Welcome back to The Best & The Brightest.

Teddy Schleifer here, at the helm this Tuesday with three scoops from the intersection of politics and philanthropy: Jack Dorsey’s awkward defense of his R.F.K. Jr. support; the bonkers fundraising schedule in the Bay Area over the next week, featuring a visit from self-funding billionaire Doug Burgum; and some news on a high-profile political departure from the orbit of Wall Street legend Dan Loeb.

But before all that, a quick update on Biden’s last-minute West Coast fundraising trip, followed by Abby Livingston’s already-essential daily report from the Capitol Hill cafeteria.

But first…

• Mark Your Calendars!: After much delay, the somewhat last-minute Joe Biden West Coast fundraising trip I previewed several weeks ago is officially papered and happening, according to three invites I’ve seen. Biden has two events in the South Bay on June 19, Juneteenth—a Los Gatos reception co-hosted by Reid Hoffman and at the home of top fundraiser Shannon Hunt-Scott and her husband Kevin, the C.T.O. of Microsoft; and a second at the home of Steve Westly and Anita Yu in Atherton.

  Both of those events have a $25,000 minimum for attendance. There’s a cheaper event the following day at the Marin County home of Stephanie Robinson with “special guest” Gavin Newsom (minimum: $5,000). Interestingly, Biden will actually be in the Bay Area at the same time as Ron DeSantis, who has an event on the 19th hosted by Embarcadero Capital Partners’s John Hamilton, in Woodside, just a few miles away from where Biden will be that day.

By Abby Livingston

• McCarthy’s Case of the Mondays: It’s not normal for a speaker to cancel a House vote, but it’s really not normal to cancel votes on a Monday night, as Kevin McCarthy did yesterday evening with mere minutes’ notice. At least one Congressional office had all of a three-minute heads-up, at 6:27 p.m., just ahead of a 6:30 vote.

  Canceled votes usually signal trouble—in this case, fallout from a standoff between McCarthy and about 11 rebellious Republicans exacting retribution over the debt ceiling deal he cut with Democrats. But the fact that it all went down on a Monday night raised more than a few eyebrows since House members flew in from all over the country to be present for a vote that never happened.

  What’s even more abnormal are reports of an astonishing House G.O.P. meeting Tuesday morning, that devolved into screaming and swearing. A source close to leadership confirmed to me that tensions are high and the vast majority of House Republicans are running out of patience with McCarthy’s concessions to the comparatively small handful of Republican rebels.

• What Will Jamie Do?: One of the biggest questions on Democratic minds these days is whether Jamie Raskin, the popular Maryland congressman and Trump impeachment star, will enter the open-seat race to replace Senator Ben Cardin. Raskin is ambitious, of course, and the Senate is typically considered a promotion (and possibly a stepping-stone to even higher office). Nevertheless, Raskin would leave much behind in the House. Late last year, he secured the top Democratic post on the House Oversight Committee, the most politically charged House investigative arm. And he did it with astonishing speed.

  Democrats take seniority incredibly seriously, and for good reason: It typically takes decades of patience to become a chair or ranking member, and yet Raskin accomplished the feat in just six years, leapfrogging several more senior members. But Oversight chair is not a fun job while in the minority, especially with a president from the same party in office. As such, much of Raskin’s job this term is playing defense on G.O.P. investigations into the Biden administration and into the business practices of the president’s son, Hunter.

  If Raskin stays put, the chairman role would offer him sprawling powers to investigate and to subpoena witnesses once Democrats are back in the majority. The Democratic primary is nearly certain to determine the winner, but Raskin would face a competitive nomination fight. After all, the Senate Democratic primary field includes a former political rival and self-funding colleague, David Trone, and Prince George’s County Executive Angela Alsobrooks, who has the backing of Steny Hoyer. This is likely a safe Democratic seat. The fourth-term congressman told CNN’s Dana Bash earlier this month he hopes to make a decision before the Fourth of July.

• D.C.’s Field of Dreams: Congress members, staffers and lobbyists will decamp to Nationals Park Wednesday night for the annual Congressional Baseball Game, which pits bicameral rosters of Republicans against Democrats. It’s the biggest night of the year in Congressional circles—mainly because it’s the one event all year that everyone is invited to attend.

  Republicans hope to extend a two-year winning streak. Previously, Democrats went on a near-perfect ten-year tear, a period that coincided with the congressional career of Cedric Richmond, a Democrat from New Orleans. A Morehouse College baseball phenom, Richmond was possibly the most dominant member to ever play the game.

  Nobody was happier than Hill Republicans, in 2020, when Joe Biden named Richmond a senior adviser in late 2020. The G.O.P. has since won both games, and last year’s game ended in a 10-0 shutout.

Dorsey’s answer to the pre-submitted question began predictably enough. “I’m not sure what he’ll do for the country that’s in line with our own mission of economic empowerment,” said Dorsey, wearing a plain black t-shirt and his signature beard. “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.”

He continued: “So as it pertains to our own industry, we’re certainly in an industry that has a lot of influence by very, very large financial entities that have a tendency to potentially steer regulators in particular ways and are not necessarily leveling the playing field for individuals. That’s why we started the company, literally.”

But it was the second part of his answer that raised eyebrows internally, I’m told. “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.”

Not entirely surprising, perhaps, for a new-age wellness-obsessed C.E.O. who famously took weeks off work from Twitter and Block to go on silent vipassana meditation retreats. And, of course, Dorsey is hardly a heavy hitter in the political arena—he cares a lot about social-justice issues, but he is not considered a deep thinker on public policy. Still, it scarcely passes the smell test for Jack to suggest that he “hasn’t paid a lot of attention” to Kennedy’s position on vaccines, especially if he has been spending “a lot of time” listening to what R.F.K. has been saying publicly. He wasn’t asked about R.F.K.’s anti-vax platform in a rare interview he did this week with Saagar Enjeti and Krystal Ball, just saying that it was “refreshing” to have a candidate who “has no fear in exploring topics that are a little bit controversial.” True!

The sixth presidential fundraiser in the area, until now under wraps, is the most intriguing. While Doug Burgum, the business-friendly Republican governor of North Dakota, has been planning to largely self-finance his quixotic ’24 bid, I’ve learned that he’s actually going to raise some outside money—a fact confirmed by a Burgum campaign aide. I am told he’ll be in the Bay Area at an event hosted by Dick Boyce, a veteran G.O.P. fundraiser and a former TPG executive, and Hamid Moghadam, the C.E.O. of Prologis and an increasingly active player in local and national politics.

Burgum, obviously, is a longshot among longshots, but he probably has the strongest real relationships with the tech industry of any of the dozen Republicans running for the presidency. In the ’80s and ’90s, Burgum built an accounting software company, Great Plains Software, which he sold to Microsoft for a cool $1 billion. He went on to work for Bill Gates and Steve Ballmer there, overseeing the company’s enterprise business. He’d later become a V.C. focused on the Midwest—he had a small-potatoes firm based in Fargo—but continued to serve as the chairman of SuccessFactors and then Atlassian, the Australian software juggernaut, both of which had billion-dollar-plus exits.

That’s all to say that Burgum is actually credible with some elites, and I wouldn’t be shocked to see some of them—like Ballmer, perhaps, who is still a Burgum friend—get involved with his campaign or back it. Voters, obviously, are a different story.

While not a household name, Cook-McCormac has been a well-known figure in national political circles since helping Loeb and other like-minded donors pass New York’s gay-marriage bill in 2011. (Cook-McCormac was one of the architects of a strategy to organize donors and create the political conditions such that it was easier for Republicans to vote for gay marriage than to oppose it.) He then went to work in-house for Loeb, joining his hedge fund, Third Point, as the firm’s Head of Public Affairs in 2015. He effectively served as Loeb’s lobbyist, pushing his priorities like charter schools and criminal-justice reform, as well as advocating for the usual hedge fund-specific issues.

But Cook-McCormac recently stepped down from Third Point, I’ve learned. He is striking out on his own with a lobbying shop called Ius Impact, where his first lobbying-registration clients include a bunch of Loeb priorities, such as Success Academy Charters and the Council for Investor Rights and Corporate Accountability.

Some people in my ear have been buzzing about his departure and what it portends for Loeb’s engagement in politics going forward: Third Point has had a poor run as of late… without Cook-McCormac, and perhaps less money, could Loeb be preparing to back away a bit from his political bets? I’m told that the answer is, more or less, no, the exit was amicable, that Dan and Jeff remain close, and that Loeb is going to stay active in politics with philanthropy chief Daniel Sperling—just without his full-time eyes and ears for the last few years. I’ll be watching to see who Loeb backs in ’24. I’ve heard one of his big bets could be Chris Christie, who I know many major donors want to see on a G.O.P. debate stage.