Presidential countdown

To the most popular president

6: Barack Obama

5. Theodore Roosevelt

Theodore Roosevelt was too popular for his own good. Or rather, too popular for his own time. Roosevelt entered politics in the 1880s, when party bosses and their machine-like organizations controlled nominations, elections and the disbursement of offices. They spoke the language of democracy, but democracy was the last thing on their minds. Politics was for acquiring power, and power was,  among other things, for acquiring wealth. Roosevelt joined the Republican party, largely because the Democrats were the party of secession and rebellion, and because in New York City, where he was born and raised, Democratic politics was dominated by William Marcy Tweed, the epitome of Gilded Age corruption. Yet the alternative was hardly better. New York Republicans had a machine of their own, and a boss, Thomas Platt, whose comparative circumspection allowed him to remain in power long after Tweed went to prison.

It was Platt who brought Roosevelt to the attention of New York voters as a candidate for governor, after Roosevelt made a name for himself fighting in the Spanish-American War. With Platt's endorsement and guidance, Roosevelt won the 1898 election and took office as New York's chief executive.

At which point it became unclear who had been using whom. Roosevelt displayed an independence of mind Platt found disturbing and then infuriating. He sought means to rid himself of this turbulent Rough Rider.

As it happened, William McKinley lacked a vice president, the incumbent having died in office during McKinley's first term. Platt engineered the nomination of Roosevelt for vice president in 1900. Mckinley's manager Mark Hanna grew apoplectic. “Don't any of you realize there's just one life between that madman and the White House?!” he expostulated.

Hanna’s fears came true when McKinley was assassinated in 1901. Roosevelt took office as America's youngest president before or since. 

And he soon showed himself as independent of Hanna and the national party bosses as he had been of Platt. Roosevelt caught the surging wave of progressive reform and took the ship of state on a wild ride. He brought antitrust lawsuits against J. P. Morgan and John D. Rockefeller. He regulated the rates and behavior of America's railroads. He sponsored legislation to safeguard America's food and drugs. He interposed himself between workers and management in strikes that threatened to cripple the economy, and he did so for the first time in presidential history on the side of labor.

Ordinary Americans loved the show and loved the showman. In the dawning age of celebrity, mediated by mass circulation newspapers, they applauded his outsized ego—his compulsion, as his daughter said, to be “the bride at every wedding and the corpse at every funeral." 

When Roosevelt ran for election in his own right, in 1904, voters gave him the largest popular majority in American history until then. On the night of the victory it seemed there was nothing he couldn't do, with the overwhelming support of the people. 

Except hold his tongue. Stung by claims that he had become consumed by his ego, he made a self-denying pledge. He said he would treat his first, inherited term as a full term under the de facto rule against third terms, and would not run for reelection in 1908.

His wife couldn't believe her ears. Edith Roosevelt was his firmest supporter and was dismayed that he would be depriving the country of his leadership. She was no less dismayed wondering what she would do with him after he put down the reins of power.

Roosevelt soon realized his faux pas. He later said he would give his right arm to be able to take back that rash election night pledge. But he kept it, for the time being. He arranged the nomination of William Howard Taft, who was duly elected. Roosevelt sailed off to Africa for a safari.

Killing wild beasts didn’t slake his ambition. He took offense at certain decisions by Taft and decided America needed him again. He challenged Taft for the Republican nomination in 1912.

That year was the first in which primary elections preceded the national nominating conventions. Roosevelt's popularity carried him to decisive victories in the primaries, including in Taft's home state, Ohio.

But the primary votes in those days were only advisory. The Republican convention stood by Taft. Roosevelt bolted the party to run at the head of the Progressive ticket. He lost to Woodrow Wilson in the general election, but finished ahead of Taft.

The Republicans blamed him for their defeat, as well they might have. The wounds took years to heal. But after Wilson got reelected in 1916, the Republicans were willing to look to TR again. He might well have received their next nomination, but he died suddenly in 1919.