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The Diary of a Wimpy Kid: Jerry “Wimpy” Halstead won 85 fights but lost to the world’s best heavyweights

Thomas Gerbasi tracks down Jerry Halstead, a man served up for rising heavyweights of the 80s and 90s before retirement threatened to swallow him whole

BORN, raised and still living in Oklahoma, Jerry “Wimpy” Halstead doesn’t scare easy. So don’t ask him how he deals with the reality of life-threatening weather in his home state.

“Those tornadoes aren’t nothing, man,” he chuckles. “I’ve lived with them all my life. It’s all pretty normal stuff around here.”

That fearlessness could be a testament to having competed in over a hundred professional boxing matches, or maybe it’s because he’s lived through worse experiences than whatever some wind and rain can bring him. Whatever it is, the 56-year-old Halstead is a survivor. He knows it and he’s thankful for it.

“I have people that are amazed,” he said. “I’ve weathered the fight game very well, considering the level where I was at, and I still do what I do. I can’t say it enough how blessed I feel about having those abilities and that cognitive thinking ability. The type of work that I do is very dangerous and you can get hurt easily, but I’ve been doing it so long, and being ambidextrous comes in real handy in the type of trade that I have.”

His days in the ring done for over two decades, Halstead now works in a business that was in his blood long before he put the gloves on, and as a commercial overhead doorman, he’s found a place where he’s content and able to live a comfortable life, a mix few of his peers get to experience once their fighting days are over.

“I was in the industry before I got fully locked in to being a contender and traveling and fighting,” he said. “My father was in the industry, so it was natural for me to be right back in it when I was done. I just picked up where I left off in a way and I’ve made a very good living. It’s not [Jeff] Bezos’ money [laughs], but who has that kind of money anyway?”

The younger members of Halstead’s crew know what he used to do for a living, even if he doesn’t tell them that the Michael Tyson that he knocked out in the fifth round in March of 1987 wasn’t THE Mike Tyson. And if he didn’t let that information slip, a look at him on the job makes it evident that he once was an athlete.

“They see me in the field and they’re amazed at some of the reaction time I have,” Halstead said. “But as far as boxing goes, I don’t throw my weight around like that. I’ve never been the bullying type. I could be boastful in some cases, and arrogant in others, depending on who it was and where it was and what was going on.”

Comments like that are a reminder that even as he approaches the age of 60, Halstead still has fighting in his blood, and that will never change. Subsequently, he admits that he misses it at times.

“It’s hard not to miss some of it,” he said. “It’s such an involving aspect of your life for so long that you develop traits and a way of living your life and doing things. You get to where you miss the fans, you miss the noise, and then there’s the blood and the sweat and all that too. I miss those things sometimes.”

Jerry Halstead, the man who fought them all

Not surprising, especially considering that Halstead competed as a pro from June of 1980 until December of 1997, a more than 17-year run that saw him compile a 85-19-1, 1 NC record with 63 wins by knockout scored over five weight classes from middleweight to heavyweight.

It was at heavyweight that most boxing fans knew the Oklahoman, a stablemate of former lightweight champion Sean O’Grady under the tutelage of O’Grady’s father Pat. It was in Oklahoma City that Halstead made his name fighting a wide variety of journeymen, opponents and no hopers, even if he wasn’t ready for prime time himself. But as the elder O’Grady told him, “There’s no money in being an amateur.”

Apparently, there was no money in being anything but a heavyweight, either, which meant the six-foot-one Halstead was going to be fighting an uphill battle every time he stepped into the ring with a naturally bigger foe.

“Pat O’Grady was adamant about the difference between the lighter weights and the heavyweights,” said Halstead. “The money wasn’t there in the cruisers, so from a financial standpoint, which was really all his game was – at least with me anyway – I had to go to heavyweight.”

Moving to heavyweight in 1985, Halstead won 15 straight with 13 knockouts over the usual suspects, his best win being a decision victory over Larry Frazier, before he was matched up with former world champ Greg Page in November of 1986. Page knocked Halstead out in eight rounds. Thus began a pattern. At home, Halstead was seemingly unbeatable. But when the competition ramped up, he lost. Tony Tubbs and Buster Douglas were two more former or future champions to beat him, but as he piled up wins in between, he would always get another shot.

In 1986, he even scored a guest appearance on the “Late Night with David Letterman” show, and six years later, there would be a quartet of big fights against Tommy Morrison, Ray Mercer, Alex Stewart and Herbie Hide, owners of a combined 99-6 record. Those fights went as expected, Halstead losing by knockout, with the highlight perhaps being when Wimpy was asked by referee Toby Gibson after a Morrison knockdown, “Are you all right?” The answer from Halstead: “Barely.”

Yet while his nickname, quick wit and devil may care attitude made many dismiss Halstead as a threat in the ring, he took his job seriously, even as bad business deals and personal issues began to take their toll.

“It was all preparation,” he said when asked what kept him from winning the big fights. “There were things behind the scenes in my personal life that were going on and there were some difficulties that kept me from getting on top of my game the way I needed to. That all goes back to the handlers and the people that have invested in you as a fighter and as a product. They literally did not focus me and re-direct me.

“I had to figure it out on my own and it took longer because of that and my performance suffered. The ownership in this whole deal is me because I’m the dude, I’m the one doing the work. But when you put trust and loyalty in people that have started your career and nurtured you early on and then you start to break out, you trust them and you count on them and then they don’t do the things they should have done. When you don’t have that, it can take the steam out of anybody’s sails.”

By the mid-90s, Halstead knew he was nearing the end. The business had exhausted him, and the idea of making any type of run at a title was equally spent. He still needed to make money, though, so he accepted a December 1997 bout against 17-1-1 German Willi Fischer. It’s a bout that doesn’t show up on Halstead’s record because it never happened. Instead, promoters told Halstead that Fischer was unavailable and that the only opponent that was able to step in was a 13-0 prospect fresh from winning an Olympic gold medal.

“I didn’t even know who Wladimir Klitschko was because he had just come out of the Olympics,” laughs Halstead, who points to this situation as a prime of example of where he was on the business side of the sport. “This is where the handlers come into play. It’s almost as if they were part of my undoing.”

Halstead still agreed to the fight, but as soon as he got in the same room as Klitschko, he knew what was coming.

“I was done,” he said. “I knew I was done when I saw Wladimir Klitschko. Simply because of my age, the condition that I had been in, the wars I had already fought, as well as the prep time. And when I said, ‘Hey, I’m done,’ I meant it. And I walked away from it and I don’t regret it. At that point, I realized it was time to move on to other passions.”

Klitschko needed only two rounds to put an end to the fight and Halstead’s career, and the American never came back. He wasn’t done fighting yet, though, and this battle was worse than any he faced in the ring.

“Drugs and alcohol got a hold of me really bad and I had a terrible time from 2002 to 2013,” said Halstead, whose terrible times included a vehicular manslaughter charge after an alcohol-related accident that killed his wife and a three-and-a-half-year prison sentence for driving while intoxicated. When he cleaned up and faced the outside world again, it was boxing that saved him, but not in the way you might think.

“It was just an unbelievable upheaval in my life, and I used all the training and discipline and focus that I had to get through my career at the level I did to help me through that dark period that I was in for many years,” Halstead said.

“I still have moments where those things still haunt me, but they’re very easily managed with the right tools. I’ve talked with some professionals, and I think if somebody has a problem making adjustments after boxing, talk to the professionals that can help them find something that works for them and makes them happy.

“When people aren’t happy, they walk around doing things they probably shouldn’t do. You’ve got to work real hard to keep that happy going because there’s a lot of things in this world that can take it away from you. So you’ve got to keep things in perspective.”

Halstead now has that perspective, both on life and his boxing career. I ask him if things would have been different had he been allowed to compete as a cruiserweight, where he wouldn’t have been in with monsters every night once he hit a certain level.

“It would have a lot different outcome in a lot of different areas,” he admits. “I do believe, with retrospect and knowing how things work, in not just the business world but on the athletic end of things, the O’Gradys were fine early on in my career, but there came a point where if I had been handled differently, I would have had a different course.

“But I battled that demon a long time ago with the woulda, coulda shouldas. I can’t undo what’s been done, I’ve just gotta learn from it and go on living with it. I do know there’s some guys out there who are probably glad I didn’t stick around in the cruiserweight division.”

Halstead laughs, and he sounds like a man at peace. I tell him of his fighter profile on the CyberBoxingZone.com website, where he is described as “A durable battler who came to scrap.” Is he satisfied with that being his fistic legacy?

“I would think that was very accurate,” he said. “Anybody who signed to fight me, maybe they took me seriously, maybe they didn’t because they heard the nickname ‘Wimpy.’ But in the ring, all that changed; it was business and it was time to show ‘em what you got. If you’re gonna show up, you need to show off and show out, as much as you possibly can. And if you saw me fight, I didn’t come there to play.”

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