And now… something to infuriate both conservative and liberal myth-makers: The president conservative icon Ronald Reagan most resembled is that great faux liberal John Fitzgerald Kennedy. The resemblances last even unto the grave. JFK was, of course, the martyred hero because of his assassination on November 22, 1963. Reagan survived an assassination attempt on March 30, 1981, but his death from Alzheimer's disease in 2004 is often viewed in comparable tragic light.
How they are similar:
It begins with the fact that each was so charismatic that they were style setters: JFK (and his wife Jackie) was the poster child for the 1960s emphasis on youth; Reagan raised the bar on avuncular charm. Both were viewed as emblems of a new era: JFK as an end to the paranoia and witch hunts of the dour 1950s; Reagan as the end of the Sixties and as a symbol of free enterprise unleashed. In each case, their reputations exceeded their actual accomplishments. Both became legends, but I remind you that, in scholarly terms, legend occupies the middle position between factual history on one end and faith-based myth on the other.
Kennedy's numerous affairs became public knowledge only in death, but they were many and varied. Reagan is the only divorced president in U.S. history. (A Trump presidency would raise the number to three.) He cheated on his first wife and was an infamous Hollywood horn-dog before marrying Nancy in 1952. There is a lingering allegation that Reagan raped actress Selene Walters. Nancy is said to have carried on a long-term affair with Frank Sinatra.
JFK isn't known as a tax cutter, but he was; he reduced the graduated income tax rate from 20-90% to 14-65%, thereby handing the 1% a sizable handout. Reagan, of course, put into effect one of the biggest tax cuts in U.S. history. As a result, both presidents ran deficits: JFK the first since the end of World War Two (though he retired it) and Reagan the largest peacetime deficit (in real dollars) the nation had seen. (It has since been surpassed.)
Both presidents enjoyed low inflation. Neither was a particularly stalwart steward of the economy, reputations to the contrary notwithstanding. Kennedy enjoyed the postwar economic boom, but played a minimal role in advancing it. Reagan gets credit for ending stagflation and that is imaginative mythmaking. Supply side economics had very little to do economic recovery and those who benefitted from Reagan tax cuts mostly pocketed their saving rather than reinvesting in the economy. The Reagan years look good only in comparison to the 1970s; economic growth and the overall economy were far more robust in the 1960s. Moreover, job and family income growth in the 1980s was due almost entirely to three sources: the expansion of the low-wage service sectors, the record entry of women into the workplace, and the early wave of the new and unforeseen technology industry.
Neither man was strong on civil rights, though JFK gets more credit than he deserves. JFK did eventually send troops to quell violence associated with the Freedom Rides, marches and the attempt of James Meredith to enter the University of Mississippi, but he did so only under duress. JFK feared losing Southern votes at a time in which the region was a Democratic stronghold, and acted only in the face of outrageous Southern intransigence. He also authorized limited wiretaps on the Rev. Martin Luther King, Jr. Reagan saw civil rights as a violation of states' rights and was probably a closet racist. He wanted to allow the Voting Rights Act to expire in 1981, but intense pressure forced him to extend it for ten years. Congress overrode his veto of the Civil Rights Restoration Act of 1988.
Kennedy was stronger on support for labor unions than Reagan, though his administration rode both unions and U.S. Steel hard in 1962. Kennedy famously called parts of the business community "sons of bitches," but he imposed his will on both sides and cracked down on perceived union corruption. Reagan infamously broke the air traffic controllers' union and unleashed an assault on unions that left them reeling to the present day.
Both presidents delivered bold but hollow promises. JFK's domestic achievements were actually rather thin, once one gets past the Peace Corps. His rhetorical support for civil rights was strong; his delivery very weak. Reagan pleased cultural conservatives with his rhetoric, but did almost nothing to deliver on cherished agendas such as bringing back school prayer, overturning Roe v. Wade, or banning flag burning. His most notable attempt at stemming drug abuse—which reached record highs in the 1980s—was the much ridiculed and wholly ineffective "Just Say No" campaign. Historians now speculate that Reagan had very little genuine interest in these issues; despite his courting of evangelical support, Reagan was among the least religious presidents in American history.
Like Reagan, JFK was a strong law and order advocate. JFK allowed the last federal execution to take place and rather famously allowed his brother, Attorney General Robert Kennedy, to go after organized crime, especially within the Teamsters union.
Now for the biggies: Both men were Cold War presidents par excellence. JFK's résumé includes: green-lighting Eisenhower's foolish Bay of Pigs invasion, witnessing the building of the Berlin Wall, the Cuban Missile crisis, considering the assassination of Rafael Trujillo in the Dominican Republic, increasing the number of U.S. military advisors to Vietnam, unleashing the CIA across globe (including its possible role in assassinating Diem in Vietnam), setting up the Alliance of Progress in Latin America to counter perceived communist advances in the region, and (ahem!) involving the U.S. in a border dispute—rooted in oil politics–between Iraq and Kuwait. Kennedy increased the defense budget to counter a perceived "missile gap" vis-à-vis the Soviet Union. On the plus side, he did approve a Partial Test Ban Treaty with the USSR and outlined plans to reduce nuclear weapons. But of all the myths surrounding Kennedy, few are bigger than the idea he planned to pull out of Vietnam. That's doubtful: his team was the very architect of US military intervention in Southeast Asia.
Reagan was the last Cold War president, but not a very thoughtful one until very late in his second term. Reagan raised tensions by calling the USSR an "Evil Empire," and proceeded to raise defense spending to levels that created massive deficits. Lots was squandered on things that didn't work, including the Strategic Defense Initiative, the neutron bomb, tanks that broke down, and fighter planes with flawed designs. He armed Taiwan, which angered China, and his Reagan Doctrine supported authoritarian regimes across the world if those governments were anti-communist. This was especially the case in Latin America, where the US supported brutal regimes in Guatemala, El Salvador, Honduras, Peru, and Chile. Reagan was obsessed by the Sandinista government of Nicaragua and got embroiled in his own Bay of Pigs scenario: the Contra scandal (linked with Iran) that could have (perhaps should have) led to his impeachment. In another reckless maneuver, the Reagan team armed the Mujahedeen in Afghanistan, including aid to Osama bin Laden. It wasn't until 1988 that Reagan realized the Cold War was ending and signed the INF Treaty with the USSR, but the claim that he "won" the Cold War is a myth on par with JFK's post-1964 plan for Vietnam.
The idea that Reagan was a "strong" leader also fails to pass historical muster. His foreign policy was bungling and often foolish. Like Jimmy Carter, Reagan saw several hostage crises during his presidency; unlike under Carter, not all hostages came home alive. Reagan's attempts to negotiate with Iran for hostage release—while publicly belittling Iran–yielded little except increased contempt on the part of Iranian leaders. Numerous Reagan initiatives were filled with strong talk and weak action, including the ill-defined peace mission to Lebanon that led to the death of over 300 US troops. His one "victory," was the invasion of the tiny Caribbean island of Grenada. Its invasion—just two days after 241 Americans died in a suicide bombing in Beirut–invites cynicism.
How they are different:
They differed in ideology: Kennedy was a Cold War liberal and Reagan a Cold War conservative. In addition, Kennedy was nominally a Keynesian economically, and Reagan a supply side advocate. As I have argued, this probably mattered more on paper than in reality, but Kennedy–had he lived–would have been far more likely to institute social and economic reforms. Kennedy was an advocate of positive government and Reagan of negative government, meaning that JFK was more willing to see government as the engine of social change, whereas Reagan advocated limited government power.
JFK's intellect far surpassed that of Reagan, who was never known as a deep thinker. Kennedy did not share Reagan's belief in deregulation; he was also more likely to support protectionist policies if he felt US industry was threatened.
Reagan's administration was the most indicted in US history, whereas JFK's was relatively scandal-free. This had something to do with changing times, but it also had much to do with the contempt with which Reagan officials felt for Congress and (by extension) U.S. law.
Conservatives want to put Reagan on Mt. Rushmore. It won't happen, nor should it. JFK currently ranks 11th (of 42) and Reagan 15th. Neither of these ratings will stand. In each case, style currently reigns over substance. Look for each to move down, once the romance associated with each figure fades.