Architect of original Sisyphean task / THU 2-25-21 / Collaborator on 1968's Two Virgins familiarly / Garment whose name comes from Malay for sheath / Surname of two former Chicago mayors / Vintage diner fixture in brief / Psyche's mate in Greek mythology

Constructor: Dylan Schiff

Relative difficulty: Easy-Medium

THEME: DOUBLE DOWN (32D: Blackjack bet ... or a hint to applying the five circled regions in this puzzle) — wow, "applying" is a weird word here; you just "Double" the circled squares in the long "Down" answers to get your actual answers:

Theme answers:

• HANGING INDENT (3D: Feature of some bibliographic citations)
• COVER VERSION (36D: Whitney Houston's "I Will Always Love You," for example)
• HEART MURMUR (6D: Stethoscope detection)
• BARBARA BUSH (41D: Former first and second lady)
• STEAK TARTARE (10D: Dish often topped with raw egg yolk)

Word of the Day: Bill AYERS (22A: Bill ___, noted Vietnam War-era activist) —

William Charles Ayers (/ɛərz/; born December 26, 1944) is an American elementary education theorist. During the 1960s, Ayers was a leader of the Weather Underground that opposed US involvement in the Vietnam War. He is known for his 1960s radical activism and his later work in education reform, curriculum and instruction.

In 1969, Ayers co-founded the Weather Underground, a self-described communist revolutionary group that sought to overthrow imperialism. The Weather Underground conducted a campaign of bombing public buildings (including police stations, the United States Capitol, and the Pentagon) during the 1960s and 1970s in response to U.S. involvement in the Vietnam War.

Ayers is a retired professor in the College of Education at the University of Illinois at Chicago, formerly holding the titles of Distinguished Professor of Education and Senior University Scholar.^[ During the 2008 U.S. presidential campaign, a controversy arose over his contacts with then-candidate Barack Obama. He is married to lawyer and Clinical Law Professor Bernardine Dohrn, who was also a leader in the Weather Underground.

Also

William Oscar Ayers (September 27, 1919 – September 24, 1980) was an American Major League Baseball pitcher from Newnan, Georgia. He played for the New York Giants during the 1947 season. (wikipedia)

Interesting concept, but very unevenly developed, and with a high level of thematic density that causes the grid to groan terribly under the pressure. My first thought with the theme was "Why three letters?" and "Why *these* letters?" When the answer ended up being "no reason, totally arbitrary" to both, things got less interesting, and when the final (moving west to east) three themers all ended up having their three letters merely repeated inside of one word instead of strung across two (which is the much much the more interesting / elegant way to do things), well, that was pretty deflating. The revealer felt like kind of an afterthought at that point—not surprising or clever enough to rescue the ho-hum theme execution. At least HANGING INDENT was tough to work out, its three letters doubled across two words and masked by not being doubled in sound. COVER VERSION was likewise an interesting choice here—it's the same sound doubled, but each VER is in a separate word, so the doubleness doesn't announce itself so strongly, and you probably need to get crosses to work it out. Whereas ... MURMUR and BARBARA and TARTARE were all painfully simple to discover because the repeats are such distinctive and obvious parts of these single words/names (esp. MURMUR, the cheapest repeat of them all, and TARTARE, a close second). There's just nothing creative about those last three themers. You'd think a three-letter repeat could've yielded more interesting answers, where the repetition was more disguised and harder to suss out.