Headline: Tracking Trump's Legal Battles: A High-Stakes Supreme Court Showdown in 2026

I never thought I'd be glued to my screen tracking court battles like they're the Super Bowl, but here we are in mid-January 2026, and President Donald Trump's legal showdowns are dominating the dockets from Hawaii to the Supreme Court steps in Washington, D.C. Just this past week, as the Supreme Court wrapped up arguments in cases like Chevron USA Inc. v. Plaquemines Parish in Louisiana and Little v. Hecox, all eyes shifted to Trump's escalating clashes with federal agencies and old foes. On Friday, January 16, SCOTUSblog reported the justices huddled in private conference, voting on petitions that could add more Trump-related fireworks to their calendar.

Take Trump v. Cook, heating up big time. President Trump tried firing Lisa Cook, a Democratic holdover on the Federal Reserve Board of Governors, back in August 2025, calling her policies a mismatch for his America First agenda. U.S. District Judge Cobb in Washington blocked it, and the D.C. Circuit Court of Appeals upheld her ruling 2-1. Now, the Trump administration, led by Solicitor General D. John Sauer, is begging the Supreme Court to intervene. Oral arguments hit Wednesday, January 21, at 10 a.m. in the Supreme Court building, with Paul Clement—former Solicitor General under George W. Bush—defending Cook. Sauer blasted the lower courts as meddling in presidential removal power, echoing fights in Trump v. Slaughter, where the Court already chewed over firing FTC Chair Lina Khan's allies like Alvaro Bedoya last December. Dykema's Last Month at the Supreme Court newsletter calls it a direct shot at the 1935 Humphrey’s Executor precedent, questioning if Congress can shield multi-member agency heads from the president's axe.

It's not just agency drama. E. Jean Carroll, the former Elle writer who won $5 million defaming her after a jury found Trump liable for sexually abusing her in a Bergdorf Goodman dressing room in the 1990s, just urged the Supreme Court to swat down his latest petition. ABC News covered her filing this week, where she argues U.S. District Judge Lewis Kaplan in New York got evidence rules spot-on—no reversal needed.

And that's barely scratching the surface. The Court’s January calendar, straight from supremecourt.gov, lists Trump v. Cook smack in the middle, following Wolford v. Lopez on Tuesday, January 20—a Second Amendment tussle over Hawaii's law banning guns on private property open to the public without the owner's okay. Axios predicts 2026 bombshells like Trump v. Barbara on his executive order gutting birthright citizenship under the 14th Amendment, potentially stripping citizenship from kids of undocumented immigrants born on U.S. soil. Then there's Learning Resources v. Trump, challenging his national emergency tariffs on foreign goods—Axios says a loss could force $100 billion in refunds and crimp his trade wars.

Over in lower courts, Just Security's litigation tracker logs fresh salvos: challenges to Executive Order 14164 jamming January 6 convicts into ADX Florence supermax in Colorado, and suits against orders targeting law firms like Perkins Coie, Jenner & Block, and WilmerHale for alleged anti-Trump bias. Lawfare's tracker flags national security spins on these executive actions. Even California Republicans appealed a Los Angeles panel's smackdown of their gerrymander claims against Governor Gavin Newsom's maps to the Supreme Court this week, per SCOTUStoday.

These cases aren't just legal jargon—they're power plays reshaping the presidency, from Fed independence to gun rights and citizenship. As Trump posts fire on Truth Social about "evil, American-hating forces," the justices gear up for a term that could torch decades of precedent.

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