From Kasparov's Next Move <[email protected]>
Subject Trump’s Secret to Limiting Free Speech Without Outlawing It
Date July 9, 2025 9:15 PM
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From the very first chants of “lock her up” [ [link removed] ] on the 2016 campaign trail, Donald Trump has never been above threatening his opponents with a little persecution. Nine years later, we’re well past chants. Today, it was reported that Trump’s Department of Justice is investigating former FBI Director James Comey and former CIA Director John Brennan. The scope of the inquiry, apparently related to the Trump-Russia probe, remains unclear, but given that both men are vocal critics of the president, it’s not a stretch to conclude that the probe is politically motivated. Trump, ever wanting for new adjectives, labeled his latest targets “crooked as hell.” [ [link removed] ]
This sort of news naturally conjures up images of dictators throwing their opponents in jail. Trump isn’t a dictator of course, but he has shown he will do a lot to hold onto power. He is an unpredictable, ego-driven man surrounded by loyalists and sycophants who happens to be the most powerful person on earth. It’s a dangerous combination, so we can’t entirely discount the possibility that Comey and Brennan end up doing hard time (On this question, President Trump has said that “whatever happens, happens”).
Still, I’d like to propose an alternative trajectory for these developments. The scenario I’m predicting is no less sinister than going straight to jailing dissenting voices. It is, however, more subtle—surprising, given that Trump is anything but. Yet take it from a Russian—this is how even the most bombastic authoritarians start off.
What do I see happening?
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Instead of looking to jail his rivals, Trump is simply going to make their lives infinitely more difficult.
Fighting a frivolous DOJ investigation means Comey and Brennan’s first challenge will be finding serious legal representation. This may prove more difficult than before given Trump’s executive orders targeting his enemies in big law. Some top firms have already acquiesced to the administration and those that haven’t may not want to invite new headaches. Now, America is not Russia (yet), and someone will certainly represent Comey and Brennan. But you can bet they won’t be cheap.
Like many former senior government officials, Comey and Brennan are well off, but they are not among the nation’s über-rich like Musk, Zuckerberg, Bezos, and arguably Trump himself. In retirement (in Comey’s case, forced retirement), let’s assume that they can earn two-to-four million dollars a year from five- and six-figure speaker fees and consulting gigs. Comey reported a net worth [ [link removed] ] of $11 million before taking up his post as FBI chief a decade ago. That’s an incredible amount to most Americans, but it’s not an endless pit of money. And legal costs alone will likely end up totaling hundreds of thousands, if not millions, of dollars. Meanwhile, Trump has the essentially unlimited resources of the federal government at his disposal.
A protracted legal battle will steadily sap resources away from Comey and Brennan. And so far, we have only accounted for direct losses. The indirect costs could be far greater. They will both be marked men. Who will want to work with them if it means risking the ire of the president of the United States? James Comey and John Brennan may find themselves isolated in ways they’ve never experienced before. Others will get the message: If the president can go after the heads of America’s most storied intelligence agencies, he can go after you too. People who would have considered speaking out before will decide it’s not worth the dangerous inconvenience. You don’t need to go after hundreds or thousands of people to achieve this chilling effect. Just as Trump made an example of Harvard and Columbia [ [link removed] ], he will make an example of these two men. This is how you limit free speech without actually outlawing it.
If this saga does end with the DOJ putting Comey and Brennan in jail, that might prove to be a bridge too far. If you thought there was outrage over ICE’s politicized arrests of non-citizen students with non-mainstream views, wait until Trump tries to lock up the former directors of the FBI and CIA. It will be 24/7 headline news. There will be massive protests. Congressional Democrats will be forced out of their stupor and Capitol Hill will be bogged down in hearings (OK, on this last one, I’m not holding my breath! [ [link removed] ]).
If, however, Trump stays the course and just hassles Trump and Comey into submission, the story may pass unnoticed. As of this writing, media coverage has been delayed and spotty. It’s a damaging blindspot that will come back to haunt us.
People the world over know that Vladimir Putin is behind the murder of Alexei Navalny, Boris Nemtsov, and Anna Politkovskaya. Far fewer recall his first years in the Kremlin. How invasive audits [ [link removed] ] rendered civil society groups powerless. The prosecutor-general’s office issuing summonses to independent media [ [link removed] ]. Selectively revoking official immunity [ [link removed] ]. These incidents of procedural harassment are not memorable flashpoints like high-profile arrests or assassinations. But they are a slow-acting poison that can weaken the opposition without waking up the public. Learn to recognize these tactics before a wannabe strongman lulls you to sleep.
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