Few stories in 2022 have captivated the public's attention like Elon Musk buying Twitter. Musk brings with him more drama than a yacht ride with Jennifer Coolidge. It all started in early April, when Musk's big chunk of Twitter stock was announced; later that month he said to heck with it—he’ll just buy the whole thing.

On April 14, Musk came in with a cheeky buyout offer to take Twitter private at $54.20 a share, or about $44 billion. Get it? “420” in the share offer? That’s the universal number for weed. Hilarity didn’t stop there for the billionaire jester.

On Oct. 26, Musk strolled into his newly bought Twitter HQ carrying a sink. “Let that sink in,” he tweeted with a video of the moment. Later he would tweet: “Comedy is now legal on Twitter,” which encapsulated why he bought Twitter—to give permission to accounts he found amusing to have more freedom, sticking it to any scolds who might object on the basis that some of the newly restored accounts had once been banned for hateful speech or harassment.

It wasn’t quite so funny for advertisers, and there has been an exodus of major brands flying off Twitter, worried that Musk's policies could make the service less predictable. There have been activist protests, claiming Musk’s loose moderation gave an opening to hate-mongers. Musk has disputed those attacks from groups he considers “woke” hall monitors. There also has been a massive reduction in workers at Twitter, casualties of Musk’s purge and his demands for “hardcore” work commitments. And it has all played out on Twitter, where Musk has more than 120 million followers ostensibly hanging on his every tweet.

Look back: Brand reactions to Elon Musk and Twitter

Here is a look at some of the most noteworthy moments, so far, and how Musk’s Twitter experiment turned into the biggest advertising story of the year.

Oct. 4

Despite trying to back out of buying Twitter, even suing to halt the deal, the reality was Musk's $44 billion offer from April was set in stone. So, Musk accepts the inevitability and paints an optimistic picture of his plans to turn Twitter into a super app.

Oct. 26

The conquering hero enters his new domain for the first time, with the now-famous dad joke, “Let that sink in.”

Oct. 27

Musk gives his first official statement to Twitter advertisers, assuring them nothing much will change. This place won’t turn into a “hellscape.”

Musk also proclaims that the “bird is freed,” suggesting he also still is committed to his more permissive policies, which prompted him to buy Twitter in the first place.

Oct. 28

But Musk’s second order of business is to help Catturd, an enigmatic, possibly trollish, account find out why it’s been “shadowbanned,” a term that means the account had some action taken against it by previous moderators. Musk promises to handle it.

Musk also makes a promise that comes back to haunt him with advertisers, claiming there will be a content moderation panel making key decisions, presumably around things like what to do with “Catturd” and more prominent accounts.

Musk also gets a kick out of some real-life trolls who pretend to be two laid-off Twitter employees outside the San Francisco HQ, who give the names “Ligma” and “Johnson” to the media. Musk would call it one of the best trolls ever.

Oct. 29

There are signs of trouble, though, for brand safety. Powerful NBA star and media mogul LeBron James tweets about concerns over a rise in hate speech on Twitter in Musk’s first days at the helm.

Oct. 30

Musk tweets at former Secretary of State Hillary Clinton. Musk was replying to Clinton’s tweet about the home-invasion attack on Nancy Pelosi’s husband, and Musk implied the assault could have been part of a conspiracy, which echoed some right-wing misinformation. Musk later deleted the tweet, but as it came just days after he took over Twitter, the fact Musk was retweeting dubious conspiracies reinforced brands’ concerns about his commitment to combating misinformation.

Nov. 2

Musk meets with the NAACP and other civil rights organizations that were concerned about those reports of a spike in slurs on Twitter. The meeting came the day after the first inkling of a brand exodus started forming. IPG’s Mediabrands sent a note to clients on Nov. 1 advising brands to pause ads on Twitter until moderation policies became clearer. The week prior General Motors had publicly paused ads—it is an automaker and Musk owns Tesla, a rival carmaker. 

Nov. 4

It’s a turning point day for Twitter and its ad fortunes under Musk. Sarah Personette, the chief customer officer, who seemed to be going along with the transition, abruptly leaves the company. JP Maheu, global head of client solutions, also left, and the ranks of brand allies seemed to be growing thinner at Twitter. One major marketer, who worked closely with Maheu, said Maheu’s exit was like a “public hanging” as he was unceremoniously shown the door. Musk had been purging Twitter staff, which stood at about 7,500 people before he took over. Since then, Twitter's workforce is fewer than half that. The lack of staff has been a concern for advertisers: “You’re getting rid of everyone who can calm the market and it’s not going well,” one major advertising exec, and top Twitter advertiser, told Ad Age in November. Major brands including Mondelēz, General Mills and others started backing away from Twitter.

Musk acknowledges the advertising woes in a tweet. And then Musk responds to another tweeter that he will “name and shame” brands that pull back.

Nov. 7

Musk seems to be cool with how it’s going so far—all according to plan.

Nov. 10

A brand issue arises after Musk decides to sell “blue checks” as part of an $8 monthly subscription plan. The revenue opportunity backfired because any account could use those verification checks to impersonate brands, and they did, trolling brands including Pepsi, Nintendo and Eli Lilly. Musk had to pause his “blue check” program and retooled it with more safeguards in December. On Nov. 11, Musk tweeted that one new policy would mean any parody accounts had to clearly say they were just kidding. It was a little late for some brands, as another major holding company, Omnicom Media Group, sent an advisory to clients to consider pausing their Twitter ads while the service seemed unsafe.

Nov. 17

Today is the day that the remaining Twitter employees have to commit to “hardcore” grinding hours, or just leave. Many so-called “tweeps” pick the exit, sharing their goodbyes on Twitter under the hashtag “love where you worked” and waving a saluting emoji in tweets. On Nov. 18, Robin Wheeler, who stepped in for Personette and Maheu, leaves Twitter, also tweeting a saluting emoji. Chris Riedy would ascend to the role of top ad leader at Twitter.

An Ad Age analysis of Twitter’s top advertisers shows that major brands, indeed, are pulling back from spending on the platform. Pathmatics, a digital advertising analytics firm, shows that the top spenders on Twitter have gone from major brands like Warner Bros. Discovery to lower-quality websites and retailers. Macy’s, which had been preparing for holiday shopping campaigns, told Ad Age that it completely paused advertising on Twitter amid the ongoing concerns about Musk.

Nov. 19

“Vox Populi, Vox Dei,” Musk tweets, claiming the people had spoken, as he makes perhaps the biggest moderation policy change since he took over: unbanning former President Donald Trump. Some critics in the advertising world were concerned about the procedure Musk used to make the content and moderation decisions, which seemed to violate his promise to consult a moderation council before making major changes.

Nov. 23

Musk again turns to a Twitter poll to make a moderation decision, this time asking if he should unban accounts under a general amnesty, paving the way for all manner of accounts to rejoin, including those of alleged neo-Nazis. The Washington Post would later report that ads from major brands were appearing alongside potentially objectionable material on the profile accounts of reinstated tweeters.

Nov. 26

Musk tweets a retort to potential critics by sharing slides that claim to show hate speech is down on Twitter, while activity is up. Advertisers, however, have been skeptical about claims that Twitter has made under Musk's leadership, because of a lack of independent verification. There also have been layoffs among Twitter teams that used to work with advertisers to explain data and analytics around measurement and brand safety, Ad Age reported.

Nov. 28

Musk picks a public tiff with Apple, one of the largest advertisers on Twitter, claiming that the iPhone maker threatened to kick Twitter off the App Store. Musk also said Apple mostly stopped advertising on Twitter.

Nov. 30

Twitter’s business account posts a blog post link to Twitter, explaining “Twitter 2.0.” The blog post describes how “none of our policies have changed.” However, the prior day Twitter had made new rules around moderating content related to COVID, and advertisers were concerned that Twitter’s public policy stances, such as saying no policies changed, did not match reality.

At least the crisis with Apple appeared to have been averted as Musk tweeted from Cupertino that day, too, saying he had a productive chat with Apple CEO Tim Cook.

Dec. 2

Musk promotes the first “Twitter files,” which would become popular fodder on the platform after Musk disclosed internal communications from before he bought Twitter. The files were mostly related to content decisions, including how the platform moderated the story around the Hunter Biden laptop during the 2020 election. Critics of Twitter’s pre-Musk moderation claimed the platform was biased against Trump’s campaign. Since then, there have been several disclosures of much-hyped Twitter files.

Dec. 3

Musk and his allies hold a widely attended Twitter Spaces to discuss Twitter files and other topics. About 1.1 million people listen to the Q&A. Musk mentions that advertisers were starting to return to the service, although there are signs that might not be the case: Ad Age reported on surprising last-minute deals that Twitter was offering advertisers, as it was unable to attract the kind of ad dollars it hoped for even the World Cup.

Dec. 12

Musk continues to promote the Twitter files, already up to Part 5.

Dec. 14

Musk bans a Twitter account called @elonjet, and the college student who ran the account, Jack Sweeney. The “elonjet” Twitter account used to post about the travels of Musk’s jet, which Musk never appreciated. He reportedly once tried to buy the account to shut it down. Instead, weeks after buying Twitter, he apparently used his power to silence the jet tracker. Some critics are using the example of censorship to demonstrate that Musk might not be as pro-free speech as he has claimed in his rulemaking at Twitter.

Dec. 18

Musk turns to Twitter polls again, this time for perhaps his biggest request yet, asking the “populi”: “Should I step down as head of Twitter.” There’s a fairly resounding, “yes,” with 57.5% of respondents advising Musk to remove himself as Twitter CEO. The billionaire was clearly considering the move, as there have been reports Musk also was looking for a fresh infusion of money from outside investors. Musk’s decision making, especially around moderation, continued to be questioned, after a round of temporary bans hit prominent journalists, too, including reporters at New York Times and Washington Post. Musk’s Twitter adventures have appeared to harm even his unrelated companies like Tesla, the electric car giant, where the share price dropped more than 60% this year, and Musk’s image as an unstoppable corporate wealth generator has been tainted.