony Trust Company, a 200-year-old, Boston Brahmin-backed bank that was intimately tied up in governmental machinations concerning the United Fruit Company. That work, and his continued friendship with Eisenhower campaign manager Cabot Lodge Jr., ultimately swept him back into the White House, where he brought his reforming expertise to the National Security Council.

Congress created the Council in 1947, as part of the same sweeping National Security Act that established the CIA and the modern Department of Defense. The Act called for the NSC to have a staff that met regularly with the President, VP, CIA director, and Secretaries of State and Defense. For the rest of the Truman administration, however, the NSC was mostly toothless and disorganized, with the exception of issuing the iconic NSC 68, a 1950 memo that recommended a massive nuclear arms race with the USSR. Cutler crafted a March 1953 reimagining of the NSC as a tiered organizational system later dubbed “policy hill,” with Cutler himself atop the heap and in charge of planning far more formal weekly Council meetings. Cutler had brought himself into the center of the defense establishment, right as the Cold War was heating up. 

Over the next five years, Cutler’s collaboration with Eisenhower was so intimate that the president—an accomplished painter—presented him with a landscape of a mill and a meadow. While Eisenhower had given portraits to Marshall Plan administrator Paul Hoffman and golfer Bobby Jones, Cutler was the first person ever to receive a full pastoral scene. Cutler guided Eisenhower through nuclear buildup, through the U.S.-backed Iranian and Guatemalan coups, through the Atoms for Peace initiative, and through the tense balancing act of restraining Senator Joseph McCarthy’s increasingly aggressive purges of “subversives” without alienating the right wing of the Republican Party.

In this last department, Cutler’s power has in recent years taken on a more tragic and paradoxical air. In 2018, Cutler’s great-nephew, Peter Shinkle, published a remarkable biography, Ike’s Mystery Man: The Secret Lives of Robert Cutler. Shinkle revealed—with the use of diaries, interviews, and re-examinations of ignored innuendos—that Cutler was a closeted gay man, and tragically juxtaposed these discoveries with Cutler’s role in accepting McCarthy’s push to expose gay government employees.

McCarthy, most infamous for his attacks on alleged Communists in government, also zeroed in on what he dubbed “sexual perverts,” who he argued were vulnerable to blackmail and thus could not be trusted with state secrets. During the Eisenhower transition, FBI Director J. Edgar Hoover, at this point under McCarthy’s sway, obliquely accused two high-profile Eisenhower appointees, Appointments Secretary Arthur H. Vandenberg and Ambassador to the Soviet Union Charles Bohlen, of being gay. Vandenberg folded before a public scandal, but Bohlen fought McCarthy successfully through his confirmation. 

Shaken by the accusations, Eisenhower, with Cutler’s seeming approval, signed Executive Order 10450, which mandated investigation of new employees for “sexual perversion” across the entire government. By October 1953, just four months after the Order and with Cutler intimately involved in its implementation, 843 government employees had been fired for allegedly being gay, while another 2,283 had resigned. The Order further emboldened McCarthy. After McCarthy secured intel that the son of one of his fiercest rivals, liberal Wyoming Senator Lester Hunt, had been arrested for soliciting an undercover officer, he blackmailed the elder Hunt into declining a second term. Heartbroken, Hunt shot himself with a rifle in his Senate office.

Cutler ultimately managed to evade the very systems he helped establish, despite his passionate, somewhat public, and ultimately unrequited love for Skip Koons, a young, prodigious, and also-closeted naval intelligence officer. Shinkle posited that many in Washington were aware of Cutler’s sexuality, but that—recognizing the precarity of his position—did nothing to expose him. Instead, the press covered him as a mysterious bachelor, who was, according to one particularly dramatic 1955 New York Times profile, “Untouchable, Unreachable, and Unquotable.”

Michael Flynn is not Bobby Cutler, nor is Trump anything like Eisenhower. But as we digest increasingly tangled arguments about the ongoing legal controversy, we may be able to find conceptual grounding in the very human emotions—paranoia, competition, and the desire for access to the president—that lay at the origins of the peculiar National Security Advisor post and that define so much of the present administration.

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