Good Morning, and Happy Saturday! Welcome to The Flag's Five, your nonpartisan breakdown of the week’s five most pressing headlines. Dive into what happened, why it matters, and how perspectives from the left and right shape the conversation.

Want more? Upgrade today to unlock The Flag's Sunday Edition, where we uncover fascinating American historical stories—and enjoy an ad-free reading experience while you're at it. History, clarity, and no interruptions await!

1. Deported Dad Sent to Notorious El Salvador Prison

• Here's what happened: Kilmer Armando Abrego-Garcia, a Maryland father who was granted asylum in 2019, was mistakenly deported to El Salvador by ICE due to what the agency called an “administrative error.” Despite having protected legal status in the U.S., he was transferred to a high-security prison in El Salvador, which houses members of violent gangs like MS-13. A lawsuit filed by his attorneys argues that Abrego-Garcia has no ties to any criminal organizations and is being unlawfully detained. Since he is no longer in U.S. custody, a federal court cannot compel his return. (Kevin Bohn, News Nation)

• Here's why it matters: The deportation of Abrego-Garcia has sparked outrage among immigrant rights advocates and his Maryland community, who fear for his safety. The incident raises broader concerns about due process failures and the vulnerability of protected immigrants caught in the crosshairs of immigration enforcement. Critics say this case could set a dangerous precedent if not remedied. (Polo Sandoval and Priscilla Alvarez, CNN)

• Here's what right-leaning sources are saying: Some conservative commentators argue that Abrego-Garcia should not have been in the U.S. to begin with, citing discrepancies in his immigration status. The Washington Examiner emphasizes that he was only granted asylum after a prior claim of gang affiliation in 2019, framing his deportation as legally valid despite the later reversal. (Conn Carroll, Washington Examiner)

• Here's what left-leaning sources are saying: Progressive outlets are highlighting this case as a major human rights failure, with The Daily Beast calling it a “massive mistake” that has left a father unjustly imprisoned. The report criticizes the government’s refusal to facilitate his return, despite acknowledging the deportation was in error. (Jana Brancolini, The Daily Beast)

Sponsored by Masterworks

Over the last seven elections, this asset class has outpaced the S&P 500

Instead of trying to predict which party will win, and where to invest afterwards, why not invest in an ‘election-proof’ alternative asset? The sector is currently in a softer cycle, but over the last seven elections (1995-2023) blue-chip contemporary art has outpaced the S&P 500 by 64% even despite the recent dip, regardless of the victors, and we have conviction it will rebound to these levels long-term.

Now, thanks to Masterworks’ art investing platform, you can easily diversify into this asset class without needing millions or art expertise, alongside 65,000+ other art investors. From their 23 exits so far, Masterworks investors have realized representative annualized net returns like +17.6%, +17.8%, and +21.5% (among assets held longer than one year), even despite a recent dip in the art market.*

It's easy to get started at Masterworks, and our readers can SKIP THE WAITLIST HERE.

2. Booker Sets Senate Speech Record at 25 Hours

• Here's what happened: Senator Cory Booker delivered a 25-hour speech on the Senate floor this week, surpassing Strom Thurmond’s 1957 record. Though not technically a filibuster, Booker’s marathon speech was a pointed critique of Trump-era spending cuts and executive overreach. He invoked civil rights history in his remarks, declaring, “It should not be possible in America for one single man — even an elected president — to stop funds which Congress has already allocated.” (Juana Summers et al., NPR)

• Here's why it matters: Booker’s speech drew national attention not just for its duration but for its symbolic defiance. While it did not block legislation, it sparked debate about presidential power, budget priorities, and congressional authority. The speech was also a physical feat—Booker spoke continuously without bathroom breaks or food, relying on hydration techniques and Senate procedural loopholes. (Filip Timotija, The Hill)

• Here's what right-leaning sources are saying: Conservative outlets largely mocked Booker’s speech, characterizing it as a performative rant. The Gateway Pundit referred to him as “bug-eyed” and accused him of using the Senate floor to vent about Trump and Elon Musk without offering concrete legislative action. (Cristina Laila, The Gateway Pundit)

• Here's what left-leaning sources are saying: Progressive platforms praised Booker’s speech as a bold stand that reignited Democratic momentum. Axios called it “epic” and noted how it shifted national attention back to Democratic priorities and leadership, especially as the party tries to rally ahead of the 2026 midterms. (Sareen Habeshian, Axios)

3. Mixed Results in Key State Elections

• Here's what happened: On Tuesday night, voters in Wisconsin and Florida cast ballots in three notable races. In Wisconsin, liberal Justice Susan Crawford won a seat on the state’s Supreme Court, ensuring a liberal majority. Meanwhile, Republicans secured victories in two special elections for Florida’s House seats. Crawford’s win comes in a state that was pivotal in the 2020 presidential election and is expected to be closely contested again in 2024. (Martha McHardy, Newsweek)

• Here's why it matters: The results signal a complex political landscape heading into the 2026 midterms. Democrats celebrated the Wisconsin win as a judicial safeguard for voting rights and redistricting challenges. Republicans, on the other hand, emphasized their resilience in Florida, reinforcing the state’s GOP dominance. The outcomes also highlight voter engagement in off-year elections and suggest both parties are refining their strategies ahead of national contests. (Domenico Montanaro, NPR)

• Here's what right-leaning sources are saying: Conservative analysts focused on the Florida wins as evidence of Republican strength in a critical battleground state. The Washington Examiner also framed the Wisconsin result as a potential motivator for conservative voters, arguing that Democrats are “pushing the envelope” through court victories, which could rally GOP turnout in 2026. (Byron York, Washington Examiner)

• Here's what left-leaning sources are saying: Progressive voices emphasized the warning signs for Republicans. The Guardian pointed to Crawford’s victory as a bellwether that voters are increasingly rejecting MAGA-aligned candidates and legal strategies. The article argued the results should concern Trump’s inner circle, particularly given the Wisconsin court’s potential role in future election disputes. (Lloyd Green, The Guardian)

4. Trump Unveils Broad New Tariffs Amid Backlash

• Here's what happened: On Wednesday, former President Donald Trump announced sweeping new trade tariffs, including a 10% universal tariff on all imports and reciprocal tariffs targeting 60 specific countries. Trump framed the move as a strategic reset to protect American industry, declaring, “The operation is over!” Financial markets responded with volatility following the announcement. (Ryan King, New York Post)

• Here's why it matters: The tariffs could drive up prices on a wide range of everyday goods, from smartphones and appliances to food and clothing. Economists warn this approach risks reigniting inflation and placing a strain on American consumers. With more than 60 countries affected, the new tariffs may also trigger retaliatory trade actions and disrupt global supply chains. (Annie Nova andGreg Iacurci, CNBC)

• Here's what right-leaning sources are saying: While some conservatives support Trump's protectionist approach, major right-leaning outlets like National Review sharply criticized the move. The editorial board called the tariffs “reckless,” warning they would function as a tax hike on American families and businesses. They argue the policy reflects short-term political strategy over sound economic principles. (The Editors, National Review)

• Here's what left-leaning sources are saying: Progressive sources were similarly critical, with MSNBC calling the tariffs “incoherent and destructive.” The piece described the move as economically self-sabotaging and ideologically muddled, asserting that it risks economic pain without delivering meaningful gains in manufacturing or job growth. (Jessica Riedl, MSNBC)

Sponsored by Masterworks

Over the last seven elections, this asset class has outpaced the S&P 500

Instead of trying to predict which party will win, and where to invest afterwards, why not invest in an ‘election-proof’ alternative asset? The sector is currently in a softer cycle, but over the last seven elections (1995-2023) blue-chip contemporary art has outpaced the S&P 500 by 64% even despite the recent dip, regardless of the victors, and we have conviction it will rebound to these levels long-term.

Now, thanks to Masterworks’ art investing platform, you can easily diversify into this asset class without needing millions or art expertise, alongside 65,000+ other art investors. From their 23 exits so far, Masterworks investors have realized representative annualized net returns like +17.6%, +17.8%, and +21.5% (among assets held longer than one year), even despite a recent dip in the art market.*

It's easy to get started at Masterworks, and our readers can SKIP THE WAITLIST HERE.

The content is not intended to provide legal, tax, or investment advice. No money is being solicited or will be accepted until the offering statement for a particular offering has been qualified by the SEC. Offers may be revoked at any time. Contacting Masterworks involves no commitment or obligation. 

“Net Annualized Return” refers to the annualized internal rate of return net of all fees and expenses, calculated from the offering closing date to the date the sale is consummated. IRR may not be indicative of Masterworks paintings not yet sold and past performance is not indicative of future results. For additional information regarding the calculation of IRR for a particular investment in an artwork that has been sold, a reconciliation will be filed as an exhibit to Form 1-U and will be available on the SEC’s website. Masterworks has realized illustrative annualized net returns of 17.6% (1067 days held), 17.8% (672 days held), and 21.5% (638 days held) on 13 works held longer than one year (not inclusive of works held less than one year and unsold works).

Contemporary art data based on repeat-sales index of historical Post-War & Contemporary Art market prices from 1995 to 2023, developed by Masterworks. There are significant limitations to comparative asset class data. Indices are unmanaged and a Masterworks investor cannot invest directly in an index.

5. Eric Adams to Run for Reelection as Independent

• Here's what happened: New York City Mayor Eric Adams announced he will seek reelection as an independent, bypassing the Democratic primary. While remaining a registered Democrat, Adams said he will launch a new party focused on centrist values and public safety. The move follows a federal judge’s dismissal of bribery and campaign finance charges against him earlier this week—charges Adams claims would have undermined his standing in a primary contest. (Anthony Izaguirre, Associated Press)

• Here's why it matters: Adams’ decision adds a twist to what could now become a volatile and unpredictable mayoral race in one of the nation’s most influential cities. His ongoing tension with the Democratic establishment, coupled with legal drama, sets the stage for a possible three-way race. Analysts say the decision reflects both political calculation and a bid to recast himself as an outsider candidate with crossover appeal. (Sally Goldenberg, Politico)

• Here's what right-leaning sources are saying: Conservative outlets see Adams’ move as a sign of fracturing within the Democratic Party. The New York Post editorial board suggested his independent run could shake up the city's political status quo and create unexpected opportunities for challengers, calling it the beginning of a “wild election year.” (Post Editorial Board, New York Post)

• Here's what left-leaning sources are saying: Progressive voices focused more on the legal aspect, with MSNBC celebrating the dismissal of charges as a win for judicial integrity. They highlighted Judge Dale Ho’s rebuke of Trump-era DOJ interference and the vindication of prosecutors who resisted political pressure. (Mimi Rocah, MSNBC)

Sunday Sneak Peak

🐻 Bought for pennies an acre, mocked as an icy mistake—Alaska turned out to be anything but. What made this purchase pure geopolitical gold? Discover the deal of the century in The Flag! Subscribe today.