He sided with Jehovah's Witnesses seeking to invoke the First Amendment in cases such as West Virginia State Board of Education v. Barnette (1943) and Murdock v. Pennsylvania (1943); his majority opinion in Thomas v. Collins (1945) endorsed a broad interpretation of the Free Speech Clause.

[9]: 111 [10]: 375  Rutledge frequently weighed in on questions of public importance, supporting academic freedom and free speech at Washington University and opposing the Supreme Court's approach to child labor laws.

[6]: 331 [10]: 375  In Rutledge's view, the justices of his era had "imposed their own political philosophy" rather than the law in their decisions; as such, he felt that expanding the Court was a regrettable but necessary way for Congress to bring it back into line.

[1]: 125–127  Roosevelt's proposal was extremely unpopular in the Midwest, and Rutledge's support for it was loudly denounced: his position even led some members of the Iowa legislature to threaten to freeze faculty salaries.

[9]: 112  In Busey v. District of Columbia,[a] for instance, he dissented when the majority upheld several Jehovah's Witnesses' convictions for distributing religious literature without securing a license and paying a tax.

[12]: 94  His opinion for the court in Wood v. United States[b] reversed a conviction for robbery that had been secured after the defendant pleaded guilty at a preliminary hearing without having been informed of his right against self-incrimination.

[2]: 1317  Rutledge wrote that the preliminary hearing was not supposed to be "a trap for luring the unwary into confession or admission which is fatal or prejudicial"; he held that a plea was not voluntary if the defendant was not aware of his constitutional rights.

[15]: 186  According to the scholar Fred L. Israel, Roosevelt found Rutledge to be "a liberal New Dealer who combined the President's respect for the academic community with four years of service on a leading federal appellate court".

[16] Those four senators—North Dakota's William Langer, West Virginia's Chapman Revercomb, Montana's Burton K. Wheeler, and Michigan's Homer S. Ferguson—abstained due to uneasiness about Rutledge's support for Roosevelt's court-expansion plan.

[1]: 260–261  For instance, in Jones v. City of Opelika,[c] a 1942 case decided before Rutledge's ascension to the Court, a 5–4 majority had upheld the convictions of Jehovah's Witnesses for selling religious literature without obtaining a license and paying a tax.

[21]: 419–421  Writing for a 6–3 majority that included Rutledge, Justice Jackson wrote that: "[i]f there is any fixed star in our constitutional constellation, it is that no official, high or petty, can prescribe what shall be orthodox in politics, nationalism, religion, or other matters of opinion or force citizens to confess by word or act their faith therein".

[22]: 218  The case arose when R. J. Thomas, an official of the Congress of Industrial Organizations, gave a pro-union address in Texas without having registered; he argued that the law was an unconstitutional prior restraint on his First Amendment rights.

[9]: 181  Rutledge rejected Texas's arguments that the law was subject only to rational-basis review because labor organizing was akin to the sort of ordinary business activity that states could freely regulate.

[1]: 269  Writing that "the indispensable democratic freedoms secured by the First Amendment" had a "preferred place" that could be abridged only in light of a "clear and present danger", he held that the law imposed an unjustified burden on Thomas's constitutional rights.

[9]: 266–267  But despite what Wiecek called a "fusillade of sweeping dicta", Black nonetheless held for a 5–4 majority that the specific law at issue—a New Jersey statute that permitted parents to be reimbursed for the costs of sending their children to private religious schools by bus—did not violate the Establishment Clause.

[9]: 262, 267  In dissent, Rutledge favored an even stricter understanding of the Establishment Clause than Black, maintaining that its purpose "was to create a complete and permanent separation of the spheres of religious activity and civil authority by comprehensively forbidding every form of public aid or support for religion".

[1]: 268 In other cases, Rutledge evinced a near-uniform tendency to embrace defenses rooted in the First Amendment: in Terminiello v. City of Chicago,[i] he sided with a priest whose rhetorical attacks on Jews and the Roosevelt administration had provoked a riot; in United Public Workers v. Mitchell[j] and Oklahoma v. United States Civil Service Commission,[k] he dissented when the Court upheld the Hatch Act's restrictions on civil servants' political activity; in Marsh v. Alabama,[l] he joined the majority in holding a company town's restrictions on the distribution of religious literature unconstitutional.

[24]: 40  Concurring separately, he argued for a broader definition of due process, decrying the Court's willingness to permit "selective departure[s]" from the "scheme of ordered personal liberty established by the Bill of Rights" in other cases.

[1]: 373  Aided by his law clerk John Paul Stevens,[25]: 507  Rutledge dissented, concluding that the court in the District of Columbia had jurisdiction because the person having custody over the prisoners—the Attorney General—was located there.

[28]: 155  Since the United States had not yet signed a peace treaty with Japan, he maintained that the Articles of War permitted military trials to be conducted without complying with the Constitution's due process requirements.

[9]: 330  The two dissenters—Murphy and Rutledge—each filed separate opinions; according to Yamashita's lawyer, they read them "in tones so bitter and in language so sharp that it was readily apparent to all listeners that even more acrimonious expression must have marked the debate behind the scenes".

[30]: 45  In his dissent, he rejected the majority's holding that the Fifth Amendment was inapplicable, writing that: "[n]ot heretofore has it been held that any human being is beyond its universally protecting spread in the guaranty of a fair trial in the most fundamental sense.

The Court has not been involved with any war crimes trials in several decades, but aside from the jurisdictional issue it is clear that the ideas expressed by Wiley Rutledge—in terms of both due process and command accountability—have triumphed.

[1]: 242  The Court unanimously rejected his plea: in an opinion by Chief Justice Stone, it refused to question the military's assertion that the relocation program was critical to national security.

[7]: 132–133  Green also argues that the modern condemnation of the Court's decision benefits substantially from hindsight: after the attack on Pearl Harbor, the threat of sabotage appeared serious, and the government had hidden information that would have raised doubts about the accuracy of its assessments.

[34]: 127–128  Writing that the Equal Protection Clause "require[s] lawmakers to refrain from invidious distinctions of the sort drawn by the statute challenged in this case", Rutledge maintained that Michigan's law was arbitrary and irrational.

[33]: 445  In Colegrove v. Green,[aa] voters challenged an Illinois congressional apportionment scheme that created districts with unequal numbers of people, arguing that it violated federal law and the Constitution.

[22]: 642  Again parting ways with Black, Douglas, and Murphy but refusing to join the majority's analysis, Rutledge declined to grant the Progressive Party relief, maintaining that there was not enough time before the election for the state to print new ballots.

[2]: 1321  Rutledge's dissent was rendered in the midst of substantial hostility among political leaders and the general public toward the union's actions, and the scholar Fred L. Israel characterized it as "courageous".

[44]: 413  Timothy L. Hall argued in 2001 that Rutledge's judicial career "was like the unfinished first symphony of a composer who might have gone on to create great masterpieces but who died before they could ever flow from his pen ... [H]is steady outpouring of opinions over the course of six years yielded only a tantalizing glimpse of what might have been.