A CALL WITH JACK: How Twitter CEO, Jack Dorsey, restricted advertising for Trump’s campaign

Gary Coby
Gary Coby
Nov 18, 2016 · 6 min read

On Sunday, I tweeted…

We had an “upfront deal” with Twitter, which is a common setup where we commit to spending a certain amount on advertising and in exchange receive discounts, perks, and custom solutions.

Our upfront deal was signed in August.

Deal Highlights:

  • $5MM Spend Commitment
  • Discounts on Promoted Trends
  • Bonus Media on Other Spending
  • Value Adds, such as Custom Hashtag Emojis

We also had several promoted trends reserved/purchased:

  • 7/21 RNC Day 4
  • 9/26 1st Debate
  • 10/9 2nd Debate
  • 11/5 Sun Before Election Day


Twitter — or well, Dorsey — restricted us on the most unique part of our deal, the custom hashtag emojis, of which we had two.

It’s an emoji tied to a specific hashtag. When anyone uses that hashtag, the emoji is automatically added at the end.

We planned to launch both of our emojis for the first debate. One was a contrasting emoji for the popular #CrookedHillary. They were going to be featured in our promoted trend for maximum exposure.


At the beginning of September, I outlined several possible emoji concepts for the TW creative team to make.

About 2 weeks before the 9/26 debate, the TW team provided several designs that were pre-approved by their legal and policy teams. One included was a hand receiving a moneybag:

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Emoji originally designed and approved by Twitter to be used with #CrookedHillary

Next, I met with TW in NY, at Trump Tower, to tweak the already approved emoji designs. Pushing the envelope, the hand/moneybag emoji evolved into a running stick figure with a moneybag:

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Evolution of the already approved “hand w/ moneybag” emoji

The TW team thought this had a good chance of getting approved since all that changed was a hand to a stick figure.

Sure, it was more aggressive and eye-catching, but that was the goal. I was fine with the hand/moneybag emoji, which was already approved, so I figured we might as well see if we can go further.

Well, I was wrong.

Day after day, TW wouldn’t give us an official yay/nay and my contacts inside TW told me the new design was causing a lot of heartburn and “big meetings” with folks at the top.

Jack Dorsey was never named, just adam bain, TW COO.

I wasn’t too worried because our plans could continue with the hand/moneybag emoji, even if they denied the more aggressive evolution.

Then, finally, a couple days before the first presidential debate, TW reached out for a call with Dan Greene, VP of US Sales.


  • Newly evolved running stick figure emoji was not approved.
  • Approval on the previously OK’d (hand/moneybag) emoji was pulled back and was no longer allowed to be used.
  • Twitter’s reason: We couldn’t accuse someone of committing a crime they did not commit or were not under investigation for. (Seriously, they said this.)
  • They claimed to fear litigation from HRC.
  • I told them we were trying to show she’s gotten wealthy from public office — they did not budge.
  • I asked, why were able to use (still approved) emojis that showed emails being destroyed or phones being destroyed (which could also represent committing a crime) — they could not explain.
  • I asked, if the Clinton Foundation were being investigated for financial crimes, could we use it — they said no.
  • Dan apologized and admitted TW’s wrongdoing in pulling back an emoji that was previously approved.

To me, this was clearly a BS reason that was made up to give them an out. I was also confidentially told from TW staff that the running stick figure emoji reached Adam Bain, COO, and he personally put a stop to it.

Given that TW had pulled back a previously approved emoji and disrupted our strategy for the debate just days before, we cancelled our promoted trend (costing them hundreds of thousands of dollars).


The next plan was to launch with the second presidential debate. TW, admitting wrongdoing for how they handled the first, extended a $50K discount (“make good”) so we would agree to keep our next trend and give this another shot.

I took them at their word and proceeded. Foolish of me.


  • Worked with TW team and our internal creative team to create a moneybag with wings emoji:
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RNC originally designed emoji on the right and Twitter design, adjusted to meet their specs, on the left
  • Knowing I needed to appease TW’s legal team, I sent it with an explanation to help fend off the HRC lawyers they feared.
  • Explanation: “The emoji represents govt waste and money flying away from taxpayers. Our internal polling has shown this to be a top issue for voters and it’d be inappropriate to restrict us from being able to discuss this important topic.”
  • Wednesday 10/5, we receive approval from their policy and legal team!
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Screenshot from official Twitter PDF with finalized emoji design
  • Thursday, 10/6, we have a call with their comms team to plan the rollout, including the list of media they’ll be leaking the story and emojis to.
  • Slated to launch at 3am ET on Saturday 10/8, with press teasers to go out on Friday 10/7, driven by their comms team.
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Screenshot from a sample tweet sent by TW’s team, showing the emoji in place for launch
  • Friday 10/7 PM, hours before launch, TW asks for a call, with Jack Dorsey, CEO, Adam Bain COO, and Dan Greene, VP US Sales.
  • My internal TW contacts informed me that on Thursday night, 10/6, TW CEO, Jack Dorsey, personally killed the emoji and notified his senior staff.
  • I asked if “There’s going to be another BS legal reason like last time” and they responded, “No, Jack just killed it, there isn’t one.” They were shocked that this was happening.
  • On the call, Jack and Adam started with a lovefest by telling us how great our use of the platform has been. They then told us a last-minute legal review was triggered and they needed to pull the emoji because there wasn’t a paid-for-by disclaimer. (Again. Seriously, they said this.)
  • However, both DNC and RNC conventions had custom emojis this cycle and they did not use disclaimers.
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Red Elephant emoji in use for RNConvention — No disclaimer needed
  • It’s also been reported that a top FEC official has said “the agency does not regulate emojis and that such transparency isn’t required on tweets.”
  • Jack and Adam apologized repeatedly and offered a new incentives package to keep our promoted trend that was just a day away.

We told them it was BS and what they were doing with a public platform was incredibly reckless and dangerous. We voiced that it was clearly a political move and telling us otherwise was just insulting.

Jack maintained their talking points and stayed on message. He also pushed back on it being one-sided, because they were “stopping this feature for ALL political campaigns.”

But, the only other campaign large enough to have this type of deal would have been the Clinton campaign and my contacts inside TW informed me that they did not have one in place.

So basically, “cancelling for all political campaigns” really meant cancelling ONLY for Donald J. Trump’s campaign.

In return, I cancelled our 10/9 and 11/5 promoted trends. Further, I pulled all persuasion and lead gen spending, costing Twitter millions of dollars.

For the past 6 months I’ve been running the digital advertising and fundraising for Donald J. Trump’s presidential campaign.

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