Playbook Deep Dive POLITICO

Cuba’s sweeping protests — and sweeping crackdown — are historic. But the situation is a political hot potato for Biden, whose sanction orders came nearly two weeks after the unrest began. His go-it-slow approach has emboldened Republicans, while Florida Democrats fear the president could blow an opportunity to reorient U.S.-Cuba policy and improve the party’s political chances in a former swing state. POLITICO’s Sabrina Rodríguez and Marc Caputo unpack the political minefield with Playbook's Tara Palmeri.

$1.6 trillion — that's how much student loan debt there is in the United States. Progressives want to cancel student loan debt. Republicans say that's wildly unfair. And President Joe Biden is....waiting. Playbook co-author Tara Palmeri and education reporter Michael Stratford discuss the fight on Capitol Hill over student loans and whether Biden could tackle the problem through executive action.

Michigan’s Oakland County, once a Republican stronghold, is turning blue. Playbook's Eugene Daniels and Zack Stanton (also a Michigan native — he's from the "knuckle"), talk about whether shedding these suburbs is a warning light for Trumpism. Plus: Former Michigan GOP leader Jeff Timmer on what he thinks losing this stronghold says about the strength of a Republican electoral map.

Eight — that’s how many states have passed some form of cannabis legalization since November. And even though marijuana is gaining popularity in conservative states, that's not breaking through with GOP senators on Capitol Hill. Cannabis reporter Natalie Fertig and Playbook co-author Tara Palmeri discuss the growing cannabis dissonance between Republican senators and voters in their home states, and why Chuck Schumer shouldn’t be optimistic about passing federal legislation.

Matthew Caulfield was a college senior when he was given a seemingly simple assignment that took him more than five years and 3,000 emails to start to answer: How much did a voting machine cost? And how big, precisely, was the U.S. elections industry? Playbook co-author Eugene Daniels and reporter Ben Wofford dive into the mysterious world of voting technology companies and the voting rights debate happening right now in Congress.

It’s one of the top jobs in politics, period: mayor of the Big Apple. In a heavily left-leaning town, Tuesday’s crowded Democratic primary will essentially decide who will become the 110th mayor of New York City — an election that will determine who has the ear of powerful figures on Capitol Hill. POLITICO New York’s Sally Goldenberg and Playbook co-author Tara Palmeri unpack the race while producer Olivia Reingold pounds the pavement to find out what New Yorkers really think.