It was a perfect storm with two potential directions: the Presidency or anonymity. Senator Thomas C. Platt, the “easy boss” of the Republican machinery, had more than enough of Governor Roosevelt’s inability to follow his lead. The 1900 Presidential election was around the corner; William McKinley was seeking reelection. McKinley’s Vice President Garrett Hobart had died the year before. It was just the opportunity Platt wanted to “kick Roosevelt upstairs.”

Of course, there was also the slight wrinkle that TR did not want to be Vice President.

His interest was in staying in the Governor’s Mansion.

McKinley was also an incredibly popular President; two terms of a well-liked Republican President would be a great lead-in to a Roosevelt bid for the Presidency in 1904. The fly in that ointment would be that if TR was reelected as New York’s Governor, he would be out of office by 1902, and quite possibly forgotten by ’04.

But becoming Vice President was not the way of the day to the Presidency.  After Martin Van Buren until that moment, Vice Presidents only went on to the Presidency after their chief’s death. And no V.P. who assumed the office was elected again of his own accord.

The Vice Presidency was a kick upstairs, all right.

But the Republican machinery, the convention delegates, and even TR’s fears of a William Jennings Bryan Presidency, all pushed one of the most vocal Republicans into one of the quietest posts in the country.

Even Presidents have some unhappy jobs on their resumé.

But fortunately for Roosevelt, this perfect storm did not track to anonymity.