As he gains strength as a candidate for the 2020 Democratic presidential nomination, Michael Bloomberg is trying to buck the venerable tradition of New York mayors (and former mayors) running unsuccessfully — and sometimes incompetently — to become chief executive.
The first to do so may have actually had the best chance to win: DeWitt Clinton, who was serving his tenth year as mayor when he challenged James Madison’s reelection in 1812 with the backing of Federalists and fellow antiwar (the War of 1812 had just begun) Democratic-Republicans. He won seven states — including New York — but Madison won the Electoral College by a 128-89 margin.
Subsequently four governors of New York (Martin Van Buren, Grover Cleveland, Theodore Roosevelt, and Franklin Roosevelt) became president, and many others ran for the presidency (the most recent major-party nominee in that group was Thomas Dewey in 1944 and in 1948). Though New York mayors were often national figures of note, and occasionally the object of presidential rumors, none actually ran until John V. Lindsay in 1972. Lindsay anticipated Bloomberg in some respects: He was originally elected as a Republican, but after losing the GOP primary in 1969, he won reelection on the Liberal line and then formally became a Democrat before launching his presidential bid. Despite some high expectations, the famously telegenic Lindsay bombed in Florida and Wisconsin and dropped out of the race early on.
There was a small effort to draft Ed Koch into the 1984 Democratic race, but he wisely declined, though it would have been fun to see him in Iowa trying to defend sardonic comments on the idiocy of rural life. The next mayor of New York to run for president was a figure who is still all up in our grill: Rudy Giuliani.
An early polling leader for the GOP nomination in 2008, despite his occasionally heterodox views on cultural issues, Giuliani chose to ignore the “book” and skipped Iowa and (initially) New Hampshire, staking everything on a late-January primary in Florida. He finished third in the Sunshine State, and dropped out of the race the next day, becoming a cautionary tale about the value of early polls and the wisdom of defying the Great Corn Idol of Iowa.
Compared to the next New York mayoral bid for the White House, however, Rudy’s was a model of strategic brilliance and efficiency. Current mayor Bill de Blasio, despite near-universal discouragement from everyone with his ear, decided to run for the 2020 Democratic nomination. His campaign became an ongoing bloopers show. At one point in Iowa, he chose to ignore warnings of an approaching blizzard, and got stranded in a small-town Super 8 motel, where (according to the New York Post, whose reporters followed his meanderings closely with malicious glee), he dined on a microwaved gas-station burrito. After never showing any signs of popular support anywhere, de Blasio finally quit the race in September of 2019.
So that brings us to 2020 and Bloomberg. Interestingly enough, he’s emulating Giuliani’s skip-the-early-states strategy, but he’s putting his vast wealth into ensuring that when the calendar does turn to Super Tuesday in March he will be extremely well-known and have a solid campaign in those states. And it’s looking like he is lucking into a landscape in which all of his surviving rivals will have weaknesses he can exploit. Whether it’s a one-on-one cage match with current front-runner Bernie Sanders, or a large field of wounded and underfunded candidates struggling from state to state, Bloomberg is positioned to do a lot better than Rudy did and perhaps as well as or even better than DeWitt Clinton. If he blows this opportunity, it could be a long time before another New York mayor ventures onto the presidential campaign trail.