Check out more of the 2014 VICE News Awards here.

If this year in social media told us anything, it's that Twitter is lousy with racists, sexists, and confused celebrities who believe a hashtag can rescue terror hostages. In a cyber environment punctuated by trolling and abuse, the worst tweet of 2014 is a fiercely contested prize. One tweet, however, helped color one of the year's highest-profile PR implosions. Uber outdid itself in proving that unbridled libertarian start-up culture does not a healthy sharing economy make.

The car service, it was reported, not only tracks the presumed one-night stands of its users — it also threatens critical journalists, and chose to briefly jack up prices in Sydney during a tragic hostage crisis that left three dead. Arch libertarian Peter Thiel went so far as to call Uber "the most ethically challenged company in Silicon Valley."

With one tweet, Uber investor Jason Calacanis epitomized the sort of white privilege undergirding Silicon Valley culture.

Previously, in 2013, Calacanis took to Twitter to say that racism does not exist in the tech world, and that the only determinant to anyone's success is "hustle." If you want to break into tech journalism, he said you only need to "blog every day for three years." "There isn't a race wall in tech," the blithe bootstraps believer wrote in 2013.

This year, Calacanis doubled down with a fresh kernel of white privilege condensed into a tweet:

@anildash @DrPizza @zigdon that doesn't mean my career was given to me by 'white privilidge' -- that's racist.

— jason (@Jason) July 18, 2014

With hope, and with the help of nationwide protests against police killing and mistreatment of black lives in America, 2014 will stand out as a year in which the brutal truths of ongoing structural racism could not be ignored. One hopes Calacanis and his cadre will spend the holiday period ruminating on the undeniable fact that white privilege, or "privilidge" if he insists, indeed played a role in his gratuitous success.

Other dishonorable mentions in this category:

While the hashtag #MyNYPD, launched by the police department in an epic backfire of a PR stunt, produced some of the year's finest tweets in response, highlighting multiple instances of police abuse, the original tweet from the NYPD's account deserves mention for its lacking self-awareness and dissonance with our political moment.

Do you have a photo w/ a member of the NYPD? Tweet us & tag it #myNYPD. It may be featured on our Facebook. pic.twitter.com/mE2c3oSmm6

— NYPD NEWS (@NYPDnews) April 22, 2014

"And we're going to have to run you over, just for good measure." #myNYPD pic.twitter.com/q6JMNAajxb

— Casey Aldridge (@CaseyJAldridge) April 22, 2014

An equally notable failure came from Bill Cosby, who posted a picture of himself to Twitter and asked his followers to "Meme me" — just as news began to break about the multiple claims of sexual assault against the comedian.

#CosbyMeme Oh Boy! pic.twitter.com/5shOSuH74c

— E.J. Coughlin (@ejc) November 10, 2014

Don't mind if I do… #CosbyMeme pic.twitter.com/vdS2icWEHD

— Rusty Redenbacher (@rustymk2) November 10, 2014

And our final dishonorable mention goes to Office of Federal Student Aid (FAFSA), which tweeted, and then apologized for, a message with an image of Kristen Wig's character in comedy Bridesmaids drunkenly pleading "Help me. I'm Poor." "If this is you, better fill out your FAFSA," tweeted the federal office, in a tasteless joke, which was rightly read as an offensive jab at low-income students.

Fail.

This article has been updated since it was initially published. The author described Uber investor Jason Calacanis as a "billionaire" when his net worth is estimated to be significantly less.

Follow Natasha Lennard on Twitter: @natashalennard