Quentin Roosevelt - The "fine little bad boy" who brought havoc to the White House - see comments (1906)

Theodore Roosevelt, upon moving into the White House, along with his wife, Edith, were determined that the house would be a home for their children. As such, the kids (Alice, TR Jr, Ethel, Kermit, Archie and Quentin) had the run of the place. Quentin, TR’s youngest son (and arguably his favorite), was an energetic and curious kid who had a way of finding trouble. Among some of this exploits were:

Bringing their pony into the White House and up the elevator to visit his sick brother

Carving a baseball diamond into the south lawn

Running his wagon through a portrait of Mrs. Van Buren

Defacing a portrait of Andrew Jackson by spit-balling a beard on to his image (he got in BIG trouble for this one)

Blinding workers in the executive building with mirrors

Interrupting cabinet meetings, sometimes with live snakes to show his Dad

Breaking a window with a snow ball, then running to the British Embassy and claiming asylum

Dropping snow boulders from the roof of the White House onto the President’s security officers

Joining random meetings of the defense department at the old War Navy building

Buying and selling pigs

Ripping up the grass of Lafayette park by racing his pony

Brokered deals with an ice cream man for free ice cream, by endorsing it to his classmates

Hitting his teacher (accidently) with a giant spitball (for which the President arrived at the school the following day with flowers and an apology)

Quentin went on to join the US Airforce at the onset of WWI and became a skilled pilot. He was known for taking risks and had a couple of close calls before finally being shot down over France. He was a pretty amazing kid.

/r/OldSchoolCool Thread Link - theodore-roosevelt.com