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Jeff Sessions’s Never-Ending Pursuit of Donald Trump’s Affection

After a disastrous stint as attorney general, Sessions is trying to win back his old Alabama Senate seat—and regain the president’s favor in the process

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On Thursday, Jeff Sessions aired the first advertisement for his 2020 Alabama Senate campaign. It’s a perilous run for Donald Trump’s former attorney general, and it’s happening under exceptional circumstances. Sessions didn’t launch his campaign with proud pronouncements citing his record as a four-term senator in Alabama, nor did he point to his time in Trump’s Cabinet, even though the president enjoys some of his highest approval ratings in the state. No, Sessions announced his campaign with defensive reassurances about his loyalty to his former boss, who remains supremely dissatisfied with him.

In the video, Sessions stands before a bare wall, facing a crappy webcam, to address his once (and maybe future) constituents with a distressed smile. “When I left President Trump’s Cabinet, did I write a tell-all book? No. Did I go on CNN and attack the president? Nope. Have I said a cross word about our president? Not one time,” Sessions says. Indeed, his advertisement, titled “Great Job,” appears to be an act of desperation addressed exclusively to Trump. “The president is doing a great job for America and Alabama, and he has my strong support,” Sessions concludes.

Sessions’s endorsement of the president is unlikely to be reciprocated. Voting in Alabama’s Senate Republican primary takes place in March, and Trump reportedly refuses to endorse Sessions. His disapproval of Sessions stems from his belief that as his attorney general, Sessions did not do enough to protect him from special counsel Robert Mueller’s investigation into Russian interference in the 2016 election. Sessions became a frequent target of the president’s derision: Trump described Sessions’s performance as “very weak,” “beleaguered,” and “disgraceful” during his tenure at the Justice Department. “I don’t have an attorney general,” Trump told The Hill two months before Sessions resigned in November 2018. As recently as last week, Trump ridiculed Sessions as a “jerk,” according to The New York Times. Sessions has spent the past year in the post-Trump wilderness. He hopes to reemerge in familiar territory in the Senate, but his reinvention is complicated by the fact that the president seems to loathe him more vividly than any other Republican. Sessions may not aspire toward “Never Trump” camaraderie, but he’s earned the proportionate disdain.

It’s been a long fall from Trump’s grace for Sessions since he leveraged his endorsement of Trump’s presidential campaign in February 2016—the first by a Senate Republican—to an appointment as Trump’s first attorney general. Part of Sessions’s appeal to Trump, aside from his eagerness to champion his candidacy, was his steadfast commitment to hardline immigration restrictions, many of which Trump has pursued. As a candidate, Trump credited Sessions as his chief congressional ally: “He’s really the expert,” Trump said, “on borders, on so many things.”

Sessions’s former Senate communications director, Stephen Miller, now leads immigration policy in Trump’s White House, and his former Justice Department chief of staff, Matthew Whitaker, briefly succeeded Sessions as the acting U.S. attorney general. Sessions’s influence, then, endures in Trump’s White House, even as he faltered worse than any of Trump’s former flunkies in remaining in the president’s good standing. Sessions’s political career lives and dies by Trumpism. “If I do this endorsement and it doesn’t work,” Sessions told Bannon in February 2016, “it’s the end of my career in the Republican Party.” The endorsement “worked” in getting Sessions a short-lived promotion, but it’s proved ruinous to his long-term career prospects.

Unsurprisingly, Trump and Vice President Mike Pence have declined to endorse or encourage Sessions in his Senate campaign. “Mr. Trump sent word to Mr. Sessions through allies that he would publicly attack him if he ran,” The New York Times reported last week. Senate Majority Leader Mitch McConnell privately worries about a prospective primary between Sessions and former Alabama judge Roy Moore, who narrowly lost in a special election for Sessions’s vacated seat in 2017 to Democrat Doug Jones. During the campaign, several women reported Moore sexually assaulted them as teenagers, which Moore has denied. The party’s concerns aren’t limited to the optics of a messy, competitive primary. On Wednesday, Florida Representative Matt Gaetz, a Republican, tweeted “Jeff Sessions returning to the Senate is a terrible idea.”

Sessions may not have much difficulty beating a disgraced opponent like Moore in the primary, but he continues to struggle to prove his “loyalty” and his usefulness to a president who betrays even his most crucial and uncritical allies on a whim. The Trump White House hosts many unsteady accomplices arguing the case against Trump’s reelection in 2020, including the anonymous staffer who will soon publish a book, A Warning. Trump churns out disgruntled figures, such as former secretary of state Rex Tillerson and former defense secretary Jim Mattis, who both disparage Trump as private citizens as freely (if not as effectively) as Trump disparages them. There are also the loyalists, such as South Carolina Senator Lindsey Graham and former U.N. ambassador Nikki Haley, who both previously opposed Trump but now wish to remain on the president’s good side. The loyalists don’t seem to respect Trump so much as they fear him; they’ve watched Trump eviscerate Bannon and Sessions, two men who pioneered Trumpism only for Trump to dropkick them from his confidence. Bannon now hosts a radio show, War Room: Impeachment, designed to “advise” Trump from afar. Sessions, meanwhile, hopes to bolster Trump’s agenda from a safe but nonetheless powerful distance in the Senate. To do so, he’ll require Trump’s acquiescence, if not his endorsement, in order to overcome Jones.

Sessions should be a cautionary tale for Republicans who flatter Trump, a man who, ultimately, betrays everyone. Instead, he’s become a cautionary tale for Republicans who might cross Trump in even the most clueless and indirect fashion. He isn’t some dissident Republican like Mitt Romney or Jeff Flake. Sessions didn’t oppose, criticize, or question Trump at the Justice Department. He simply recused himself from oversight of Mueller’s investigation. But Sessions defied Trump’s theory of governance, which doesn’t serve U.S. citizens, or even conservatism, as obsessively as it serves Trump. “Sessions should have never recused himself, and if he was going to recuse himself, he should have told me before he took the job, and I would have picked somebody else,” Trump told The New York Times two years ago. It’s strange to see Sessions become more troublesome to the president than all the “Never Trumpers,” and their book contracts. Of course, Sessions’s successors, Whitaker and current AG Bill Barr, have proved far more cooperative in Trump’s efforts to ignore Congress and the courts.

Sessions has reemerged in a calamitous political landscape for Trump loyalists. Last week, Kentucky Governor Matt Bevin, a Republican, appears to have lost his reelection campaign despite Trump’s vigorous endorsement, which culminated in a MAGA rally in Lexington, Kentucky, on Monday evening. “If you lose,” Trump warned Bevin, “they are going to say Trump suffered the greatest defeat in the history of the world.” Last week, Virginia Democrats won control of the state Senate and now dominate the state government. Trumpism lost on multiple fronts, but Bevin’s apparent loss stands out. He’s a staunch Trump ally and a Trumpian governor, and his opponent, Democrat Andy Beshear, ran as a conventional Southern Democrat in a state where Trump bested Hillary Clinton by 30 percentage points in the 2016 presidential election. Assuming he wins the Republican primary, Sessions will challenge Jones in a year when most Democratic presidential primary candidates are projected to defeat Trump in the national popular vote. In Alabama, however, Sessions faces a curious challenge: Trump is so popular in the state—second only to the Republican governor Kay Ivey in statewide popularity—and the president is so vindictive in his opposition to Sessions that he may well turn Republicans against Sessions.

Sessions might not be the only Trump White House alumnus to seek statewide election. In June, White House press secretary Sarah Sanders resigned from the Trump administration under far less acrimonious circumstances. Trump has urged Sanders to run for governor in Arkansas (where Sanders’s father, Mike Huckabee, served as governor for more than a decade). Sanders hasn’t confirmed her intentions, and she’s no sure bet to win her party’s nomination in the gubernatorial race; 40 percent of Arkansas voters polled in July 2019 regard a Sanders run as “a bad idea.” Sessions polls better in Alabama than Sanders does in Arkansas, but he joins Bannon, former press secretary Sean Spicer, and former national security adviser John Bolton in decorated disgrace: Ultimately, these figures disgusted Trump, but they nonetheless represent his agenda with distinct (and perverse) credibility. Sessions may struggle to win Trump’s endorsement, but he will not struggle to prove his contributions to Trump’s political project.

Granted, Trump’s political project is, in large part, a cult of personality. Gaetz has no self-authored reasons to oppose Sessions’s return to the Senate; he’s just repeating the edicts. If Trump says Sessions is out, then Sessions is out. There’s hope for Moore yet. But Bevin’s apparent loss in Kentucky once again reveals the peril of appealing so exclusively to reactionaries who worship one man. If even Jeff Sessions is too treacherous to please Trump, then who can be trusted to carry the mantle of Trumpism in November 2020?