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On The Hill

'AN OUTSIDER'S INSIDER': Ayanna Pressley wasn't even in office yet when she was approached by a prominent liberal activist with an unusual idea. 

  • “We urged her to run for DCCC [Democratic Congressional Campaign Committee] chair,” said Adam Green, who approached Pressley at an orientation for freshman lawmakers in November 2018 after discussing the idea with other members of Congress. 
  • “It's unheard of because she was an incoming freshman,” Green, co-founder of the grass roots organization Progressive Change Campaign Committee, told Power Up.

Green said the Massachusetts Democrat, fresh off a stunning upset of 10-term incumbent Michael E. Capuano, was perfectly suited to bridge the gap between the incoming tranche of liberal firebrands and the old guard of the Democratic Party. Pressley, who declined to comment, ultimately did not run. (And it's worth noting that the DCCC, led by Cheri Bustos (D-Ill.) had a massive leadership shakeup yesterday after an uproar over its lack of diversity.) 

Yet these are not exactly the sentiments typically used in Washington to describe members of The Squad.

These four freshman congresswomen of color, who each command armies of followers on social media, are famous for loudly challenging Democratic leadership to move toward the left on everything from impeachment to immigration.

House Speaker Nancy Pelosi has criticized the foursome — which also includes Alexandria Ocasio-Cortez (N.Y.), Ilhan Omar (Minn.), and Rashida Tlaib (Mich.) — for their reactionary style, insisting that compromises are needed to get things done in Congress and a more cautious approach is required to preserve the House majority.

But Green's anecdote captures how Pressley stands out: She is simultaneously a far-left progressive, activist and glass ceiling-shatterer — and a politician who understands Washington and knows her way around the halls of Congress.

  • “Ayanna had great practice for Congress as a staffer,” former Secretary of State John F. Kerry told Power Up. 
  • Pressley worked as a Senate aide to Kerry before she was elected to the Boston City Council where she served for nine years. She then became the first black woman to represent Massachusetts in Congress.
  • "[It] makes Ayanna a better activist on the inside of government that she grew up an activist with Sandra [Pressley, her mother], but then apprenticed on the inside of government as a staffer,” Kerry continued.
  • Key quote: “It makes her a triple threat that she knows how to legislate, advocate, and operate. She's an outsider's insider,” Kerry said.

Pressley has earned praise from people at home for her dual focus on fighting for her constituents and using the national spotlight to President Trump. 

  • “Ayanna actually knows Washington really well,” David McKean, a former U.S. ambassador who was Kerry's Senate chief of staff, told Power Up. “She knows how the Senate works. And so I think from that point of view, she's more experienced and really a veteran. And I think that is much to her credit and/or benefit.” 
  • “Congresswoman Pressley exhibits a type of politician we need — there’s this false assertion that you can’t be idealistic and practical,” Dan Koh, a former chief of staff to Boston Mayor Martin Walsh who worked with Pressley, told Power Up. “And that’s something a lot of the old guard in D.C. are trying to perpetuate.” 

Fault lines: Pressley diverged from other members of the Squad on some of their more controversial positions. Just last week, Pressley voted for a resolution opposing the Boycott, Divestment and Sanctions movement against Israel. AOC, Omar and Tlaib were among just 17 lawmakers who voted against it. 

    And Pressley has maintained a focus on policy prescriptions — even amid the peak of the uproar over Trump's insistence that the Squad “go back” to their ancestral homes. 

    • At a recent news conference the Squad held to address Trump's racist tweets, Pressley notably did not mention impeachment: “This is a disruptive distraction from the issues of care, concern, and consequence to the American people that we were sent here with a decisive mandate from our constituents to work on. Everything from reducing the cost of prescription drugs to addressing our affordable housing crisis, to ensuring that the American people have more than health insurance, but health care.” 

    Of course, Pressley shares many of the same Squad goals: Common positions include abolishing Immigration and Customs Enforcement, and supporting the Green New Deal and Medicare-for-all. 

    • Last week, Pressley filed a bill to abolish the death penalty on the same day that the Department of Justice ordered that capital punishment continue after 16 years without an execution — and AOC, Omar and Tlaib were among its co-sponsors. 

    Pressley's office insisted that the lawmaker is fully committed to Squad unity. Pressley does not “support any attempts to pin her against her freshman colleagues,” a spokesperson told Power Up.

    • More: “In times of hateful and racist rhetoric coming from the president, they are committed to banding together as a united front in resistance to this administration’s cruelty.” 
    The Campaign

    TONIGHT'S DEBATE PREVIEW: If you were hoping for a showdown between Sens. Bernie Sanders (I-Vt.) and Elizabeth Warren (D-Mass.) tonight, think again. The message from their respective camps is that it's not time for the pair (which holds almost one third of the national primary vote) to duke it out.

    • Berning love: “Intelligence,” Sanders said last weekend in Iowa when asked about his expectations for sharing the debate stage with Warren, which CNN’s Gregory Krieg, MJ Lee and Ryan Nobles report.
    • Not exactly fighting words: “That's what Bernie Sanders thinks,” his chief of staff, Ari Rabin-Havt, later told CNN. “He wasn't saying something cute. He was saying something that he truly believes about somebody who he is running against, but who he has immense respect for.” 
    • Warren agrees: “Oh, Bernie and I have been friends forever, since long before I ever got into politics,” she said in New Hampshire, our colleagues Matt Viser and Sean Sullivan report.

    But that doesn’t mean there won’t be fireworks elsewhere. 

    • Bernie is under pressure to go after Biden — a night apart: “[Sanders] is again being advised to draw a sharp contrast with Biden, even though they will not be sharing the same stage,” Sean and Matt write. “One idea was to point to comments in which Biden had assured wealthy donors that ‘nothing would fundamentally change’ for them if he won the presidency.”
    • The moderates might strike back: Former Colorado Gov. John Hickenlooper and former Maryland Rep. John Delaney have both made names for themselves questioning Sanders and Warren’s leftward push on the party.
    • Beto needs a big moment: “After a first debate appearance that raised alarm among [the former Texas congressman's] major donors, there is ever-increasing pressure on O’Rourke to shine at Tuesday’s debate and remind Democrats why so many thought he could be a front-runner just a few months ago, our colleague Jenna Johnson writes
    • How the campaigns are preparing: “One of the things that we learned is that it is a total free-for-all. It was like a children’s soccer game, 10 candidates swarming the ball,” a senior adviser to one of the candidates told Matt and Sean. “We have done a lot less practice of what your 60-second answer is and a lot more practice of live-fire drills of how to interject into the debate.”
    • A reminder of the new rules: No one-word or hand-raising questions. A promise to cut time for those who, ahem, interrupt too often. Here is a rundown of the rest, per our colleague Amber Phillips. 

    Fighting for a spot: The next two nights are critical for a large number of candidates. If they don't have a big moment, you may not see them on the debate stage again. The rules for making the stage get increasingly harder in September. Candidates, who once qualified just by the amount of donors and poll numbers, will soon need to have both. 

    Right now, according to Politico's tracker, there are only seven candidates who meet both the new polling and donor thresholds. 

    • That means the ones to watch this week are really: Former Housing and Urban Development Secretary Julián Castro and businessman Andrew Yang, who have met the donor threshold but not the polling threshold. And Sen. Amy Klobuchar (Minn.) has hit only the polling mark.
    • And the 10 candidates you'll see on stage this week, who have not yet met either threshold: They are: Hickenlooper and Delaney, Sens. Michael Bennet (Colo.) and Kirsten Gillibrand (N.Y.); Reps. Tulsi Gabbard (Hawaii) and Tim Ryan (Ohio); Montana Gov. Steve Bullock; Washington Gov. Jay Inslee; New York Mayor Bill de Blasio; and author Marianne Williamson. (And businessman Tom Steyer, who announced his run too late for this debate.)
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    In the Media



    MAKING MONEY MOVES: "Sen. Bernie Sanders on Monday teamed up with rapper Cardi B to film a 2020 presidential campaign video meant to appeal to young voters," CNN's  Annie Grayer reports.