Elon Musk has fired Twitter CEO Parag Agrawal. From blunt text messages and clashes over bots to lawsuits and a poop emoji, here's a history of their relationship.

Tesla and SpaceX CEO Elon Musk started buying Twitter stock on an almost-daily basis in January.

By the spring, Musk had accumulated a 9.2% share in Twitter, making him its biggest shareholder. Shortly after, it was revealed that Musk was going to join its board.

Messages between Musk and Agrawal were released in September as part of a lawsuit Twitter filed against Musk.

"Hey Elon - great to be connected directly. Would love to chat," Agrawal said in a message to Musk on March 27.

Musk, Agrawal, and Twitter chair Bret Taylor met for a meal near San Jose on March 31.

"Great dinner :)," Musk messaged after.

"Memorable for multiple reasons," Agrawal texted. "Really enjoyed it."

"I'm super excited about the opportunity and look forward to working closely and finding ways to use your time as effectively as possible to improve Twitter and the public conversation," Agrawal texted on April 3.

Agrawal announced publicly that Musk was joining the board in a tweet on April 5, saying that Musk was "both a passionate believer and intense critic of the service which is exactly what we need on @Twitter, and in the boardroom, to make us stronger in the long-term."

On April 7, Agrawal asked Musk to speak to Twitter staff and answer questions on "the future of Twitter and why it matters." He warned Musk that there would also be some questions "from people who are upset that you are involved and generally don't like you for some reason."

"I think there is a large silent majority that is excited about you bring [sic] on the board," Agrawal later added.

Musk texted Agrawal saying that he had "ton of ideas" for the platform, and Agrawal seemed eager to listen.

"I want to hear all the ideas — and I'll tell you which ones I'll make progress on," Agrawal responded.

It didn't take long for the relationship to sour.

Musk tweeted on April 9 that some of Twitter's most-followed accounts "tweet rarely and post very little content." "Is Twitter dying?" he asked.

Agrawal understandably didn't like the tweet.

"You are free to tweet 'is Twitter dying?' or anything else about Twitter — but it's my responsibility to tell you that it's not helping me make Twitter better in the current context," Agrawal texted Musk later that day.

"What did you get done this week?" Musk replied less than two minutes later in a string of texts. "I'm not joining the board. This is a waste of time. Will make an offer to take Twitter private."

"Can we talk?" Agrawal replied. Musk didn't appear to respond to him, per the message logs published as part of the lawsuit, but he did reply to a message from Taylor and told him that Twitter needed "drastic action."

Two days after those messages were sent, Agrawal announced that Musk would no longer be joining the board.

"I believe this is for the best," Agrawal said.

Musk made an offer to buy Twitter for $54.20 a share in cash, a Securities and Exchange Commission filing on April 13 revealed.

In the filing, Musk showed his lack of support for Agrawal's leadership.

"If the deal doesn't work, given that I don't have confidence in management nor do I believe I can drive the necessary change in the public market, I would need to reconsider my position as a shareholder," he wrote in the filing.

Without the changes Musk sought, Twitter was "simply not a good investment," he wrote.

Twitter agreed to the deal on April 25.

Former Twitter CEO Jack Dorsey acted as a mediator during a phone call between Agrawal and Musk on April 26.

Musk texted Dorsey afterwards, saying that Agrawal was "moving far too slowly and trying to please people who will not be happy no matter what he does."

"At least it became clear that you can't work together," Dorsey replied. "That was clarifying."

Musk texted Agrawal Twitter CFO Ned Segal on June 28 after they requested information about the status of Musk's financing for the deal.

"Your lawyers are using these conversations to cause trouble," Musk texted, legal filings reveal. "That needs to stop."

Musk has repeatedly expressed concerns about the number of bot accounts on the platform.

In May, Musk appeared to be hesitant about the Twitter deal, tweeting that he'd put it "on hold" until Twitter gave him more data related to the number of bots on the platform. He also told his lawyers to "slow down" the deal, text messages show.

Twitter says bots make up less than 5% of the platform's 238 million monetized daily active users. Research by the digital-intelligence provider Similarweb backs up these claims, but found that because these accounts tweet so much, between 20% and 29% of US Twitter content is generated by spam accounts.

Agrawal posted a thread on Twitter explaining why Musk's plan to survey the number of bots on the platform was flawed. Musk responded to the thread with a poop emoji.

In July, Musk sent a letter to Twitter terminating the deal, claiming that the social-media giant had withheld or distorted data on the number of bot accounts on the platform.

In some cases Twitter had refused to share data, while in others it gave him "incomplete or unusable information," Musk's lawyers said.

Within days of Musk terminating the deal, Twitter sued him to force him to complete the deal, accusing him of "refusing to honor his obligations."

Musk countersued later in July, alleging that the company intentionally miscounted the number of spam accounts as part of what he called "its scheme to mislead investors about the company's prospects."

In August, Musk called on Agrawal to take part in a "public debate" about the percentage of bots on the platform.

"Let him prove to the public that Twitter has <5% fake or spam daily users!," Musk wrote.

After months of Musk trying to abandon the deal, his lawyers sent Twitter a letter renewing the original offer on October 4.

Musk and Twitter came close to agreeing a deal at a roughly 8% discount for the tech mogul, sources told Insider.

But the talks fell through after the two sides clashed, with Musk's attorney saying that Twitter's executives and board wanted "all kinds of things" in the renegotiated deal that the billionaire refused to accept.

The deal final went through on Thursday evening, just hours before the October 28 deadline given to Musk by court.

One of the tech mogul's first moves was to fire Agrawal. The same evening, Musk also ousted CFO Ned Segal, chief legal officer Vijaya Gadde, and general counsel Sean Edgett, sources told Insider.