Election Day is just three weeks away, and Donald Trump is not in prison.

That’s an obvious fact. Yet it wasn’t too long ago that some people thought the former president might have to campaign from the clink.

The political left was banking on a quartet of criminal cases to sink Mr. Trump, even if the White House and Democratic lawmakers tried to distance themselves from the formal gears of justice. And prosecutors who secured headline-grabbing indictments wanted to begin picking juries in the middle of the 2024 presidential campaigns.

Instead, Mr. Trump is a free man in a neck-and-neck race against Vice President Kamala Harris.

It’s a remarkable turn of events for Mr. Trump, who, through skill and luck, quashed one federal case, watered down another and stiff-armed a trial in Georgia by raising questions about the prosecutor’s romantic life compromising the case.

Sentencing in the one case that caught up with him, a hush money conviction in New York, won’t occur until after Election Day.

Far from drowning in a sea of charges, Mr. Trump is statistically tied to Ms. Harris in swing states and had his biggest scare when a bullet grazed his ear in Butler, Pennsylvania — not in a courtroom.

It’s not how Democrats envisioned things would unfold a year ago when they gloated over Mr. Trump’s mugshot in Atlanta.

“We got you! And more to come — clown, thug, crook, criminal,” Rep. Jamaal Bowman, New York Democrat and member of Congress’ liberal “Squad,” said in an online video that featured Mr. Trump’s picture and the congressman laughing hysterically.

A little over a year later, it was Mr. Bowman who went down in defeat in the Democratic primary.

At the start of 2024, many people thought Mr. Trump would be “under a mountain of legal problems and multiple trials and forgot about the fact that, in many cases, it’s pretty easy to move a case,” said David Schultz, a professor of politics and legal studies at Hamline University who is tracking Mr. Trump’s legal issues.

He said it is common for charges to get dropped or for new legal issues, evidence and witnesses to emerge. Plus, the cases against Mr. Trump are complicated.

”It’s not a breaking-and-entering case,” Mr. Schultz said. “These are really complex cases with a lot of complex litigation. I think there was a bit of an exaggerated sense of what was going to happen and how quickly.”

One of Mr. Trump’s biggest breaks came from a midsummer Supreme Court ruling that presidents are immune from prosecution for “official acts.”

The decision delayed a case brought by Justice Department special counsel Jack Smith alleging Mr. Trump conspired against the U.S. and its voters following the 2020 election. It also forced Mr. Smith to revise the indictment.

The ruling also raised questions about Mr. Trump’s conviction in New York. While the trial judge is expected to move ahead with sentencing, appeals courts are taking a second look at White House-related evidence that Manhattan prosecutors used to secure a guilty verdict in May.

Mr. Trump got another boost when U.S. District Judge Aileen Cannon, another of his appointees, dismissed a case that alleged the ex-president took classified records to his Mar-a-Lago estate.

The judge said Mr. Smith was a private citizen when Attorney General Merrick Garland plucked him to pursue cases against Mr. Trump. That violates the Constitution’s Appointments Clause, the judge ruled.

Mr. Smith is appealing the decision. For now, Mr. Trump’s critics say he is benefitting from his picks to the federal bench.

“When you load the dice, you can be certain that you will not roll snake eyes,” said Ross Baker, a politics professor at Rutgers University in New Jersey.

Yet Mr. Trump’s big break in Georgia is the product of high-level sleuthing by a lawyer for one of his co-defendants.

Ashleigh Merchant, an attorney for Trump ally Michael Roman, dropped a bombshell by moving to disqualify Fulton County District Attorney Fani Willis over a romantic relationship she had with a lead investigator on the case.

The judge declined to disqualify Ms. Willis as long as the former boyfriend, Nathan Wade, resigned from the case. Defense attorneys are appealing that decision, however, a process that pushed the case beyond the election.

Mr. Trump’s campaign said his opponents are the victim of their overreach.

“The Comrade Kamala Harris-Crooked Joe Biden Witch Hunts against President Trump have imploded just like their failed campaign, and should all be dismissed in light of the Supreme Court’s historic decision on immunity and other vital jurisprudence,” Trump campaign spokesman Steven Cheung said. “The lies of the liberal lawfare pursuit of President Trump have blown up spectacularly.”

The Washington Times reached out to the Harris campaign for comment on Mr. Trump’s legal situation but did not hear back.

Mr. Trump did not escape his year of legal turmoil unscathed. He is running as a felon after his conviction on 34 counts of falsifying business records in New York.

Democrats dropped their pretenses and highlighted Mr. Trump’s status as a “convicted felon” in campaign ads. The verdict even sparked speculation about whether Mr. Trump would have to campaign from jail.

Some people looked to historical comparisons, such as Eugene V. Debs, who ran from prison on the Socialist Party ticket in 1920 after speaking out against American involvement in World War I — a violation of the Sedition Act.

However, Mr. Trump’s delay tactics worked again, with state Supreme Court Justice Juan Merchan agreeing to postpone Mr. Trump’s sentencing to review the Supreme Court’s immunity decision and avoid any appearance of bias before the election.

Mr. Trump could do time behind bars after his Nov. 26 sentencing, though as a 78-year-old first-time offender, he’s just as likely to catch another break.

“The odds of him actually seeing jail time on that,” Mr. Schultz said, “were incredibly low to start with.”