"It is representative of the strange bedfellows that the interaction of the US and Chinese technology systems creates," said Adam Segal, a cybersecurity expert at the Council on Foreign Relations.
"There is much bringing them together — money, people, and ideas. And there are serious political forces pulling them apart."
The deal has sparked a furious reaction on Reddit, as avid users take to the website to post photos exposing China and its firewall before the potential "censorship" starts.
TIANANMEN SQUARE
One user posted a picture of Tiananmen Square, the scene of the 1989 massacre where nearly a million pro-democratic protesters gathered before being indiscriminately fired at by Chinese troops.
TIBET
Another shared a picture of Tibetan protesters being beaten by Chinese soldiers, an image demonstrating the extent to which violence is used to dealt with peaceful resistance to China's rule, something the Great Firewall stops from coming to the public's attention.
HONG KONG
As fears grow over the status of Hong Kong's autonomy and the decline of its self-rule becomes a major concern, protests have become commonplace in the streets on Hong Kong. One user took to Reddit to share their disdain towards the new deal between Reddit and Tencent, and their fear of the website becoming censored.
CONCENTRATION CAMPS
China's 'patriotic' crackdown on religion in an effort to 'Sinicize' their entire culture saw the construction of what they called "re-education" camps in Beijing. But the UN human rights committee and leaked photographs revealed what were really concentration camps where approximately one million Uighurs were being held in arbitrary detention.
Reddit, a company which stands for free speech, isn't alone in receiving a cash booster from the tech juggernaut, with Snap and Discord included in Tencent's global investment program.