Secrets, Sweetheart Deals, and Political Ambitions: The Byron Donalds Paradox
Gage Skidmore, CC BY 2.5 <https://creativecommons.org/licenses/by/2.5>, via Wikimedia Commons

Secrets, Sweetheart Deals, and Political Ambitions: The Byron Donalds Paradox

The former drug dealer is two steps from becoming Governor.

In 1997, when Byron Donalds was either 18 or 19, he was arrested for possession of marijuana. I’d tell you his exact age, but the date of his arrest is not in any public documents. He was offered a pre-trial diversion program, typically offered to first-time nonviolent offenders, especially young adults deemed worthy of a second chance. These programs usually involve:

  • Drug education or counseling
  • Community service
  • Probation-like supervision
  • Dismissal of charges upon completion

Donalds was charged with misdemeanor marijuana possession, which involves less than 20 grams. One would think the amount would be determined by weighing it, but there is no record of the amount Donalds was carrying. The name of the judge who dismissed his case in 2000 has not been made public. It is as if it never happened.

Usually, I wouldn’t be mad about a young Black man getting a break for possessing a small amount of weed. At the same time in my life, I dabbled with marijuana, but for the grace of God, it could have been me, and that’s the type of resolution I would have hoped for. But Donalds was more than someone indulging for personal use. According to his ex-wife, Bisa Hall, Donalds was a drug dealer, using sales to improve his finances. She had a lot to say about Donalds.

“He told me he was from Jamaica, and he had a Jamaican accent — and he was cute,” Hall said. “Then the next time I saw him, the Jamaican accent was gone, and he said he was from New York.

"We had so much fun together. At that time he was the greatest thing ever. He didn’t have anything to give me, his family wasn’t well off, but he was my first love. He was rough around the edges. There’s a polish there now that wasn’t there before. He would talk about how he grew up in a bad neighborhood and talk about how his family was poor. He had charm, but it was street charm. What he lacked was money.

"The shininess of your relationship kind of falls off after a while. You realize that person stinks sometimes and isn’t always awesome. You don’t like to pay all the bills. He was always complaining about how he didn’t have any money.

We had this neighbor who sold drugs, and they got close. Byron thought that was his path to fix his money situation. He was making bad choices. It never made sense to me why he did it. I had a level of concern. I had to worry, ‘What if he got arrested?’”

Perhaps the State of Florida did not know about Donalds drug dealing and acted appropriately based on the information they had. Florida should have at least been watchful, should the name of Byron Donalds come before them again in a criminal capacity. In 2020, the same year he was discharged from the pre-trial diversion program for marijuana possession, Donalds was arrested for bribery and bank fraud involving a fraudulent check and debit card transaction. Rather than face trial, Donalds entered a pre-trial diversion program, which allowed him to avoid a formal conviction. The charge was later expunged, meaning it was legally erased from public records.

Donalds twice got sweetheart deals that kept him out of jail and left him without a criminal record. After becoming a politician and serving on multiple boards of directors, an ethics complaint was lodged in 2020 alleging that Donalds had “falsely and criminally completed regulatory applications” by omitting both the bribery charge and his earlier marijuana arrest. Donalds claimed that because the bribery charge was expunged, he had no obligation to report it. He said the marijuana arrest was “almost the same thing” because he completed a pre-trial diversion program.

Once a Congressman, Donalds exuded a tough-on-crime persona, wanting to eliminate programs like the ones that benefited him, closing the door behind himself. In 2024 and 2025, Donalds introduced the DC Crimes Act, specifically seeking to:

  • Cap eligibility for youth rehabilitation programs at age 18
  • Prevent individuals aged 18–24 from receiving flexible sentencing or having their records sealed under D.C.’s Youth Rehabilitation Act

Rep. Jasmine Crockett (D-TX) called Donalds out on his hypocrisy:

“As I sat and listened to the beginning of this debate, my heart simply broke," said Crockett. "And many people know me for being able to do alliterations, and all I could think about was ‘amnesia allows adolescent accountability avoidance, agility from across the aisle.’

"Work with me for a second: Imagine being a young man born to Jamaican and Panamanian parents who messed up not once but twice. Imagine standing in front of a judge with your life hanging in balance, and instead of prison you’re given a promise of mercy. Your record is wiped clean, and you’ve got a second chance at life. Imagine turning that into a promotion and you go to college and get a job and even become a member of Congress. That’s what redemption looks like.

That’s what America is supposed to be about. And that is exactly the story of the next wannabe governor from Florida, as a young man, he went through. He was given a third chance, and now he’s the face of a bill that would not afford young people in Washington, D.C. the same opportunities afforded to him."

Byron Donalds has announced he’s running for the office of Governor of Florida and has the full-throated support of Donald Trump, a convicted felon himself.

Byron Donalds would be a truly Great and Powerful Governor for Florida and, should he decide to run, will have my Complete and Total Endorsement,” said Trump. “RUN, BYRON, RUN!”

Florida isn’t typically known for its leniency, but even before letting Jeffrey Epstein return to his predatory ways after a 2004 arrest, Florida put a drug dealer and a fraud back on the streets, and we weren’t allowed to know.

So now, as Donalds stands two steps from the governor’s mansion, the Republican nomination and general election, we’re told to forget what we were never allowed to know. We’re told to admire his rise, not question the scaffolding beneath it. We’re told — by Donald Trump, by the Florida GOP, by the same lawmakers who push mandatory minimums and criminalize poverty — that Donalds is a model of redemption. But redemption without accountability is just privilege in disguise. And when the man who twice escaped justice now seeks to deny that same mercy to others, it’s not leadership — it’s betrayal. Florida didn’t just give Donalds a second chance. It gave him a clean slate, a sealed record, and a platform built on silence. Whether he becomes governor will be up to the people, who have a right to be informed.

This post originally appeared on Medium and is edited and republished with author's permission. Read more of William Spivey's work on Medium. And if you dig his words, buy the man a coffee.