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Simpson Thatcher

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Simpson Thacher & Bartlett LLP, a major international law firm, has recently been the subject of controversy due to its dealings with the Trump administration.

Here's a breakdown of the situation:

In essence, Simpson Thacher's decision to engage with the Trump administration sparked controversy and had consequences for the firm's reputation and client relationships.

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in April, the nine Biglaw firms who settled with the Trump administration to the tune of a combined billion in pro bono payola received inquiries from legislators over the legal and ethical problems raised by the deals. Essentially, how can the firms remain adamant that they did nothing to merit a retaliatory executive order — in the case of most firms, before any such order even existed — and claim that the deal is anything but an ethical compromise to illegal government extortion?

It’s one thing to settle “without admitting or denying” a violation, and it’s another to bind firm operations to the government over violations that never even materialized.

On May 6, the Bulwark reported on some of the firms’ responses to inquiries from Sen. Richard Blumenthal and Rep. Jamie Raskin that more or less boiled down to “LOL, what pro bono deals?” and furiously backpedaling that they’d given the administration anything at all. As they described it, they promised Trump nothing more than pro bono work they already planned to do and will not serve at the whim of the administration even if Trump publicly says that’s the deal and issued an executive order explicitly deputizing the firms to work on police brutality defense. But the firms implied that they would simply not abide by such a request from the government.

Yeah, let’s see how that goes for you when you tell Trump you’re not giving him what he bargained for.

Another query, spearheaded by Rep. David Min and Rep. April McClain Delaney, also sought answers from the Orange Shoe firms, seeking more depth, specifically asking the firms to repudiate the deals on the grounds that such a deal:

(1) is unenforceable under contracts law; (2) would have enormous negative impacts on the legal system; (3) could potentially expose your firm and its attorneys to civil and criminal liability under state and federal law; and (4) creates potentially irresolvable violations of applicable Rules of Professional Conduct with respect to conflicts of interest and limiting an attorney’s future practice of law

Business Insider collected all nine May 8 responses to the Min and Delaney inquiry and while they largely reiterate the “LOL, wut” response previously reported, the letters offer a more comprehensive view of how these firms spin the unspinnable. Some are curt and insultingly dismissive of congressional inquiry. Others go into some detail with their “non-denial denials.” And yet none actually, you know, answer the questions.

When we say, “curt and insultingly dismissive,” we mean a response like this one from Quinn Emanuel representing Milbank:

On April 2, 2025, Milbank’s Chairman sent an internal email to firm personnel concerning the Agreement. That communication was picked up by the American Lawyer and continues to be available online. We respectfully refer you to that message…

They told congressional representatives that they wouldn’t answer their questions but they could go get an American Lawyer subscription and check out a reprinted email to staff. First of all, if it helps, we also reprinted the email at Above the Law and we aren’t behind a paywall. You’re welcome. Second, they told congresspeople that they weren’t going to answer their specific questions and to look it up on Law.com! Assuming for the sake of argument that the email directly addressed all of the questions posed — it doesn’t — how hard is it to copy and paste? Does Quinn Emanuel charge so much by the hour that Milbank can’t afford to have the email turned into a letter?

Simpson Thacher also referred the legislators to an email but had the common courtesy to at least attach a printout of the American Lawyer article. Though, again, why not just include the email? Presumably Simpson still has custody of their own email… why post an article about the email? Do they think it lends credibility to say, “Hey, here’s an internal email that our lawyers are so fucking furious about that they leaked it to the press”?

Because it doesn’t really.

As an aside, the funniest part of Simpson using a printout of the American Lawyer story is that the last line is orphaned onto the next page, requiring them to include this…

[email doc]

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We’ve called them cowardly and collaborators and capitulators and Trump’s deputies. We’ve characterized their actions as surrendering, bending the knee, and swearing fealty to the administration. We’ve branded them the Order of the Obsequious and bandied about the Deep Mistake Nine for the nerd crowd. We even tabbed them “yellow-bellied” for an 1800s grizzled prospector vibe.

The individual firms earned some new nicknames too. “Paul Wuss” caught fire on social media (sorry, the proper styling is “Paul, Wuss”), but we heard WillkieFear and Cowardalader too.

For the purposes of news coverage, we can and do lean on our thesauruses to keep articles from getting bogged down in convention. Spicing new phrases or nicknames into stories helps keep them fresh. But maybe there’s a value in settling on a stable, catchy moniker — at least for some constituencies.

Mostly, I’m thinking about law school students. When they start signing up for on-campus interviews — to the extent they still exist — what’s the best way to describe the new category of law firm willing to shell out some pro bono payola to avoid having to take Donald Trump to court?

I remember first applying to law firms and being schooled by classmates on “the tobacco firms” that everyone was supposed to avoid. It proved useful to have a handy, descriptive title to work with as we signed up for interviews. Sometimes we forget that law students aren’t necessarily as steeped in firm news as practitioners and it’s essential to develop quick points of reference that can stick in a student’s head.

A reader recently pitched the term “Orange Shoe” — a twist on the traditional “White Shoe” classification — which is absolutely fantastic. But it got me thinking that these naming exercises are more than whimsical rebranding, but a valuable sorting device for young future lawyers trying to wrap their heads around hundreds of firms. They’re talking about White Shoe firms among their friends, why not bootstrap off that classic terminology to capture the essence of prestigious firms willing to sell out rather than stand up for themselves.

After all, if your goal is to one day uphold the rule of law, maybe don’t start your career at a firm agreeing in principle to lend its talents to support the administration rewriting it with a Sharpie. Even if the firms are furiously trying to downplay the scope of the deals… we’ll see what Trump thinks about that. Anyone old enough to remember the Star Wars movies before they started to suck knows exactly how that negotiation is going to go.

And it’s a useful way to think about these firms beyond cowardice and complicity — ooh, there’s another good one! Even if a student wanted to give the firm the benefit of the doubt and doesn’t per se begrudge the firms that they HAD to settle with Trump, “Orange Shoe” as opposed to a more value-laden term conveys a firm that thought its business was so intertwined with staying in line with the administration’s interests that it needed to cave. That means a student might not want to hitch their future to that mix of work in any event.

Or maybe Orange Shoe isn’t the answer. What other names have you heard that you like — either for the category of nine who explicitly agreed to payola deals, the broader category of firms either surrendering or preemptively throwing DEI and pro bono work under the bus to avoid Trump’s attention, or for individual firms involved. Hit us up at tips@abovethelaw.com (don’t worry, you’re anonymous) and don’t forget to tag us on social media if you see a good name in the wild (abovethelaw.com at Bluesky, atlblog on Twitter).

If we get enough of these together, maybe we’ll invite some audience participation to decide which one should become the industry standard.

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[### Microsoft Drops Law Firm That Made a Deal With Trump ...

The New York Times

https://www.nytimes.com › 2025/05/01 › business › mi...](https://www.nytimes.com/2025/05/01/business/microsoft-drops-trump-compliant-law-firm.html)

May 4, 2025 — Simpson Thacher reached a deal with the White House last month in which the firm committed to perform $125 million in free legal work for causes ...

[### Simpson Thacher Lawyer Quits as Firm 'Capitulates' to ...

Bloomberg Law News

https://news.bloomberglaw.com › business-and-practice](https://news.bloomberglaw.com/business-and-practice/simpson-thacher-lawyer-quits-after-firm-capitulates-to-trump)

Apr 11, 2025 — A Simpson Thacher & Bartlett associate quit his job after the law firm reached a deal with President Donald Trump to provide $125 million in ...

[### Statement: Microsoft's Decision To Drop Law Firm Makes ...

Demand Justice

https://demandjustice.org › statement-microsofts-decisio...](https://demandjustice.org/statement-microsofts-decision-to-drop-law-firm-makes-clear-that-capitulating-to-trump-does-not-get-you-rewarded/)

May 1, 2025 — Simpson Thacher alone pledged $125 million in pro-bono services to appease Trump, part of the almost $1 billion pledged overall by nine firms ...

[### Simpson Thacher deal with Trump is 'shortsighted,' ...

Business Insider

https://www.businessinsider.com › Law › Politics](https://www.businessinsider.com/simpson-thacher-big-law-trump-deal-siunik-moradian-resignation-2025-4)

Apr 12, 2025 — The law firm Simpson Thacher & Bartlett made a deal with Trump to avoid a punitive executive order. The firm joins a growing list of law ...

[### Microsoft drops a law firm that appeased Trump, hires ...

MSNBC News

https://www.msnbc.com › maddowblog › microsoft-dro...](https://www.msnbc.com/rachel-maddow-show/maddowblog/microsoft-drops-law-firm-appeased-trump-hires-firm-s-fighting-trump-rcna204152)

May 1, 2025 — About a week ago, attorneys at one firm — Simpson Thacher & Bartlett, which recently reached an agreement with Trump and his team — informed ...

[### Trump's Biglaw Bootlickers Say Quiet Part Out Loud In ... Above the Law

https://abovethelaw.com › 2025/05 › trumps-biglaw-boo...](https://abovethelaw.com/2025/05/trumps-biglaw-bootlickers-letters-to-congress/)

8 days ago — Simpson Thatcher* also referred the legislators to an email but had the common courtesy to at least attach a printout of the American Lawyer ...

[### Law firms' deals with Trump roil their staff, deepen industry ...

Reuters

https://www.reuters.com › legal › government › law-fir...](https://www.reuters.com/legal/government/law-firms-deals-with-trump-roil-their-staff-deepen-industry-rifts-2025-04-14/)

Apr 15, 2025 — Law firms that have pledged $940 million so far in free legal work and made other concessions to US President Donald Trump are facing a backlash from some of ...

[### Kirkland And Simpson Turned To Major Trump Fundraiser ... Above the Law

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Apr 24, 2025 — Kirkland and Simpson Thacher each paid Ballard $100,000 for lobbying work on their firm's behalf in the first quarter of this year, according to ...

[### Big Law firms double down on their Trump deals in letters ...

Business Insider

https://www.businessinsider.com › Law › Politics](https://www.businessinsider.com/big-law-trump-deals-legal-congressional-letters-2025-5)

May 21, 2025 — Firms like Simpson Thacher and Skadden pushed back on Democrats' claims that their Trump deals amounted to illegal bribes.

[### April 18, 2025 VIA EMAIL Alden Millard Chair of the ...

U.S. House Judiciary Committee Democrats (.gov)

https://democrats-judiciary.house.gov › 2025-4-1...](https://democrats-judiciary.house.gov/uploadedfiles/2025-4-18-blumenthal-raskin-letter-to-simpson-thatcher-002.pdf)

PDF

Apr 18, 2025 — We write today regarding President Trump's April 11, 2025 announcement that Simpson. Thacher & Bartlett LLP (“Simpson Thacher”) reached an ...

5 pages

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