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Last year, Donald Trump (or, more precisely, Donald Trump’s donors) spent $50 million on legal fees and expenses. This means an estimated 10% of the money he’s raised from his supporters has been going right into some lawyers’ pockets.
Even considering the gouge-happy nature of the legal industry as a whole, that is an unfathomable amount of money. In 2024, as more of the cases concerning the many illegal things Trump has done, sometimes on television, approach trial, that figure is likely to increase substantially.
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Despite this Gatsbyesque spending, Trump keeps losing in court, and losing badly. In a way, it’s perversely inspiring: Trump is well on his way to proving that whether or not a defendant actually engaged in the misconduct alleged may indeed be more important in the justice system than how much money he has.
Trump definitely isn’t getting his money’s worth from most of these high-dollar defense lawyers. A good lawyer will tell hard truths and follow through to make sure a client acts on them. A Trump lawyer will yell at the judge, repeatedly make nonsensical arguments, and call into question the legitimacy of the proceedings because that is what Trump wants, even when it costs him $83.3 million.
Trump does occasionally hire real lawyers. The ones who cannot stand to repeatedly debase themselves leave quickly. The rest continue to make whatever awful arguments he tells them to make, and get raked over the jurisprudential coals for it when the opinions come out.
Many of Trump’s lawyers are probably perfectly happy with this arrangement. No, it does not feel good to lose in court, nor is it fun to have to advance terrible arguments you do not really believe in. But it’s not as though people go into Biglaw as opposed to UNICEF because of their monk-like indifference to material comforts.
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You become a high-dollar lawyer because you want that $2.56 million worth of profits per equity partner. Only, within a big firm, it’s hard to climb over all the other contenders on your way to the top. It’s hard to distinguish yourself with an even stronger work ethic than your peers, or to outshine all of the stiff competition with your brilliance. You’ll certainly make enemies, some of whom will probably become your partners, and thus your eternal albatrosses.
Trump’s lawyers get to skip a lot of the hard Biglaw stuff. They don’t need to navigate complex law firm politics — several lawyers had to leave large firms before taking Trump on as a client, and many of his current lawyers are top dogs at numerically small outfits. His lawyers don’t have to be brilliant — all they have to do is advance whatever dumb arguments Trump wants them to make and then pretend to be surprised when they lose.
They do have to make sure to actually get paid. This is not difficult — a large retainer deposit does the trick — though Rudy Giuliani never figured it out.
They also sort of have to know where the line is and avoid getting sanctioned for crossing it. This one is optional, more of a guideline for representing Trump than an actual rule. For instance, in 2023, Alina Habba was ordered to pay close to $1 million for filing a frivolous lawsuit on behalf of Trump, but since Trump also paid her firm $4.03 million that same year, I’d say she’s doing fine financially.
So, this brings us to the big question when it comes to Trump’s legal team: is the goal here nothing more than a lazy way for a few lawyers to personally enrich themselves with his donors’ money, or are these lawyers actually secret deep state operatives bent on a Joe Biden victory in 2024? Look, I’m no conspiracy nut, but this one makes a lot more sense than Taylor Swift as a CIA asset.
If your goal was to ensure Trump does not get elected to a second term, incinerating tens of millions of dollars of his campaign war chest in exchange for multiple embarrassing losses in court — a rare “double whammy” to use the proper legal terminology — would seem a fairly effective mechanism. And all the while remaining incognito to his supporters because you’re doing exactly as Trump himself instructs!
Either way, perhaps we should thank Trump’s lawyers for their service. I suppose whether they are crippling his campaign financially on purpose or this is only incidental to their greed, the result is the same: a win for American democracy.
Jonathan Wolf is a civil litigator and author of Your Debt-Free JD (affiliate link). He has taught legal writing, written for a wide variety of publications, and made it both his business and his pleasure to be financially and scientifically literate. Any views he expresses are probably pure gold, but are nonetheless solely his own and should not be attributed to any organization with which he is affiliated. He wouldn’t want to share the credit anyway. He can be reached at [email protected].