One of the first things Milton McGregor ever told me was that he wouldn’t lie to me.
That was in March 2014, several months before I wrote an in-depth series on the history of gambling in Alabama and McGregor’s role in it. It was the first of many interviews, and McGregor wanted to set the ground rules.
“Let me set some things straight so we understand each other,” McGregor said. “If I tell you something is a fact, by God, you can take it to the bank. I won’t ever lie to you. I might tell you I don’t know for sure something is true, or that I believe something to be true but can’t confirm it, but I won’t ever lie to you.”
It was a promise he didn’t keep.
It would have been tough for anyone to do so. After all, that initial interview lasted three hours. A few days later, there was another that lasted two hours.
Over the next four years, I literally can’t tell you how many times I spoke to Milton McGregor — about gambling, about politics, about our families, about business, about sports and just about life.
Oh, I’m not foolish enough to believe that a then-75-year-old billionaire met me and became mesmerized by my sensational intelligence and wit, and wanted to bounce ideas off of me. McGregor found in me what he had wanted for a long time: an open mind and limitless ink.
He had been wronged by Bob Riley and the U.S. government, and he wanted to tell his story. Not in pieces and soundbites, as it had been reported before, but in totality.
When that full story was published, he told me once, he felt vindicated. He felt like there was finally a recorded history of all the ways he was wronged. That finally, someone had taken the time to put it all together.
Honestly, I hadn’t done McGregor any personal favors. I just went back through old newspaper stories and interviewed about a hundred people and told the story of gambling. That it was favorable to McGregor in print only occurred because the facts in real life were favorable to him.
The man had been screwed.
It’s really that simple, and it was impossible to sugarcoat.
But that reality was a minor point to McGregor. From that day forward, I became someone McGregor believed he could trust. Or as he put it, I was a person who “has the balls to report the truth.”
And so, the phone calls and meetings began.
Often, I had no clear understanding of why I was meeting with McGregor. He would call, say “hey, big man, I need about 20 minutes of your time” — which really meant two hours — and I’d meet him at his office. Inevitably, I would leave with a manilla envelope, prepared by his secretary, Linda Pittman, and containing some piece of information that McGregor wanted me to read through and learn more about.
He quite literally gave me homework.
But I didn’t care. McGregor was bribing me with the only currency I cared about.
At least half of the time we spent together was devoted to him recounting 40-plus years of Alabama political stories. And not the stuff you read in the newspapers — the real dirt. The stunts he pulled. The stunts others pulled. The payoffs and paybacks and secret blackmails. The sex scandals and secret lovers.
McGregor was basically an oral history of Alabama’s smoke-filled back rooms.
I learned more about the inner workings of Alabama politics in an hour of talking to McGregor than I could learn in a lifetime of roaming the State House halls.
Somewhere in the midst of all those talks, I think it’s safe to say that we became friends. And I saw a side of McGregor that most never did.
I could tell you stories about his generosity that would blow your mind. About the hospital bills he paid for his former employees after they lost their jobs and health care when the casino was raided. About the numerous times he used his plane to fly people who were in desperate situations. About the millions of dollars he’s given away to help people and the community over the years.
But McGregor wouldn’t want that. He’d much rather I remind you that Bob Riley should, in Milton’s words, “be under the damn jail.” And he’d probably follow that pronouncement up with a colorful saying, something along the lines of: “I wouldn’t trust Riley in a s**thouse with a muzzle on.”
Then he would apologize, because he’d promised Pat that he was going to cut down on the cussing.
And without fail, at the end of every phone call or meeting — no matter the topic of conversation or what he had going on — he would ask about my family. Over the last few months, as my wife and I prepared for the arrival of our daughter earlier this month, McGregor called countless times just to check on us.
Last week, I met with McGregor at his house for a bit. As I was leaving, he asked about the baby and said he wanted to get together for dinner and meet her.
“We’ll do that. Sometime in the next two weeks, I’m going to meet her,” he said.
To my knowledge, it’s the only time Milton McGregor ever lied to me.