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Welcome back to The Best & The Brightest. I’m Tina Nguyen. Let’s skip past all the obvious (and obviously foretold) results from Super Tuesday, and turn our eye briefly to Congress, where half of the federal budget was just passed. Alas, for the House Freedom Caucus, it was hammered out between Mike Johnson and Chuck Schumer.
 ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ 
The Best & Brightest
Image

Welcome back to The Best & The Brightest. I’m Tina Nguyen.

Let’s skip past all the obvious (and obviously foretold) results from Super Tuesday, and turn our eye briefly toward Congress, where half of the federal budget was just passed. Alas, to the disappointment of the House Freedom Caucus, it was hammered out between Mike Johnson and Chuck Schumer, and increases year-over-year spending without addressing “woke” policies they’d wanted Johnson to eradicate. Thanks to the “laddered” approach, the other seven appropriations bills will come up for a vote next week, which means there’s still time for the rather angry H.F.C. to make their opposition known. Whether they express their anger purely via a protest vote, or a total derailment of the process, remains to be seen. I’ll have the latest on this ladder match tomorrow.

In tonight’s edition, Teddy Schleifer’s exclusive reporting on how Jack Dorsey’s forbidden R.F.K. Jr. flirtation drove a wedge through the Block boardroom—and how Kennedy is leveraging his pull in the crypto community to get his campaign back on track.

But first, Abby Livingston’s chronicle of the Super Tuesday hangover on the Hill…

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Schiff’s Money Magic, More Era-Ending & Sinemania
At last, Super Tuesday gave us a sense of what voters are actually thinking, as opposed to what the political class thinks they are thinking. It also marked the beginning of what will be a vicious congressional primary season. The topline takeaways: It was a good night for Democrats, a good night for right-wing Republicans, and an absolutely dreadful night for the ashes of the traditional Republican establishment. Here’s a little more dish:

  • Schiff-ting to the general: Democrats are elated that Rep. Adam Schiff effectively put the California Senate contest to bed last night after successfully boosting Republican Steve Garvey into the general. (It will be a shock if Garvey, a disco-era baseball star, proves viable in the fall.) What’s so incredible about this campaign is that a single candidate, Schiff, was able to raise enough money to effectively fund two campaigns in the country’s most expensive media markets. Democrats are also pleased that Schiff, and the once-anticipated runner-up, fellow Democrat Katie Porter, will not be competing with their other Senate candidates for donor money.

    Schiff, who raised $33 million cycle-to-date, will presumably arrive in the Senate with an incredible fundraising operation in place. He has major donor bases not just in California, but also Massachusetts, Florida, Texas, and Illinois. Much of that money comes in recurring, small-dollar donations that are nowhere near federal max-out limits. And he has, in part, House Republicans to thank, after their censure vote transformed him into an unlikely political martyr. What he decides to do with those resources—and his willingness to help Democratic colleagues—could make him more than your average Senate freshman.

  • Death of the old order: Super Tuesday was a horrendous night for whatever is left of the pragmatist, pre-Trump Republican establishment. In Texas, Rep. Tony Gonzales is now headed for the political fight of his life in a May runoff, and the situation is even more dire for the state legislature’s moderate-ish Republicans. Granted, Texas is home to a unique version of the G.O.P.’s civil war, but this trend manifested elsewhere, too: Over in Alabama, Freedom Caucuser Barry Moore defeated Jerry Carl in a member-versus-member contest; and North Carolina Republicans chose Mark Robinson, who’s amassed quite the oeuvre of offensive commentary, as their nominee for governor.

    Whether these are harbingers for future primaries remains to be seen: Not all congressional primaries fall on the same date as the presidential contest. Last night, Republicans faced off against Trump voters. Next summer, a whole series of primaries will take place without his specter.

  • A bit more on Sinema’s exit: It’s no secret that Kyrsten Sinema and Arizona’s almost-certain Democratic nominee, Ruben Gallego, have been locked in a long rivalry, dating back to their days as state legislators. But Senate Democratic sources tell me they’re relieved by the grace of her exit—if there are any hard feelings in this contest, they’re barely detectable, with Gallego gearing up to face 2020 election truther Kari Lake.

    Sinema’s colleague Chris Murphy finally said the quiet part out loud (a sentiment that I’ve long heard from Democratic senators): While activists can’t stand her, Sinema was a useful, loyal emissary for Democrats in cutting deals with Republicans. Murphy went so far as to defend her on Twitter last night, writing, “Listen, Kyrsten is way more conservative than me. We disagree on lots. You can think what you want of her, … [But] time after time, big important progressive things have happened bc behind the scenes Krysten wills them to happen. That’s the truth.”

The Rise and Fall of Jack and Bobby
The Rise and Fall of Jack and Bobby
The bizarre and totally unsurprising story of how Jack Dorsey’s advocacy for Robert F. Kennedy Jr. unnerved some members of the Block board.
TEDDY SCHLEIFER TEDDY SCHLEIFER
In the summer of 2023, Jack Dorsey was deathly bored, stupendously rich, and spending way too much time listening to podcasts featuring fringe presidential aspirant Robert F. Kennedy Jr. Dorsey, who had recently opted to keep his $1 billion stake in Elon Musk’s Twitter, was nominally the C.E.O. of Block, his payments company that he had renamed from Square as a way to explore his passion for Bitcoin. But his emerging enthusiasm was presidential politics—in particular, supporting a pro-crypto candidate like R.F.K. At one point, he planned to make a donation to Kennedy’s super PAC on the order of $5 million… in Bitcoin.

Jack’s support for such a controversial figure, after years of disinterest in campaigns, has alarmed people who have worked for him and ostensibly oversee him. “He’s very interested in politics, but he stays an arms length away from it,” said a person who has done political stuff alongside him. Historically, his personal interests have leaned more toward “wellness”—from intermittent fasts to the Myanmar silent meditation retreats to the morning cold plunges. People who know him don’t think he is anti-vax, per se, but Kennedy’s cultivation of the wellness community appeals to him.

Of course, the real political rabbit hole for Dorsey has been cryptocurrency, a cause that has attracted all manner of techno-libertarians and iconoclasts. Kennedy, sensing political opportunity, made an early pitch to the crypto zealots and has continued to make “decentralization” part of his campaign, including during his presentation to the California Libertarian Party convention. Last week, he hosted a fundraiser at a major ETH conference in Denver after delivering the keynote speech. And Jack, who appeared at Bitcoin Atlantis last week in Madeira, sporting a Satoshi T-shirt and a Nostr hat, is all about Bitcoin these days. He believes R.F.K. has legitimized it as a currency, and seems to feel an almost moral imperative to support the candidate.

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Last summer, Jack and Bobby had a private lunch in California, I’m told. Around the same time, Dorsey also had multiple conversations over six weeks with representatives of a pro-Kennedy political action committee called Common Sense. Dorsey wanted to donate about $5 million to the group in Bitcoin to make a point about it being a legitimate currency. Alas, the group discovered that there were tax issues with accepting crypto, and so the idea was curtailed to just some of the money being donated on the blockchain. By early August, the group believed that they were within a day or two of getting the money. Attorneys were in touch. Wire instructions were shared. Stories were already beginning to get placed. And then Jack vanished.

That would have been welcome news at Block. The board of directors, composed of a dozen elder statesmen of finance, technology, and politics, didn’t share Dorsey’s enthusiasm, and his endorsement of R.F.K. even briefly came up at a board meeting that summer. Kennedy, several board members worried privately, was exactly the type of candidate—a raging vaccine-denier who once mused that Covid had been “ethnically targeted” to be less harmful to Jewish and Chinese people—that a public financial services company should have absolutely nothing to do with. And yet, there was Jack, tweeting incessantly about Kennedy, spending hours on podcasts with the likes of vaccine skeptic Russell Brand.

The foundation was laid for considerable boardroom agita, according to multiple sources on both sides. Jack, the controlling shareholder of Block, could essentially do whatever he wanted with the company, and felt he had a right to do so. The board, which includes heavy-hitters like Roelof Botha and Mary Meeker, has famously given Dorsey a long leash for almost 15 years, letting him run two public companies at once and even letting him acquire Tidal, the streaming service run by his friend Jay-Z (with whom he watched the Super Bowl the other week in the same Satoshi shirt). Jack was even able to get Jay on the board.

Soon, however, cracks began to appear in the boardroom. Over the next several months, the two board members with the strongest ties to the Democratic establishment—Larry Summers, the ubiquitous Harvard man and former Treasury secretary, and Darren Walker, the charismatic and just-as-ubiquitous head of the Ford Foundation—resigned before the conclusion of their terms. Their departures were for different reasons and had very different contexts, but it is also true that both were unnerved by what they were seeing that summer in Jack.

The departures of Summers and Walker over the last six months have been much-discussed in Block circles. Summers’ appointment to the board in 2011 was considered big news, at the time, and a sign of the company’s maturity. He was genuinely involved with Block, too—one person described him interviewing candidates for even mid-level jobs. But Summers, a leading critic of antisemitism in American life, was greatly concerned by Jack’s support of Kennedy, according to people he spoke with privately. He even caught some public flak, himself: When Summers was busy working to oust Claudine Gay, his successor at Harvard, for not taking a firm enough stand against antisemitism, the New York Post ran a blurb noting the alleged hypocrisy given Summers’ support for Jack, who in turn supported R.F.K. (Summers left in February—he was no doubt tired from 13 years of service on the board, and his departure came just after he joined the board of OpenAI.)

Walker, for his part, had been one of the more visible board members internally, especially among underrepresented people at the company. A hyper-connected man among the Wall Street elite, he had joined the board in 2020 precisely because he thought banking access for the poor was a worthy cause. Dorsey has alleged to others that Walker stepped down because of his support for R.F.K. There are plenty of reasons why someone might choose to leave a board, but it’s notable that Walker, a member of the powerful audit committee, didn’t even wait for the end of his term to step down after just three years.

Jack in the Box
Jack, seemingly interested in politics for the first time in his life, has spent the last year navigating these hairy dynamics—which, perhaps compared to the bizarre and machination-filled years of Early Twitter (the Ev reign, the Bill Campbell of it all) might seem quaint. And Dorsey may have even learned a few lessons about board management from his youthful days. In the end, he never made any contribution to R.F.K. Instead, Dorsey has told people that he felt he was on thin ice with the board, and had to suppress his political ambitions in the spirit of public company politics and bipartisan bonhomie. (Dorsey didn’t return requests for comments this week. A company spokesperson declined to comment on behalf of the board.)

Of course, the Block board wasn’t the only corpus embarrassed by Dorsey’s political awakening. As I reported last summer, Jack was facing precisely the same pressure from his employees. At an all-hands meeting that June, he was asked by a skeptical employee whether Kennedy was “in line with Block’s mission of economic empowerment” and how Dorsey could “reconcile that against his track record of conspiracy theories.”


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Dorsey responded: “I’m not sure what he’ll do for the country that’s in line with our own mission of economic empowerment,” chewing it over as if he had been asked the question for the first time. “I’ve spent a lot of time listening to all the candidates and on podcasts and what they’ve written and what they’ve shared in a number of Q&As. And the thing I’ve been most impressed with R.F.K. Jr. is how strong he is against regulatory capture and industry’s ability to guide regulators.”

But it was the second part of his answer that raised eyebrows internally. “As it pertains to conspiracy theories, I don’t know,” Dorsey said during the meeting. “I haven’t paid a lot of attention to that part. I’m more concerned with the policies and the ideas and the fight that someone brings to actually change things. And I’m cautiously optimistic, especially relative to all other candidates that we’ve seen, which is kind of a super unfortunate, weak field at the moment.” Ever since then, I’m told, Block employees have been somewhat on edge, checking dutifully every time there are new F.E.C. filings to see whether Jack had finally pulled the trigger on some harebrained donation that they’ll have to defend to their progressive colleagues.

Dorsey seems wary, too. He not only held off on giving money to R.F.K. but also cooled his social media fervor for the candidate on X, where he rarely posts nowadays, and also on Nostr, his decentralized social media platform of choice, where he posts about Kennedy only occasionally. Most importantly, Jack currently isn’t giving interviews—not to Brand, not to Breaking Points host Saagar Enjeti, and not to me—about R.F.K. “He was all about it four months ago. Almost in a manic way. And has totally gone quiet about it in recent times,” said one Block insider who has hoped that Jack would let it go. A donation to Bobby, this person added, has “been an internal worry for a long time.”

Some people close to the company credit the board for having curtailed this activity. But it’s also true that Jack has other things on his mind these days. The Block stock, which skyrocketed during Covid, has fallen dramatically over the past few years, and is now trading at the same level as it was in 2019. Block is also facing potential legal action from multiple government agencies following whistleblower allegations regarding Block’s Cash App. (Regulators are probing whether a lack of due diligence may have left the door open to terrorism funding and money laundering, among other things.) The company recently laid off 10 percent of its workforce, or about 1,000 employees. Jack, a famously hands-off C.E.O., has promised to return to day-to-day management as part of an attempt to right the ship. He also recently lost his brother.

But with his board down to 10 members, Jack also has fewer people to tell him no. And the Kennedy campaign—actively soliciting money from “heterodox” tech billionaires, especially now that it’s clear we’re headed for a Trump vs. Biden rematch—could be persuasive. Dorsey would be an incredible white whale for the R.F.K. operation, especially after the exit of Sheila Creal, the campaign’s finance director. But they also need a strategy to woo other Dorseys. After all, if they can’t get Jack to donate, can they get anyone?

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