The big turning points in its tumultuous history

Fifteen years? It feels more like 15 centuries. 

Stand in the raging torrent known as the timeline, surrounded by tweets that will delight and distract and infuriate you, and it’s hard to believe this mighty river ever came from a tiny trickle — much less that the trickle began a mere decade and a half ago. 

But that’s exactly how much time has passed since Jack Dorsey, an unknown engineer at a San Francisco podcasting startup, typed his first words into its experimental texting service, twttr, on March 21, 2006: “Inviting coworkers.” (The famous “just setting up my twttr” was an automated tweet.)  

You might well have guessed the vowels that would soon be added to that very 2006-vintage name. You would never have guessed that, just shy of 15 years later, Jack would be permanently banning a president of the United States who invited a violent insurrection on the same service.

How did we get from there to here? The history of Twitter, age 15, is almost too dramatically improbable to be contained in one article. There’s enough backstabbing and sobbing and unintended consequences for a dozen telenovelas. But here we’ve broken it down into 15 major milestones that — like @Jack’s first tweet — portended so much more than we knew at the time.  

1. When Jack met Ev (and Noah, and Biz, and Crystal, and …) 

The true story of Twitter’s founding would be one of the major bones of contention in the power struggle that consumed the first half of its life. Jack, as the ultimate victor of that struggle, got to rewrite history — to the point where Twitter users might easily imagine the service sprung fully formed from his head. (In later interviews, Dorsey said it came from an idea he had in his childhood.)  

In fact, the Twitter story (as related in Nick Bilton’s comprehensive book based on interviews with all the founders, Hatching Twitter) really starts with Ev Williams, the shy Nebraska-born coder who created Blogger and sold it to Google for tens of millions of dollars. Ev then funded Odeo, a podcasting startup belonging to his friend Noah Glass, and took over as CEO when Noah was floundering. One of Ev’s first engineering hires was Jack, an even more shy coder kid with a nose ring and blue hair. 

When Apple added podcasts to iTunes, Odeo was left without a business model. Jack and Noah got drunk one night; Jack wanted to quit and go into the fashion industry. Only then did Noah tease out of him the idea — Jack was always spitting out ideas — for a service called “Status,” inspired by the status message on LiveJournal blogs as well as by SMS. In Jack’s conception, your status would disappear as soon as you wrote a new one. Call it a proto-Snapchat for words. 

Turning Status into Twitter required all hands on deck. Noah came up with the name, after considering but rejecting Twitch (!) and going forward in the dictionary from there, as well as the timestamp. Ev and his trusty lieutenant Biz Stone insisted that the messages remain (unless users deleted them) in a reverse-chronological timeline, like a blog. Ev coded up some practice tweets before Jack, hacking the thing together with Biz, sent his first. Jack and Biz hold the patent; Jack, Biz, Noah and Ev are officially co-founders.  

Then there were less obvious contributions. Like early employee Crystal Taylor, whom Jack was infatuated with: He’d never used SMS until she showed him how. Contractor Florian Weber did a lot of the early coding. And lest we forget, it was Twitter’s early users — not its creators — who came up with the “@” symbol and the hashtag. “Group effort” is so overused in business that it has become a platitude. But with Twitter, it genuinely applies.    

2. Quake! 

Whenever a temblor strikes, West Coast Twitter reacts like a hive of bees. We hunt the location and magnitude, we comfort each other with dumb jokes, and yes, as Mashable first noted in 2007, we compete to see who tweeted first. (I’m still stupidly proud of the time in 2014 I was dubbed “fastest fingers,” beating MC Hammer.) 

All of this could be seen during the first quake to strike during Twitter’s life, a magnitude 4.5 centered in Santa Rosa on August 2, 2006. Ev had the fastest fingers that time, beating Jack by a minute. Their tweets are time capsules of how they viewed Twitter at the time, as well as their personalities. Ev, who saw Twitter primarily as a newsy microblogging service on the browser, asked if anyone else felt it. Jack, who was all about egocentric status updates via mobile, insisted he alone had.          

Ev won this round, as the earthquake made it obvious to all at Odeo (soon to change its name to Obvious, then Twitter, Inc.) that Twitter was most useful in a breaking news situation. It leveled the playing field between the CNNs of the world and the citizen journalists. “Push-button publishing for the people” was Ev’s slogan for Blogger, but it fitted Twitter better. 

Suddenly news was all about speed and shared experience, and you were only as good as your timestamp. Pretty soon major events worldwide would start breaking on Twitter, from the 2009 “miracle on the Hudson” to the 2011 killing of Osama bin Laden (which leaked via tweets from a guy who heard the Seal Team 6 helicopters.)   

3. SXSW and Steve Jobs

After proving its chops as a news service, Twitter went on to prove it could be surprisingly useful at events, too. South by Southwest in Austin, in March 2007, was its coming-out party. Ev had decked the halls with large screens and posters telling attendees how to sign up, and suddenly it felt like everyone was on it — even though Twitter’s servers were creaking under the strain. It was just too damn useful, more so than the official event guide, for telling people where the hot panels and parties were. When Twitter won “best startup” at the tech conference, it came as no surprise. 

Though Apple’s iPhone launch was still months away, the device that SXSW influencers jokingly called “the Jesus phone” was on everyone’s mind. They were primed to download the first Twitter app, a third-party program called Tweetie (later acquired by Twitter), the following year. The smartphone revolution Steve Jobs wrought would turn out to be perfect timing for Twitter. Its timeline and a screen you could swipe were a match made in heaven (or, depending on the day, the bad place). 

4. Ev takes the wheel

The twin original sins of Twitter both resided in Ev Williams. He was extremely conflict-averse, and also extremely reluctant to lead. But everyone else who could lead was doing an even worse job. Noah was making a hash of Odeo’s operations, so Ev took the CEO role to protect his investment; still Noah acted like he ran the place. When Twitter happened, Noah wanted to run it himself, pissing off Jack and Biz and almost everyone at the startup in the process. Before SXSW 2007, Ev fired him, beginning the myth of the “forgotten founder.”  

Ev then tapped Jack for CEO, figuring the inexperienced programmer could be groomed and grow into the role. But it soon became clear that Jack’s heart wasn’t in the daily grind of running a company. He did nothing about the outages plaguing Twitter — the “fail whale” was famous as early as 2008 — not even when it was discovered the entire site’s database had no backup. He left early for fashion design classes, and was obsessed with tweaking Twitter’s design too. Still, friends like Biz defended his title. 

So with the help of Twitter’s early investors, Ev engineered a boardroom coup that was way more cloak-and-dagger than it needed to be. The VCs fired Jack over breakfast while Ev invited managers to his apartment to drop the news. Crucially, Jack was left with what was supposed to be a ceremonial “silent chairman” role on the board, because Ev felt bad for his former friend.

This all set a pattern for non-communicative drama, driven by fragile male egos, that would persist at the company for years. Hatching Twitter is a litany of mistaken reply-all emails and half-baked leadership plots launched before all the plotters were sure what was going on. The VCs and leadership coaches were just as bad at it as the founders. Mark Zuckerberg was not wrong when he called Twitter “a clown car that fell into a gold mine.”

5. Nobody’s buying

Zuckerberg had reason to be incensed at Twitter when Jack was ousted as CEO: He was on the edge of persuading him to sell the company to Facebook. He would try several more times in the following years with bids as high as $100 million. Ev was willing to listen, but didn’t budge. Nor would he move, in the earliest days, for a $16 million offer from Yahoo, or for any other offer from companies desperate to buy the buzzy service. 

Celebrities like Sean “Diddy” Combs and Ashton Kutcher also tried to schmooze their way into a major stake in Twitter. Al Gore got Ev and Biz drunk one evening in his San Francisco penthouse suite and pitched Twitter TV, a collaboration with his company, Current TV. To Ev’s credit, he turned them all down. 

Twitter would make many blunders; Ev’s favorite poster in the office read “Let’s make better mistakes tomorrow.” But it would not replicate the major mistake of Reddit, which sold out too soon for too little, and lost all its founders at a crucial early juncture in its first 15 years.   

6. Ashton and Oprah …

Though it wasn’t selling out to celebrities, Twitter was swimming in attention from them. In April 2009, Kutcher challenged CNN to a race: Who would own the first Twitter account with a million followers? The answer, despite Anderson Cooper’s best efforts, was Kutcher, who claimed victory on the Oprah Winfrey show. On that same episode, Ev had flown to Chicago to help Oprah send her first tweet. 

Blessed by the queen of TV, Twitter was now a fully mainstream phenomenon. Celebrities were in the ascendancy. Twitter moved to protect them with the now-infamous “blue check,” also introduced in 2009, confirming that they were for real and not one of the numerous parody accounts already on the service. The first verified account wasn’t a celebrity, however, but the CDC; the blue check wouldn’t necessarily help it against a torrent of Twitter misinformation during a pandemic 11 years later.

7. … and Trump. 

In the movie of Twitter’s improbable life, the camera would pan down from Ev’s room for the night in Chicago to reveal that it was in the Trump Hotel. Over ominous music, we would then cut to two weeks later, May 4, 2009. That’s when the Apprentice star’s account, @realdonaldtrump, set up in March, sent its first ever tweet. It looks surprisingly bland to our eyes, but was also vintage Trump. It was about a media appearance, and mentioned Donald Trump in the third person. 

Trump likely didn’t tweet from the account himself until July 2011, which is also when it became hyper-political. Trump thanked fans who were trying to persuade him to run for president. He declined, but also started lambasting President Obama. Amazingly, when Trump first lent his voice to the extreme-right “birther” attacks on Obama in March 2011, he didn’t tweet about it. Later that year he started posting tweets about Obama’s college transcripts and other insinuations — right around the time of Twitter’s town hall with Obama that July.

Most ominously of all, when Trump started lying his face off by spreading a conspiracy theory with obvious racial overtones, no one at Twitter batted an eyelid. This hands-off approach would come back to bite them — and, indeed, the entire world.

8. It’s not easy going green

Back in 2009, Twitter was more focused on retiring its fail whale than the state of the world. So management barely noticed that June when Twitter users started putting a green filter over their profile photos in solidarity with the “green movement” protesting the fraudulent re-election of President Ahmadinejad in Iran. Ev and co were laser-focused on a planned outage that would help move the creaking service to new servers. 

But the State Department noticed that this nighttime downtime would coincide with daytime in Tehran, taking protesters offline just as they were using Twitter to share photos and videos of brutal police repression. So a source at State asked Biz and Ev (via Jack, who had recently gone on a State-sponsored trip to Iraq) to delay the scheduled maintenance. Team Twitter agreed.

But the agreement was reluctant, especially on Biz’s part. Biz saw himself as the moral guardian of Twitter, and normally insisted on political neutrality — even in the case of an obvious dictatorship like Iran. “We are not standing with or against the protesters,” he said internally at the time. Twitter would eventually learn that in times of moral crisis, it is near impossible to stay neutral. 

9. Chairman Jack plays the long game      

Like Noah, the founder who had left quietly, Jack was devastated by his demotion. Unlike Noah, he cooked up a scheme for revenge against Ev. Ironically for someone supposed to be a “silent” chair of the board, Jack would not stop talking to the media. He began spreading the myth that he was still largely responsible for day-to-day decision-making, and that he alone had birthed Twitter. And Ev let him, reasoning that firing Jack outright would just create more unnecessary drama. 

At the same time, Jack began an internal whisper campaign against Ev. In casual chats, Jack encouraged managers to go directly over Ev’s head, to the investors who were still very hands-on, with any concerns they might have about the CEO. Ev, focused on fixing the product, was oblivious to all this. He assumed the board still saw Jack the same way as they did when they fired him in 2008. In fact, they were being seduced by Jack’s media image as much as anyone.

Perhaps the most telling shift came when Jack started imitating Steve Jobs — quite literally, using phrases and adjectives favored by Jobs, adopting his own jeans-based “uniform.” This was partly a function of the fact that there was a Jobs-sized hole in the tech media starting in 2009, when the Apple founder’s health began to worsen. But it did not  escape attention that Jobs was a role model in another way: He was the most famous example of a founder returning to the company he built, ousting pretenders to his throne.      

10. Dick undermines CEO, consolidates power

Dick Costolo was a standup comedian as well as a tech wizard. So after his friend Ev hired him as a grown-up COO in 2009, it wasn’t surprising that Dick’s first tweet at the company pretended to allude to a boardroom coup that would put him in charge. Dick genuinely liked Ev; he didn’t mean it. 

So it was all the more surprising one year later, in October 2010, when Dick took part in a boardroom coup that put him in charge and brought Jack back in a day-to-day role. Dick was still attempting to do right by Ev, and at one point tried to announce his resignation rather than take over. The board wouldn’t let him. The phrase “shitshow” barely begins to cover the story of Dick’s ascension.

Still, he remained CEO for five years until Jack took over, and was more perceptive about the main problem haunting Twitter than either the founder who preceded him or the one who followed him. “We suck at dealing with abuse and trolls on the platform and we’ve sucked at it for years,” Dick wrote in an internal memo in 2015, at the height of Gamergate’s misogynistic targeted harassment. “We lose core user after core user by not addressing simple trolling issues that they face every day.”  

Dick added that he was “ashamed” and took “full responsibility,” and that a plan of “kicking these people right off” would begin soon. Instead, he left Twitter several months later. The company’s IPO had been initially successful, but Wall Street was unhappy with the dismal performance of Twitter stock since then. (It performed poorly until mid-2020, and still isn’t in the same realm as other tech stocks — in part due to Twitter’s reputation for hosting trolls.) 

11. The Dickbar and the blue lines

Twitter continued to experiment with new revenue streams in the Dick era. Promoted tweets, planned as early as 2010, started to proliferate, as did promoted trends. One experiment went too far for most users; it was called the Quick Bar, a promoted trend in a gray box that constantly hovered at the top of Twitter.com. Users started calling it the “Dickbar.” It was quietly dropped.

Then came the blue lines that connected tweets in a conversation in the timeline (they were already connected if you clicked on the tweet itself. How we hated the blue lines at first! Except it actually turned out to be quite useful for tweets to be automatically connected — or threaded — especially for newcomers to the service. The days of the multi-part mega-thread had begun. Sometimes, Twitter actually knew what it was doing.  

12. The Ellen selfie

It has long since been surpassed as the most-liked tweet in history; these days it isn’t even in the top 30. But the Ellen selfie at the 2014 Oscars (actually taken by Bradley Cooper, lest we forget) was something of a high water mark for the celebrity culture of Twitter, when it formed an inextricable bond with a major entertainment event. 

Look at those innocent smiles from a bygone age, before the Trump era, before the Moonlight/La-la Land debacle, before selfies were considered gauche. And before a certain hashtag came along to sweep one of those celebrities (Kevin Spacey, top row center) out of Hollywood for good. We’ll never see it the same way again. 

13. #MeToo

“Me Too” as a phrase used to surface sexual abuse and harassment dates back to activist Tarana Burke, who used it on MySpace in 2006. But it became inextricably linked to Twitter — and gained the hashtag — in October 2017. Harvey Weinstein had just been unmasked as the most loathsome predator in films, but it was clear that he was just the tip of an evil iceberg that could do with way more light and heat. 

So actor Alyssa Milano had a suggestion from a friend to share with her millions of followers. (Surprisingly, it didn’t contain the now-ubiquitous hashtag.) More than 80,000 responses later, a global movement had arrived, the sheer size and scope of which dwarfed the trolls of Gamergate. There were more than 19 million #MeToo tweets in the next year. Men who were prepared to listen and to help started hashtags of their own, such as #IDidThat and #IWill. For all of Twitter’s association with pro-democracy protests, this feels like the most long-lasting revolution in its history.

14. Trump tagged, Trump banned

There are too many milestones in the hideous history of Trump’s Twitter usage to recount here. There were 57,000 tweets from @realdonaldtrump in total, just under half of them during his presidency. They contained thousands of insults and straight-up lies, hundreds of retweeted conspiracy theories, dozens of personal attacks and barely veiled racist tweets that should have run afoul of Twitter’s terms of service, a couple of threats of war, and one “covfefe.”

Still, Jack refused to touch Trump’s account, citing the public interest in letting a president tweet whatever he wanted. Not until May 2020 did Twitter tentatively add its first “fact-check” link to a Trump tweet about a “rigged election.” A “public interest notice” was added when Trump used the phrase “when the looting starts, the shooting starts” in reference to Black Lives Matters protests. All of it was woefully inadequate, and only drove Trump to new lows of whiny victimhood.

On the day of the Capitol attack, January 6, 2021, Twitter locked Trump’s account, and deleted it for good two days later, along with tens of thousands of QAnon accounts. Jack worried about the precedent he was setting. But misinformation about election fraud on social media plummeted by nearly three-quarters that week, and the vast majority of Twitter users breathed a sigh of relief as the service suddenly became a more civil place.   

15. Obama, Biden, and Harris win Twitter

When Trump’s account went to Twitter hell, it had 88 million followers. That paled in comparison with the 130 million followers of Twitter’s most-followed account, @BarackObama. (Trump also never surpassed Lady Gaga, Taylor Swift, Cristiano Ronaldo, Rihanna, Katy Perry, or Justin Bieber.) After all that sound and fury, after four years of attempting to erase Obama’s legacy, Trump could not touch his nemesis on Twitter. 

Trump also never had anything that rated as a “most liked” tweet (the announcement of his coronavirus diagnosis came closest, with 1.6 million likes). At time of writing, the record is held by the announcement of Chadwick Boseman’s untimely death in August 2020, with 7.4 million likes (which tells us Twitter should probably consider allowing different emotions as alternatives, Facebook-style).  

But look at the tweets that round out the top 10 most-liked. Number 2 is Joe Biden’s “It’s a new day in America” from Inauguration Day 2021. Then it’s two from the post-presidency of his old boss Obama, and a couple more from the Biden team on November 7, 2020, including Kamala Harris’ famous “we did it” phone call from the day the election was called, November 7, 2020. 

It’s a new day on Twitter, too. We can only hope that as the site barrels towards its 16th birthday that its teenage growing pains are mostly behind us.