President Donald Trump has now pardoned three high-profile conservative figures who had been convicted of federal crimes: Joe Arpaio, Scooter Libby, and, on Thursday, Dinesh D’Souza. Shortly after pardoning D’Souza, Trump mused to reporters about more possible pardons or sentence commutations for celebrity pals of his like Martha Stewart and Rod Blagojevich.

It’s likely no coincidence that this is happening while several of Trump’s close associates — namely, Paul Manafort, Michael Cohen, and Roger Stone — are in serious legal jeopardy. Trump has broad pardon powers for federal crimes, even for those who haven’t been charged yet. Now he seems to be trying to send the message that he wouldn’t be afraid to use these powers to protect people who remain loyal to him — people who don’t “flip.”

Yet Trump’s apparent message loses some credibility because, well, he very much hasn’t been willing to actually take that controversial step yet. Four of his former aides have faced charges in Mueller’s probe, three of them have already cut plea deals, and none have been pardoned.

So it’s worth understanding why the president has been hesitant to pull the trigger — because it isn’t as easy for Trump to pardon his way out of the Russia investigation as one might think.

One big-picture reason is pretty simple: Trump clearly thinks that at this point, trying to pardon his way out of the investigation would hurt him more than it would help. It would be a nuclear option, blowing up the political equilibrium on the Russia scandal that has existed since Mueller was appointed last year, with uncertain consequences. (In that, it resembles firing Robert Mueller, Rod Rosenstein, or Jeff Sessions — other actions Trump hasn’t yet followed through on despite his evident interest in them.)

There are practical problems with the pardon strategy too. It doesn’t work for state crimes, it would prevent the pardoned people from pleading the Fifth Amendment in some instances, and Mueller could deem the pardoning itself obstruction of justice on Trump’s part. There’s also the difficult question of when the best time to pardon would be.

Trump may reach the point where he thinks he’s so endangered that he’ll try to pardon his way out of the investigation, despite all these risks. Of late, he appears to be trying to normalize pardons along with discrediting Mueller’s probe politically — both of which could help him get away with pardoning his cronies down the road. Still, he hasn’t reached the point where he’s willing to actually do it yet. Here’s why.

1) Russia-related pardons would mean massive and unpredictable political blowback

Let’s start with the obvious: If Trump pardoned close associates of his who’ve been indicted or are under investigation, it would be an incredibly controversial escalation on his part. The only comparable action of his so far would be the firing of FBI Director James Comey.

Comey’s firing, of course, set off a crisis in the political system that lasted for eight days. Leaks followed one after another, and congressional Republicans struggled with how to respond. The eventual result was the appointment of Mueller as special counsel and a massive expansion of the Russia investigation — in other words, the move backfired.

In the year since then, an equilibrium of sorts has held. Congressional Republicans have generally taken the position that Mueller should be allowed to do his work. Meanwhile, President Trump has insisted on his innocence and repeatedly tried to attack and undermine Mueller’s investigation politically. But he’s shied away from causing another crisis with another major firing, evidently calculating that doing so could cause such blowback that he’d be more hurt than helped by it.

Major pardons would be similar in import. No recent president has used the pardon power to short-circuit a continuing investigation into a major scandal from his administration. Doing so would cause an enormous crisis and send us into uncharted territory. It would be the biggest story in the country. More major leaks would likely pour out from government officials fearing a cover-up. A Democratic takeover of a house of Congress could become more likely, which would mean yet more investigations against the administration.

That’s not to say Trump won’t do it — he fired Comey, after all! But he’s also been hesitant to follow through and cross certain lines, when he or his aides fear that the consequences of doing so would be too severe. So far, at least, a cover-up using pardons is still too far for him to go.

2) Pardons bring Fifth Amendment complications

The political blowback isn’t the only problem. There are several practical reasons pardons wouldn’t be as effective a way for Trump to shut down the Russia investigation as one might think. Let’s start with the Fifth Amendment issue.

If Trump does pardon people, those people could then be asked to testify under oath, either by Mueller’s team or by Congress. Pre-pardon, they could have pleaded the Fifth, refusing to answer on certain issues on the grounds that they might incriminate themselves. But if they’ve been pardoned already for those matters, they’re no longer at risk of incriminating themselves — so they’d have to testify truthfully, or risk new charges for contempt or lying under oath.

You see the problem: If somebody takes a pardon to avoid telling prosecutors what they know about Trump, that person could later be compelled to ... tell prosecutors what they know about Trump.

However, Trump could theoretically pardon those new charges too. And as my colleague Sean Illing has written, the exact implications for a pardon on Fifth Amendment rights depend on what, exactly, the pardon is for.

For instance, if Trump pardoned Manafort on specific tax and bank fraud charges, Manafort could still theoretically plead the Fifth on topics related to potential criminal collusion. But if Trump issued a “blanket pardon” for “all offenses” between certain dates like President Ford did for Richard Nixon, then that person would seemingly lose their right to invoke the Fifth for any events in that time span. So Trump would face a trade-off between maximally protecting his associates from legal jeopardy while still protecting their rights to plead the Fifth.

3) Presidential pardons don’t work for state crimes

There’s also the potential problem that President Trump only has the power to pardon federal crimes, not state or local crimes.

Certain potential crimes relevant to Trump associates, like bank fraud, violate both federal and state law. So, theoretically, if state prosecutors went after Trump associates on state charges — as many have speculated could happen to Paul Manafort or Michael Cohen — the president wouldn’t be able to protect them with pardons.

Whether the state prosecution option is available will depend on what the specific crimes are and what state they were allegedly committed in. One issue is that New York state currently has a “double jeopardy” law on the books that would prevent someone from being tried for a state crime if they’ve already been tried for the same crime federally. (Some legislators are discussing changing the law, but they have not done so yet.)

Still, the potential for state charges is one consideration that might lead some Trump associates to cooperate and strike a plea deal rather than hold out for a pardon — because the pardon can’t protect them from everything.

4) Pardons could put Trump in more obstruction of justice peril

This March, Trump’s lawyers assembled a list of potential questions they thought Mueller wanted to ask the president, based on their conversations with the special counsel’s team. And one of those was specifically about pardons:

After the resignations, what efforts were made to reach out to Mr. [Michael] Flynn about seeking immunity or possible pardon?

Mueller’s team is investigating Trump for, among other things, obstruction of justice. This intriguing inclusion suggests they may consider Trump’s use or discussion of pardons for people he fears might flip on him to itself be a form of obstruction.

Indeed, NBC News reported in April, citing three sources familiar with the investigation, that Mueller has collected information on “Trump’s dangling of pardons before grand jury witnesses who might testify against him.” And Trump’s former lawyer John Dowd reportedly discussed potential pardons with lawyers for both Manafort and Flynn last year. (Flynn has since struck a plea deal with Mueller.)

Trump’s team would likely respond that he’s well within his presidential powers to pardon, or consider pardoning, anyone he wants. But some legal experts think that this could still be obstruction of justice if done with corrupt intent. In any case, it’s clear that pardons aren’t legally cost-free for Trump because they could well make his own obstruction problems with the special counsel even worse.

5) There’s no good time to do it

Back in May 2017, President Trump gave an interview to NBC’s Lester Holt that was mostly noted for his admission that the Russia scandal was on his mind when he decided to fire Comey.

He had one more telling line. He said, with emphasis, that after he made up his mind to fire Comey, he knew “there was no good time to do it!”

The timing is a major problem with pardoning Russia scandal figures as well. For all the reasons stated above, these pardons could end up putting Trump’s presidency at serious risk.

Speaking pragmatically, the ideal time for a president to pardon his cronies or allies is when he is about to leave the presidency. President George H.W. Bush pardoned key figures in the Iran-Contra scandal in December 1992 — after he had already lost reelection to Bill Clinton. President Clinton controversially pardoned Marc Rich, whose ex-wife was a major Democratic donor, only hours before his second term in office ended. In both cases there was outrage, but both presidents were already headed out the door, so what did it matter?

But President Trump has only been in office for 16 months. Explosive Russia-related pardons before the midterms this year are clearly a bad idea, as they could badly hurt Republican candidates and saddle Trump with an adversarial and investigation-hungry Democratic Congress. After the midterms, then, Trump’s own reelection looms, and corrupt pardons would put that in danger.

Maybe Trump would be ready to pull the trigger after the 2020 election, either if he’s defeated and has nothing more to lose or if he wins and feels vindicated by public opinion. Alternatively, if he does win a second term, he’d probably want to serve it out and accomplish things without being impeached.

Yet November 2024 will look far away indeed for Mueller’s targets, who will be saddled with enormous legal bills and could be convicted and serve hard time well before then. They’d have to be willing to rely on the word of Donald Trump that they’ll be taken care of ... eventually. When it’s convenient for him. And how comforting is that?