Will the Trump-Musk relationship last?

It might help to look towards history.

Good morning! It’s Tuesday, February 11, 2025. Election Day 2025 is 267 days away. Election Day 2026 is 631 days away.

As you all know, the topic I’ve been tracking most closely these past few weeks has been how our system of checks and balances is faring in the Trump era — watching especially, in the last few days, the push-and-pull between the Trump administration and the federal judiciary.

Shortly after yesterday’s newsletter went out, the highest-profile test in this arena yet arrived when U.S. District Judge John McConnell issued an order finding that the administration had continued to withhold certain funds in violation of his previous order blocking their attempted funding freeze. (The administration had argued that the funds in question were not impacted by McConnell’s previous order.) McConnell ordered the administration to “immediately restore withheld funds” and “end any federal funding pause” that had been in effect.

The administration has appealed the case to the circuit court level — as is their right — and asked both the district and circuit courts to pause McConnell’s order, arguing that it represented an “extraordinary and unprecedented assertion of power by a single district court judge.” But we have yet to receive an answer to the crucial question: If the order remains in place, does the administration plan to comply with it?

Meanwhile, Trump’s team continued running up losses in court Monday, as a pair of judges paused changes to the National Institutes of Health and the firing of a government ethics official, and a third judge extended his block on the administration’s “buyout” offer.

Separately, two unions filed a motion alleging that the Trump team had not brought all U.S. Agency for International Development (USAID) employees back from administrative leave, as a judge had ordered. This could likely form the next test of the administration’s compliance with judicial orders.

One last note. Last week, I wrote that Trump and Elon Musk’s aggressive speed may be their undoing, not only because federal law prohibits “arbitrary and capricious” administrative actions but also because courts generally frown upon changing stories and sudden reversals, which are foundational the Trump/Musk operating style.

We received more examples of that on Monday, as administration lawyers admitted making significant errors in previous filings in the USAID case and the case on Treasury Department data. At another court hearing, litigants cited a Musk tweet to help build their case, proving once again that his frequent and chaotic posting will not help his legal odds.

With that, it’s time for today’s main event. I always want to make sure WUTP is focusing on the issues you are wondering about — and the best way to do that is to ask you directly. Let’s get to some of your questions:

DocOnTheRange asks: I always appreciate your connections between historical and current events, I would love to hear your take on if a Musk-like agent has precedent. Didn’t JFK use his family to check in on the Navy during the Cuban Missile Crisis to ensure they were following orders? Woodrow Wilson’s wife more or less took over after his stroke… I am guessing there are other times presidents have used unofficial agents as well.

I love this question. While every president relies on counsel from a mix of advisers, many have also had that one confidant who seems to be trusted above all others, even if their place on the White House org chart is unclear (often to the official staff’s annoyance). Sometimes, as with Bill Clinton’s friend and fixer Vernon Jordan, they operate completely outside of government. Other times, as with Harry Hopkins — who was known as the “co-president” for his role managing several wartime agencies under FDR — their titles underrate the true extent of their authority.

As the question notes, there are presidential relatives who have fallen into both of these categories over time, from Edith Wilson to Bobby Kennedy. (Technically, there is no government role known as “First Lady,” so in a way all presidential spouses are “unofficial agents” when advising on policy. Kennedy served as his brother’s attorney general, but advised on much more than simply legal matters.)

It’s also important to point out that, for much of U.S. history, the White House budget was a lot smaller, so it was the norm for presidential advisers to be more “unofficial agents” than formal staffers. Figures in that category have included quite a few people who might surprise our modern sense of ethics, from members of the media (journalist Francis Preston Blair was a key member of Andrew Jackson’s “Kitchen Cabinet” of outside advisers; Washington Post editor Ben Bradlee was famously friends with JFK) to Supreme Court justices (Abe Fortas attended staff meetings at the Lyndon Johnson White House).

In terms of Musk’s specific background and amount of influence, however, two historical figures jump out to me as parallels: Mark Hanna, during William McKinley’s administration, and Edward House, during Woodrow Wilson’s.

Neither Hanna nor House were the richest man in the world at the time they advised the president — but both were wealthy business titans who plowed significant resources into helping McKinley and Wilson, respectively, become president. After the elections, they were rewarded with positions of singular influence.

“I want you as one of my chief associates in the conduct of the government,” McKinley wrote to Hanna. “Mr. House is my second personality. He is my independent self. His thoughts and mine are one,” Wilson said of House.

Hanna and House both turned down offers of Cabinet positions, but like Musk, they didn’t need a specific administration title to wield power. Hanna became a U.S. senator (taking the seat vacated by McKinley’s secretary of state, in an arrangement that raised some eyebrows) and House became known — literally — as Wilson’s “executive agent,” boasting a broad and varied portfolio. (Musk’s governmental title is not known. On his X bio, he is listed as “White House Tech Support.”)

Both played key roles in staffing the resulting administrations: Hanna dispensed fistfuls of patronage jobs; House was said to have selected most of the Cabinet. They advised the president on all manner of issues, especially foreign policy. Some lawmakers referred to the Panama Canal as the “Hannama Canal” because Hanna was so persistent in pushing for it. (Trump and Hanna would have gotten along.) House was Wilson’s key liaison to the peace negotiations during World War I, a task almost as complicated as fostering “government efficiency.”

Just as Musk is apparently sleeping in the Eisenhower Executive Office Building (right next to the White House), House lived in the White House for stretches of Wilson’s presidency. Hanna was offered similar quarters; he declined, but didn’t stray far from the president’s side either — he moved right across the street, into a residence that became known as the “Little White House.”

As influential as House and Hanna were, Musk — as ever — is moving to assume a position even larger than his 20th century counterparts. If he is successful in his stated goals of slashing the federal budget and bureaucracy, he will have left an imprint on the U.S. government that neither House nor Hanna could have dreamed of.

But the House and Hanna stories also share strikingly similar endings, both of which serve as cautionary tales for Musk. In both cases, they started out as subordinates and eventually grew beyond their britches. When House began making compromises during the World War I peace talks that went beyond what Wilson had authorized, the president was furious, as Gary Ginsberg — author of a great book on presidential friends — recently wrote in the Washington Post:

Worse, [House] bragged to the press about what he’d done. When newspaper articles credited House for helping secure an agreement, the president decided he’d had enough. The night the Treaty of Versailles was signed, Wilson coldly said “Goodbye, House” as he boarded the train to begin his return to the United States. They never spoke again.

McKinley and Hanna went through a similar falling out. When it was time for McKinley to launch his re-election bid, he waited months before announcing whether Hanna would be appointed as campaign manager, reportedly giving Hanna so much stress that it led to him having a heart attack.

The reason for the delay is unclear, but historians have suggested that the president was displeased about “Hanna’s growing— and separate—status as a national political figure in his own right,” as Hanna biographer William Horner put it. Horner also cites another scholar who noted Hanna’s frustrating “propensity to speak for the president whenever he felt enthusiastic about something, whether he was authorized to do so or not. Hanna was eventually given the job, but his influence faded significantly in McKinley’s second term, which was ultimately cut short by an assassin’s bullet.

It’s far too early to say whether the Trump-Musk relationship will end up like its two predecessors. One key difference is that Musk is essentially starting as a free agent, rather than growing to become one. Musk could benefit from the fact that his independent status has been baked into the dynamic since Day One — or it could just hasten his demise. Musk, it should be noted, also has more money and more access to an outside megaphone than either House or Hanna.

But, at the end of the day, there is only ever one president — a lesson that revisiting past presidential advisers can remind us. House and Hanna both learned that the hard way; the jury is still out on their modern-day successor.

An 1890s political cartoon depicting a tiny William McKinley sitting inside Mark Hanna’s giant palm.

A few more questions

Hope asks: Run down on ‘special government employees’? Never heard of this before?

For those unaware, the White House said last week that this was the designation being given to Musk (and a few other DOGE staffers). The idea originally comes from a 1962 law, which explains it this way:

The term ‘special Government employee’ shall mean an officer or employee of the executive or legislative branch of the United States Government, of any independent agency of the United States or of the District of Columbia, who is retained, designated, appointed, or employed to perform, with or without compensation, for not to exceed 130 days during any period of 365 consecutive days, temporary duties either on a full-time or intermittent basis.

SGEs were intended for exactly this purpose: to allow experts from the private sector to come into the government for a short amount of time. (As you’ll see from the statute, the job comes with a 130-day expiration date.) SGEs still have to file financial disclosure reports — but those reports only become public if the SGE takes a salary, which Musk isn’t.

Like other government employees, SGEs are not allowed to participate in matters that directly affect their financial interests, but they can receive a waiver removing that prohibition. Previous SGEs have generated controversy for their awkward existence at the intersection of the public and private sectors, including Hillary Clinton aide Huma Abedin and Biden adviser Anita Dunn.

Larry Beckett asks: If these egregious, clearly unconstitutional actions by Trump and his co-president continue do you see any chance that that the US Supreme’s will deem them unconstitutional?

Like with any president, the Supreme Court will rule for Trump sometimes and against Trump sometimes. Trump, obviously, comes in with an advantage — not because he appointed one-third of the court and therefore they owe him personally, but because he appointed one-third of the court and therefore many of the justices align with him ideologically (specifically on questions of executive power).

But, as I’ve written before, the Supreme Court’s conservative wing is more nuanced than it’s sometimes depicted — including all three Trump-appointed justices, each of whom have interesting idiosyncrasies and very much do not always vote as a bloc. Ironically, if anything, the Trump-friendliest justices have tended to be Clarence Thomas and Samuel Alito, both of whom were on the bench long before Trump took office; Trump appointees Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett are each much more likely, depending on the type of case, to defect from the standard conservative position. (Chief Justice John Roberts is by no means a guaranteed Trump vote on many cases either.)

In Trump’s first term, this could be seen on a slew of matters involving him personally — with the court’s refusal to engage in his 2020 election fraud claims perhaps the highest-profile example. As I noted recently, in his first term, Trump was the only president since World War II to lose at the Supreme Court more often than he won. Anyone who is saying that the court will not, on at least some cases, rule against Trump’s actions is not engaging with the actual evidence of what happened last time.

Denise Jacobson asks: Even if the courts try to stop Musk et al, and they choose to ignore them, then what happens?

Intriguingly, Chief Justice Roberts wrote about this possibility in his annual year-end report just two months ago (emphasis mine):

It is not in the nature of judicial work to make everyone happy. Most cases have a winner and a loser. Every Administration suffers defeats in the court system—sometimes in cases with major ramifications for executive or legislative power or other consequential topics. Nevertheless, for the past several decades, the decisions of the courts, popular or not, have been followed, and the Nation has avoided the standoffs that plagued the 1950s and 1960s. Within the past few years, however, elected officials from across the political spectrum have raised the specter of open disregard for federal court rulings. These dangerous suggestions, however sporadic, must be soundly rejected.

But Roberts does not answer the question of what would happen if those “dangerous suggestions” are carried out — perhaps because there is no answer. The legislative branch does have one remedy against a hypothetical lawless president: impeachment, although recent history has proven it to be more of a partisan tool than an effective accountability mechanism.

The best the judicial branch can do is hold an executive branch official in contempt — something Judge McConnell, of the funding freeze dispute, seemed to flick at with a citation in his Monday order. (“Persons who make private determinations of the law and refuse to obey an order generally risk criminal contempt even if the order is ultimately ruled incorrect.”)

But, ultimately, the group charged with carrying out a judicial contempt citation is the U.S. Marshals Service, which sits in the executive branch and ultimately reports up to the attorney general and then the president. This is the conundrum with having one branch that interprets the laws and another one that enforces them — a division of powers that looks genius and seamless right up until it isn’t — and it’s why I’ve written that any sort of scenario where a president refuses to comply with court orders would launch us into a constitutional crisis.

At that point, the outcome would essentially come down to who the Marshals Service and other law enforcement agencies (potentially including the military) decide to listen to, hardly a happy place for a democratic republic to be.

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Thanks so much to everyone who sent in questions! I still have a bunch more to get to, so stay tuned. And keep sending questions in to gabe@wakeuptopolitics.com or using Substack Chat.

Many Substack writers like to put their mailbag pieces beyond a paywall — but at least so far, I’ve chosen not to, operating under the logic that if some readers are wondering about the answer to a question, other readers probably are too.

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More news to know

Director of National Intelligence nominee Tulsi Gabbard in 2024. (Photo by Gage Skidmore)

President Trump signed executive orders imposing 25% tariffs on all steel and aluminum imports on Monday, reviving an action that raised prices during his first term. China’s retaliatory tariffs against the U.S. also went into effect.

The Senate voted 52-46, along party lines, to advance Tulsi Gabbard’s controversial nomination to be Director of National Intelligence.

Trump threw a wrench into an existing dispute between Israel and Hamas about the status of their ceasefire, announcing that “all hell” would break loose if Hamas doesn’t release all the remaining Israeli hostages by Saturday, weeks before the deadline set by the deal. He also suggested that Palestinians wouldn’t be allowed to return to Gaza under his planned U.S. takeover of the territory.

Candidates for Trump administration national security jobs are reportedly being asked if January 6th was an “inside job.” (It wasn’t.) Answering “no” can hurt an applicant’s prospects. Meanwhile, Trump appeared to suggest in a Fox News interview that there was voter fraud in the 2024 election, which he won. He offered zero evidence.

Hours after pausing enforcement of an anti-bribery law, Trump offered relief to two Democrats accused of bribery, pardoning former Illinois Gov. Rod Blagojevich (who tried to sell a U.S. Senate seat) and dismissing charges against New York City Mayor Eric Adams (who was indicted for accepting perks from Turkish officials in exchange for political favors).

The Consumer Financial Protection Bureau is mired in confusion after the agency’s new acting director ordered employees to stop their work.

Some diplomats are expressing concern about the 19-year-old Musk acolyte Edward Coristine being hired as a State Department senior adviser. Coristine uses the nickname “Big Balls” on his online accounts.

While reviewing documents slated to be released under a Trump executive order, the FBI discovered 2,400 records tied to JFK’s assassination that were never provided to the National Archives as they were supposed to.

Defense Secretary Pete Hegseth signed a memorandum changing the name of North Carolina’s Fort Liberty back to Fort Bragg. But this time it will honor Pfc. Roland L. Bragg, a World War II hero, not Braxton Bragg, the Confederate general.

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The day ahead

Trump and King Abdullah II in 2017. (Photo by the White House)

• President Trump will meet with Jordan’s King Abdullah II, one day after suggesting that he may withdraw aid from Jordan and Egypt if they don’t take in Palestinians as part of Trump’s plan to rebuild Gaza. Later in the day, Trump will sign executive orders.

• The Senate will continue consideration of Tulsi Gabbard’s nomination to be Director of National Intelligence. Unless an agreement is reached, a vote on Gabbard’s confirmation will be held shortly after midnight, followed by a procedural vote on Robert F. Kennedy Jr.’s nomination to be Secretary of Health and Human Services.

• The House will vote on a resolution to unlock consideration of the Midnight Rules Relief Act, which would allow Congress to more easily undo regulations that were submitted in the last 60 legislative days of an outgoing president’s term.

• The Supreme Court has no oral arguments this week.