Will Trump Pardon Martha Stewart? The Two Of Them Go Way Back

Donald Trump may have soured many a friendship in recent years, but his latest announcement might get him back in a former pal's good books. On Thursday, Trump said he's considering pardoning Martha Stewart, who was investigated for insider trading in the early 2000s and later convicted for related crimes.

Trump's announcement came hours after he tweeted that he had pardoned Dinesh D'Souza, a right-wing figure who's peddled conspiracy theories and was convicted of campaign finance fraud. According to CNN, Trump told reporters on Air Force One on Thursday that Stewart was "to a certain extent... harshly and unfairly treated." She was convicted in 2004 of obstruction of justice, conspiracy, and lying to investigators. (Stewart was prosecuted by none other than James Comey, whom Trump fired as FBI director and has publicly insulted on Twitter many times.)

Aboard Air Force One, Trump also said that he's thinking of commuting former Illinois Gov. Rod Blagojevich's sentence. Blagojevich was convicted of corruption charges and was slapped with a 14-year sentence.

The collection of people convicted of crimes that Trump wants to pardon (or already has) may seem random, but Stewart, Blogojevich, and D'Souza are connected to the president in some way.

Trump and Stewart have a complicated history. They were friends at one point, before falling out over The Apprentice. In 2005, Stewart hosted an Apprentice spinoff that got low ratings, and she claimed Trump had walked back on his deal to step down from his show so only her version of the show would air at the time. "If I'd had my druthers, there would have been only one Apprentice on the air at one time," she said at the time.

Trump responded to Stewart's diss with a letter that referenced her insider trading scandal, accused her of making up the deal for him to step down from the show, and slammed her ratings. "Your performance was terrible in that the show lacked mood, temperament and just about everything a show needs for success," Trump reportedly wrote in the letter. "I knew it would fail as soon as I first saw it — and your low ratings bore me out."

Stewart said, according to CNN Money, that the letter was "so mean-spirited and reckless that I almost can't believe my longtime friend Donald Trump wrote it."

As for Blagojevich, he was a participant on Celebrity Apprentice back in the day. The official who prosecuted Blagojevich was Patrick J. Fitzgerald, whom The New York Times describes as a close friend and colleague of Comey.

D'Souza, on the other hand, is a prominent figure on the right. The conservative website Daily Caller reported that it was Sen. Ted Cruz who was behind the push for Trump to pardon D'Souza. After Trump announced D'Souza's pardon, Cruz celebrated on Twitter, declaring that D'Souza is "a powerful voice for freedom, systematically dismantling the lies of the Left—which is why they hate him."

Though Trump said he doesn't know the right-wing figure, he called D'Souza personally to inform him of the pardon, the Times reported. D'Souza was prosecuted by Preet Bharara, a U.S. attorney who was fired by Trump (like Comey) and has been one of his fiercest critics on Twitter.

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All three of the prosecutors in the cases, Comey, Fitzgerald, and Bharara, have been at the receiving end of Trump's disdain.

According to CNN, his pardoning strategy raises the potential that it's intended to reassure former aides Special Counsel Robert Mueller is investigating that he has their backs, should they be convicted. "They can watch and hope and keep fighting ... this could be a message to Paul Manafort, this could be a message to Michael Cohen that, 'Hang in there and the cavalry will come sooner or later,'" CNN legal analyst Jeffrey Toobin said.

It's hard to predict what Trump's next move will be, or even what he might be thinking. But as far as a possible pardon for Stewart goes, the businesswoman — who has asserted that she was "unfairly targeted" in the investigation — most likely welcomed the news.