The quest to secure the Medal of Honor for Theodore Roosevelt ended after 103 years when President William J. Clinton presented the nation's highest military award to Theodore Roosevelt posthumously. Tweed Roosevelt received the Medal on behalf of the Roosevelt family, in the Roosevelt Room of the White House on Tuesday, January 16, 2001.
Congressman Paul McHale introduced a bill to give the Medal of Honor to TR in 1996, and then introduced a second bill on July 25, 1997, HR 2263, entitled "A bill to authorize and request the President to award the Congressional Medal of Honor posthumously to Theodore Roosevelt for his gallant and heroic actions in the attack on San Juan Heights, Cuba, during the Spanish-American War." HR 2263 had over 160 co-sponsors in the House of Representatives, forming an impressive and bipartisan coalition. Congressman Rick Lazio, Republican from Brightwaters, Long Island, New York, filed the formal application and supporting evidence with the U.S. Army for the posthumous award. Congressman Steve Buyer, Republican from Indiana, Chairman of the House Military Personnel Subcommittee, greatly helped to rally support for the bill in the House of Representatives.
The opposition to awarding the Medal of Honor to TR came particularly from elements within the U.S. Army. The Army has opposed in general the repeal of the statute of limitations on military decorations and the award of what might be called historical medals. Moreover, some in the Army thought that Roosevelt simply did not deserve the Medal of Honor. While no public statement was made on the case, it is widely believed that some historians in the Army think that TR was no more outstanding than many other brave officers in the battle of July 1, 1898 in Cuba, who did not receive the Medal of Honor either. In any event, while Congressman McHale's bill was making its way through the House in 1998, TR's cause received a major setback when the Senior Army Decorations Board recommended that the Medal of Honor again be denied to TR. TR's supporters, of course, took issue with this ruling.
On October 22, 1998, the day after the bill cleared the Senate, Bill Bleyer reported in Newsday: "In a compromise to placate legislators who did not want to offend the Army, a letter signed by five Senators and Congressmen involved in the issue will accompany the bill to the White House." The letter requested the President to "seek the advice of the secretary of the Army" on the matter, and to ask the Army to "prepare a full and formal record of Theodore Roosevelt's valor." The bill was signed by President Clinton in the Roosevelt Room of the White House on the afternoon of Thursday, November 12, 1998. Among those present were Tweed Roosevelt, Congressman Peter King, the New York Republican whose district includes Sagamore Hill, and Senator Kent Conrad of North Dakota. The President then honored the request from those in Congress who did not want to bypass the Army, and the matter was referred back to the Army for review.
On January 16, 2001, in the Roosevelt Room of the White House, TR's Medal of Honor was given to the Roosevelt family, and at the same time the descendants of Andrew Jackson Smith, a slave who escaped and fought in the Union Army during the Civil War, also received the Medal of Honor for the bravery deeds of their ancestor.