Kyle MacMillan
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kyle-macmillan.bsky.social
Kyle MacMillan
@kyle-macmillan.bsky.social
JD/PhD Candidate @ UChicago Law/CS

https://people.cs.uchicago.edu/~macmillan/

202
Govt rushing to adopt AI (nascent and untested) while failing to implement public key infrastructure (mature and battle-hardened) is a puzzle. Perhaps a sign of govt tech/industrial policy shifting from bureaucracy to move fast; break things.
December 11, 2025 at 10:19 PM
There's a saying about how power clouds judgment: the higher you go, the thinner the air. But it's a little on the nose for the president to start saying even crazier things once 35,000 feet in the air.
Trump: AOC is low IQ. If you give her an IQ test, have her pass like the exams that I decided to take when I was at Walter Reed. Those are very hard…

The first couple of questions are easy. A tiger, an elephant, a giraffe..
October 27, 2025 at 2:37 PM
Email sent to UChicago PSD students. An international student was detained and then released by federal immigration officers in Hyde Park.
October 16, 2025 at 5:43 PM
Stress-maxxing my flight by watching Uncut Gems while the guy next to me watches The Hurt Locker
September 17, 2025 at 4:44 PM
that could be anyone
Arenas made a poker table with “ARENAS POKER CLUB” printed on top of it, alongside a a silhouette of a man wearing a No. 0 jersey with “ARENAS” on the name plate, according to federal prosecutors, and sent it to the man the feds say he had rent out his home and set up the events.
July 31, 2025 at 1:19 AM
shot / chaser
May 7, 2025 at 10:44 PM
This figure is kind of side result but is still p noteworthy. I see a lot of claims about opinion length changing over time but (to my knowledge) no one has actually ran the numbers.
CaseSumm is a useful resource for long-context reasoning and legal research:
- Largest legal case summarization dataset
- 200+ years of Supreme Court cases
- "Ground truth" summaries written by Court attorneys and approved by Justices
- Variation in summary styles and compression rates over time
May 1, 2025 at 10:40 PM
Reposted by Kyle MacMillan
🧑‍⚖️How well can LLMs summarize complex legal documents? And can we use LLMs to evaluate?

Excited to be in Albuquerque presenting our paper this afternoon at @naaclmeeting 2025!
May 1, 2025 at 7:25 PM
Reposted by Kyle MacMillan
I'll be presenting this work at 2pm and will be around until Sunday. Please reach out if you're interested in this line of work - would love to connect in person or virtually!

Thank you to my great collaborators @kyle-macmillan.bsky.social , Anup Malani, Hongyuan Mei, and @chenhaotan.bsky.social
May 1, 2025 at 7:25 PM
Reposted by Kyle MacMillan
Although I cannot make #NAACL2025, @chicagohai.bsky.social will be there. Please say hi!

@chachachen.bsky.social GPT ❌ x-rays (Friday 9-10:30)
@mheddaya.bsky.social CaseSumm and LLM 🧑‍⚖️ (Thursday 2-3:30)
@haokunliu.bsky.social @qiaoyu-rosa.bsky.social hypothesis generation 🔬 (Saturday at 4pm)
April 30, 2025 at 8:19 PM
Reposted by Kyle MacMillan
Brilliant (as always) piece by @bridgetfahey.bsky.social on why gov’t control over data is of constitutional moment. Yes it implicates societal and individual privacy concerns but also structural, constitutional grabs of power. Brava. Read www.theatlantic.com/ideas/archiv...
Musk’s Madisonian Insight—And Its Troubling Consequences
The Department of Government Efficiency’s seizure of government databases is not just an act of bureaucratic reorganization. It is an act of constitutional restructuring.
www.theatlantic.com
March 13, 2025 at 7:10 PM
House Republicans defunding the police (as well as schools and emergency services) would be a bigger story if there weren't so much other craziness going on.
NEW in @51st.news: House Republicans just voted to defund D.C. police and schools. As part of a spending bill to avert a federal government shutdown, they could force D.C. to slash $1.1 billion out of its budget, and no one understands really why. 51st.news/house-republ...
Dollars and nonsense: House Republicans vote to defund D.C. police and schools
Congress could force D.C. to cut $1.1 billion out of its local budget, but no one really understands why.
51st.news
March 12, 2025 at 5:14 PM
Walking into majority-undergrad spaces on campus and seeing every third screen with chatgpt open is stunning. Can't imagine the paranoia I'd feel grading.
March 11, 2025 at 8:50 PM
To be clear, this is a congressman from Oklahoma blocking DC from spending over $1 billion of local (not even federal!) funding. Such a blatant attack on our principles of self-governance. If Congress tried this anywhere else there would be riots.
Top House appropriator Rep. Tom Cole just said that the proposal to hold D.C.'s local spending to last year's levels (halfway through a new fiscal year, mind you) amounts to "minor reductions." D.C. officials say there's nothing minor about it: a $1.1 billion cut.
March 10, 2025 at 9:00 PM
Reposted by Kyle MacMillan
OK, I'm starting to get details on what it would mean for D.C. to revert to FY24 spending levels now that we are halfway through FY25. D.C. charter schools would have to cut $165 million. DCPS, $183 million. D.C. Fire, $42 million. MPD, $67 million.
March 10, 2025 at 2:36 PM
In awe of Jayden Daniels. Zen master.
January 19, 2025 at 4:29 AM
Tonight on SNF: Daniel(s) in the Lions' Den
January 18, 2025 at 8:31 PM
I don't use GenAI much but it saved me a ton of time parsing raw HTML today. Wrote briefly:
HTML Parsing with GPT-4o -
GenAI to the rescue
people.cs.uchicago.edu
January 7, 2025 at 10:02 PM
Beyond time for courts / reporters to start numbering by paragraph instead of page. Makes referencing way more consistent. Canada already does this!
January 6, 2025 at 8:20 PM
Reading Marbury for the 3rd time in law school is making me appreciate how much I've learned since the first go round.
January 2, 2025 at 1:53 AM
Terence Tao posted today about paper rejections. He shared this funny story:
January 2, 2025 at 12:53 AM
We didn't look at exactly the same years but observed a similar trend---just a staggering increase in majority opinion word count since the 1960s. (Plot shows 5 yr moving avg 1815-2019)
December 29, 2024 at 3:35 AM
College would have been more fun if people had the good sense to play (the objectively better) When You Were Young instead of Mr.Brightside
December 25, 2024 at 5:03 PM
Unless stress tests are comprehensive, you probably don't want complete transparency because banks might "overfit" to the tests.
Banks Sue Federal Reserve Over ‘Lack of Transparency’ in Stress Testing
The Fed on Monday said it planned to overhaul the stress-test regime for banks and planned to seek public comment on planned changes.
www.wsj.com
December 24, 2024 at 4:31 PM