FDR vs. The Supreme Court, 1937
Franklin D. Roosevelt wielded the power of the executive more forcefully than any president before him, so it's unsurprising that he should make this list. (In fact, he almost made the list more than once.) In arguably his most infamous power push, in 1937 FDR decided the Supreme Court couldn't handle its caseload and proposed upping the number of justices on the bench. Or, at least that was what he often told the public. But the real reason President Roosevelt wanted to expand the court was because it had struck down much of his expansive New Deal legislation and he hoped more judges, which he would appoint himself, would turn the tides in his favor. Ultimately, his proposed Judicial Procedures Reform Bill failed though, in large part because he failed to win over the American public, who viewed the court-packing proposal as an unprecedented overreach into the judicial branch.