Sixteen years after Platt's resignation, he was elected a second time as a
U.S. Senator from New York in
January 1897 and was re-elected in
January 1903. This time, he served from March 4, 1897, to March 3, 1909. He was Chairman of the Committee on Transportation Routes to the Seaboard (in the 55th Congress). He was on the Committee on Printing (in the 56th through 60th Congresses), the Committee on Cuban Relations (in the 59th Congress) and the Committee on Interoceanic Canals (in the 59th Congress). He also served on the
Republican National Committee. On January 21, 1897, Platt's photograph appeared in the
New York Tribune as "the first
halftone reproduction to appear in a mass circulation daily paper," according to Time-Life's
Photojournalism. To increase his power as a
political boss, Platt steered passage of the Greater New York bill in 1898. The bill incorporated the boroughs of
Brooklyn,
Queens, and
Staten Island into the city, thereby creating New York City as it exists today. Platt reluctantly supported Theodore Roosevelt's candidacy for
Governor of New York in 1898 in the immediate aftermath of Roosevelt's fame leading the
Rough Riders in the
Spanish–American War earlier that year. Once elected, Governor Roosevelt was independently minded and crusaded against machines and corruption, most notably refusing to reappoint
Louis F. Payn as state Insurance Superintendent because he was widely seen as a corrupt associate of Platt. In response, Platt sought a way to "shelve" Roosevelt so that a more compliant governor could be installed in his place. President
William McKinley's original vice president had died in office, leaving a place on the ticket to fill before the 1900 election. At the
1900 Republican National Convention, Platt and
Matthew Quay proposed to get Roosevelt out of Platt's way in New York by nominating him for vice president. Party boss
Mark Hanna was horrified by the proposition, stating "Why, everybody's gone crazy! What is the matter with all of you? Here's this convention going headlong for Roosevelt for Vice President. Don't any of you realize that there's only one life between that madman and the Presidency? Platt and Quay are no better than idiots! What harm can he do as Governor of New York compared to the damage he will do as President if McKinley should die?" But since Hanna was unable to convince President McKinley to refuse Roosevelt as his Vice President, his efforts were in vain. Roosevelt was chosen by acclamation, played a major part in McKinley's re-election, and became president in September 1901 after McKinley was assassinated in office. Platt's control over the Republican Party in New York State effectively ended in 1902.
Benjamin Barker Odell Jr., Roosevelt's successor as governor, had not only acted independently of Platt but also, by 1902, insisted on taking over from Platt as leader of the party. After Platt tried but failed to block Odell's renomination as governor and Odell was re-elected, the era of a separate "boss" was over. Platt was a member of the New York
Society of Colonial Wars. ==Later years, death, and legacy==