As Midterms Loom, Trump Finds Himself at a Crossroads on Multiple Fronts

November is shaping up to be a key month in Donald Trump’s post-presidential career, one in which he’s facing critical junctures on multiple fronts.

Obvious tests of Trump’s political strength will come from the midterm elections, where Trump-endorsed candidates are running across the country, and the prospect of Trump launching his all-but-announced presidential bid soon after. But November may also present pivotal moments in the investigations into the former President, mark a turning point in Trump’s use of social media, and reveal the durability of the election denial movement he helped spearhead.

The most immediate milestone will come on Tuesday, when Trump’s hand-picked candidates will be tested at the ballot box, and Republicans may end up with one or both chambers of Congress under their control. At a chilly rally in Sioux City, Iowa, on Thursday night, Trump described to his supporters how he views the midterm’s stakes. “There’s only one choice to end this madness,” Trump said. “If you want to stop destruction, save our country, and save the American dream, then this Tuesday you must vote Republican in a giant red wave.”

Just how big that wave will be could come down to several decisions made by Trump stretching back over a year. Old guard Republicans have been concerned that Trump endorsed flawed candidates in key swing states, crowding out primary challengers who were better suited for the general election. In Pennsylvania, TV personality Mehmet Oz is working to overcome accusations that he’s a carpetbagger from New Jersey. Hershel Walker in Georgia has grappled with allegations he paid for abortions and has repeatedly misrepresented his past on the campaign trail. J.D. Vance in Ohio has been dogged by perceptions that his views are too extreme for the state.

The outcome of those races will deliver a verdict on Trump’s political acumen for outpacing traditional Republican Party gatekeepers. If too many of his hand-picked candidates fall short, it could prompt party leaders to work more aggressively against him in the future.

“This is absolutely a test for Trump,” says Timothy Naftali, a presidential historian at New York University, one Naftali argues is tied up in the country’s feelings about the deadly attack on the Capitol on Jan. 6, 2021. “If Americans cast votes for Trump favorites in large numbers; then you have to conclude that at least for those Americans, the fact that Donald Trump at the very least inspired an insurrection doesn’t matter, or at least, doesn’t matter enough to have doubts about anybody that he favors.”

Once the results come in, Trump could find himself at another pivotal juncture, this one stemming from his continued efforts to undermine faith in the country’s elections. “We need a landslide so big that the radical left cannot rig it or steal it.” Trump told supporters at the rally in Iowa.

The former President’s repeated and unfounded election fraud allegations have seeped distrust into scores of races around the country, and encouraged many Republicans who deny Joe Biden won the 2020 presidential election to run for office this year. As votes are counted on Nov. 8 and in the days after, losing candidates in various states could refuse to concede their races, leaving Trump with a chance to stoke that frustration and spread more disinformation about the election system, or stay quiet.

Read more: Trump Rallies Iowans Ahead of Midterms Warped by His Election Lies

Beyond further eroding trust in the democratic process, Trump’s relentless focus on undermining faith in U.S. elections may have hurt the Republican Party’s midterm efforts, says Lauren Wright, a political scientist at Princeton University. “For Republicans to win they need moderate and independent voters. Those types of claims risk alienating moderate and independent voters.” While the latest polls suggest Republicans may have a good night on Tuesday, Wright argues that whatever the outcome, the GOP probably would have won even more seats if not for the party’s election denial position, raising questions of whether they could have done better.

Trump is holding a final swing of rallies in the days before Tuesday’s election. His decision to hold the first of those rallies in Iowa, which traditionally holds the first caucus of the presidential cycle, drew speculation that the event was meant prime the pump for Trump’s next presidential run. The former President has been teasing for weeks his intention to run for another term in 2024 and is reportedly poised to make an announcement later in November. “I ran twice, I won twice,” Trump told supporters at the rally in Iowa. “And now in order to make our country more successful and safe and glorious, I will very, very, very probably do it again.”

The announcement is highly anticipated by many of the former President’s supporters. At the rally, some wore “Trump 2024” paraphernalia. Justin Hefling, 36, from Yankton, South Dakota, said he wanted Trump to run again because he wanted “someone back in office who says shit how it is.”

Along with the political ramifications of Trump’s announcement, there will also be legal ones, as several investigations into his activities are continuing apace. Attorney General Merrick Garland is mulling whether a Trump candidacy would create the need for a special counsel to oversee ongoing federal investigations into the former president’s mishandling of hundreds of government documents and his efforts to overturn the 2020 election, according to a report this week from CNN.

A separate investigation into his business in New York City is moving forward and threatens to impair his ability to operate his family real estate company. And the Supreme Court ruled on Nov. 1 that a key Trump ally, Senator Lindsey Graham, couldn’t avoid testifying in a case in Georgia led by Fulton County District Attorney Fani Willis into Trump’s effort to press officials to change local results in the 2020 election.

Read more: How Trump Survived Decades of Legal Trouble

Speaking in Iowa, Trump framed the legal pressure on him as a way to silence him and his supporters. “They are coming after me because I’m fighting for you, remember that,” Trump said.

Trump took aim at New York Attorney General Letitia James during his speech, accusing her of leading a politically motivated investigation against him. Trump tried to put James’ efforts to hold the Trump Organization accountable for alleged tax violations and loan misrepresentations in the same category as seizures by socialist and Communist governments. The New York attorney general “started a process of property confiscation that is akin to Venezuela, Cuba, the old Soviet Union,” Trump told supporters Thursday night.

While major developments in the political and legal worlds would be enough to mark November as a pivotal month for Trump, events over the next several weeks may also have big implications for Trump’s social media presence. It’s been nearly two years since Twitter permanently suspended Trump in the aftermath of the Jan. 6 riot over concerns that Trump’s tweets to his 88 million followers risked “further incitement of violence.” Trump has since launched his own social media site, Truth Social, which some of his far-right supporters have embraced.

But last week Twitter got a new owner, Elon Musk, who has suggested that Trump’s suspension was a mistake. Musk has said he would create a “content moderation council with widely diverse viewpoints” to consider reinstating suspended accounts. If Musk reverses Trump’s suspension, Trump may be tempted to return to the platform and its reach.

In Iowa, Trump didn’t mention Musk or the prospects of his tweeting again. But he did find time to plug Truth Social, which remains his main social media platform for now.

“Go out and sign up for Truth Social,” Trump said. “It’s a hot site.”