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"Free Helicopter Rides" refers to extrajudicial killings known as "death flights," in which military forces throw people from aircraft into large bodies of water. Online, the phrase is often used by members of the alt-right in jokes about executing their political opponents.
During the Argentine Dirty War from 1976 to 1983, the military reportedly executed an estimated 10,000 people, many of which were thrown out of aircraft into the Rio de la Plata or Atlantic Ocean. Additionally, the practice was also reportedly employed by Chilean dictator Augusto Pinochet, who ruled the country from 1973 to 1990.
On May 29th, 2015, Facebook user Litagano Motscoud posted an image of Pinochet throwing Bernie Sanders from a helicopter with the caption "Is one allowed to dream" (shown below).
On July 31st, 2015, an anonymous 4chan user posted a Bernie Sanders bumper sticker image to the /pol/ (politically incorrect) board, where others replied with offers of free helicopter rides (shown below)
On May 11th, 2016, the donaldtrumpepe Tumblr blog shared an illustration of Pusheen throwing Carl the Cuck out of a helicopter (shown below, left). On May 20th, the blog posted an illustration of Feels Guy being thrown out a Trump helicopter by Pepe the Frog (shown below, right).
On May 24th, YouTuber Very Bad Goyim uploaded a video of Donald Trump saying "let's give them a helicopter ride" followed by a clip showing a fleet of helicopters marked with "Trump" (shown below, left). On June 2nd, the God Emperor Trump channel uploaded a video of the Trump clip followed by edited footage of Hillary Clinton being thrown out of a helicopter (shown below, right).
On June 17th, the feminist blog We Hunted The Mammoth published an article about the helicopter ride meme. On November 5th, FunnyJunk user mortuz submitted a screenshot of a Twitter argument between conservative comedian Steven Crowder and a person named Leah titled "Leah needs a fucking helicopter ride."
 We Hunted The Mammoth – Memeday If Donald Trump offers you a free helicopter ride say no