Alice wasn’t the only Roosevelt child to go his own way. Quentin, the youngest of President Theodore Roosevelt’s kids, was “a fine bad little boy,” as his mother often said. But he was also the leader of the “White House Gang,” a name given to them by the president himself. Growing up in the White House allowed for all sorts of mischief by this gang of rowdy boys, which included future President William Howard Taft’s son and the children of other Washington politicians. With Quentin at the lead, the group carved a baseball diamond into the White House lawn, shot spitballs at the portrait of Andrew Jackson, and even launch “attacks” on other Washington buildings. Quentin once brought 3 snakes, wound around his arms, as he entered the Oval Office on roller skates. According to the New York Times, he skated into the room, where his father was having a meeting with Attorney General Bonaparte, who “hurriedly ascended [climbed] the back of his chair.”
“What’s the matter?” Quentin asked. “Aren’t they lovely snakes?” While Quentin got a rowdy start in life, he eventually calmed down. He attended Harvard University and got engaged to Flora Payne Whitney, the granddaughter of Cornelius Vanderbilt, one of the richest men in the United States at the time. After some time at Harvard, he joined the U.S. Air Service, and died in World War I after his plane was shot down in France.