The Darkness and the Light: Wimpy Halstead

By Robert Mladinich on October 24, 2016
The Darkness and the Light: Wimpy Halstead
Halstead said he took one look at the giant Ukrainian and told himself, “I’m done.”

He is as articulate as he is unabashed and audacious, and he is the first to admit he has quite a story to tell…

Fighting professionally from 1980 to 1997, Jerry “Wimpy” Halstead compiled an enviable record of 84-19-1 (62 KOs).

He traveled the world, fighting such championship caliber opponents and top contenders as Greg Page, Tony Tubbs, James “Buster” Douglas, Tommy Morrison, Pierre Coetzer, Ray Mercer, Alex Stewart, Herbie Hide, Brian Nielsen, Jeremy Williams and Wladimir Klitschko.

He more than held his own against several of those top-tier opponents. In speaking with him today, it is hard to fathom he fought as much and as often as he did. He is as articulate as he is unabashed and audacious, and he is the first to admit he has quite a story to tell.

His saga begins in Midwest City, Oklahoma, a suburb of Oklahoma City, the state capital. Raised in a two-parent home, Halstead was the middle child in a family of three boys. His father was a roofer, his mother a beautician. They met and married as teenagers and had children right from the get-go. 

Halstead had a somewhat complicated and troubled relationship with his father, so he acted out in more ways than he cares to remember as a youngster. 

He threw paintballs at passersby and vehicles, stayed out past a family and municipal curfew, and got into fights with grown men when he was barely a teenager.
At the age of 16, things took a turn for the worse when he was arrested for felonious assault. His hometown football team was playing its arch-rival Dell City, and Halstead threw an egg at a boy from the other school.

When the victim of the egging smashed a bottle to retaliate, Halstead grabbed a piece of wood that he said was more like a “makeshift billy club.”

The two went at it and Halstead came within inches of causing what he describes as “very serious damage” to his nemesis. He was arrested for assault and battery with a dangerous weapon and spent the weekend in jail.

A tough but benevolent female judge saw some redeeming quality in Halstead. Even after looking at his lengthy record of teenage hijinks, she gave him the choice of going to reform school in Boley, Oklahoma, or coming up with a more constructive way of handling his destructive tendencies. 

She told him in no uncertain terms that if he appeared again in her courtroom, he would be escorted out in handcuffs with no questions asked or answered. 

Before long, Halstead, who loved fighting but had no inclination toward boxing, found his way to Pat O’Grady’s gym in Oklahoma City. O’Grady, a colorful rogue, was grooming his son Sean, a sterling professional lightweight, for superstardom by having him fight locally several times a month.

Pat also handled a rough 6’4” heavyweight named Monte Masters who would marry his daughter Rosie O’Grady, lightweight Frank “Rootin’ Tootin Newton, and super lightweight Pat Duran.

Halstead, who started training as a gangly middleweight, experienced daunting challenges in the beginning. On a regular basis, the behemoth Masters, who was eight years Halstead’s senior, beat him mercilessly.

Pat O’Grady rarely, if ever, rang the bell early or told his future son-in-law to ease up on the neophyte. 

“Pat was a former Marine, very old school and there was a lot of hardness about him,” said Halstead. “But he was adamant about conditioning, and always said conditioning made the difference between winning and losing.”

If nothing else, Halstead could physically withstand the punishment, so Pat used him as a regular sparring partner for Masters.

There were many times when Halstead wanted to quit, but the thought of going back to the streets or to jail scared him more than the frightful beatings he took on a daily basis.

“Boxing reigned me in and directed my energy from being undisciplined and getting into trouble all the time,” said Halstead. “Something inside me told me that quitting was not a good way to go. When you quit at something — whatever it is — you lose a little piece of yourself.”

Making things worse was the fact that Newton took to calling him “Wimpy.” Before long, Masters and Sean O’Grady were calling him the same name — and even added other derogatory monikers to their repertoire. Some of the names might even make Donald Trump blush.

Halstead eventually proved that he was no wimp, and within four or five months he was holding his own against Masters despite a 50-pound weight disadvantage. A little more than a year into training, he had a startling revelation.

“I realized I could be successful at boxing, at more than just a mediocre level,” explained Halstead. “If I kept at it, I could make some noise. 

“I had speed on my side,” he continued. “It got to where I could hang with Monte, but we had some rough sessions. We would sometimes throw elbows and knees and even spit at each other.”

After an especially vicious sparring session with Masters, Halstead was shocked at the reaction from Sean O’Grady, who was by then a world-ranked contender about a year and a half away from beating Hilmer Kenty for the WBA lightweight title in April 1981. 

“Sean called me a wimp, said I’ll never be anything but a wimp, and why don’t I just walk out and not come back,” recalled Halstead.

The two began scuffling, but the fracas was quickly broken up by Pat, who promptly barred Halstead from the facility.

Once away from the gym, Halstead realized how much he missed it. It was only after Halstead’s father spoke with Pat that he was allowed back. 

By then Halstead was a senior in high school and eager to begin an amateur career, but Pat urged him to fight professionally on Sean’s undercards where he would, in effect, learn on the job while getting paid for it.

Halstead turned professional in June 1980, the same month he was scheduled to graduate from high school. When he came up several credits short for his commencement proceedings, Halstead enthusiastically embarked full-time on his boxing career, often fighting several times a month in and around Oklahoma City.

“It was rare for me to quit anything, so not finishing high school always bothered me,” said Halstead. “I lost a piece of my pride, but I was also getting a lot of positive attention from my boxing fans. The local media was very supportive.”

Pat O’Grady took to calling his formidable stable “The Five Eagles.” 

After racking up 22 straight victories, Halstead lost a split decision to undefeated Mike Costello in Connecticut. Halstead had wound up on the East Coast after first following Pat and Sean to California, where despite having a 10-year, 50-50 contract with Pat, Halstead was told by Pat he would have to get a full-time job to augment his ring earnings.

Halstead got disenchanted with the O’Gradys and moved back to Oklahoma, when a businessman from Connecticut offered him a deal despite the fact that Halstead was still contractually bound to Pat. 

Halstead said he didn’t believe the O’Grady contract could be enforced because he thought it was illegal, but admits that, “I didn’t realize the power of the people Pat knew.”

“There was no way I lost to Costello,” said Halstead, suggesting that Pat somehow played a role in him getting the short end of a split decision.

Halstead fought Costello again four months later in Atlantic City, but was stopped in the second round.

“At that time I was living with two women and acting crazy,” said Halstead. “That fight brought me back to earth.”

A few bouts later, Halstead battled the hard-punching Alvino Manson, hoping a victory would launch him into the ratings. He was training in Camden, New Jersey, and said he was ahead on points, but remembers nothing after the third round. Once again Halstead suspects some underhanded tactics by his corner. 

With his life spiraling out of control, Halstead went back to Oklahoma, where Pat and Sean had once again relocated. It took Halstead nine months to be accepted back into O’Grady’s gym, but Pat told him he was going to have to compete as a heavyweight.

Halstead’s first bout at that weight was against unheralded Fred Muhammad in Wyoming in September 1985.

Within two years, Halstead was battling the likes of former belt holders Greg Page and Tony Tubbs in Las Vegas. He was still fighting locally, but had been signed to a three-fight contract with Don King, the first two of which were against Page and Tubbs. 

Halstead said that Pat O’Grady was “big on hyperbole” but it was Halstead’s own oversized personality that got him booked on the “David Letterman Show” in New York in 1986.

“David was still relatively new to late night,” said Halstead. “The New York press said I would make Joan Rivers look like a wallflower. Pat always said any press is better than no press.”

By the late 1980s, Halstead was winning fights at or near home, but losing against better known prospects on the road. He was competive but ultimately stopped by Buster Douglas in 1988, which culminated his relationship with Don King.

Halstead soon got back on the winning track, albeit against limited opposition. Three years later, in July 1991, he fought top-ranked Pierre Coetzer in his home country of South Africa.

Halstead lost a competitive 10-round decision, but what he remembers most was being deserted by promoter Cedric Kushner at the fight venue in Sun City, which was three hours away from the Johannesburg airport. 

“I was stranded in the Kalahari Desert,” lamented Halstead. “Because there was apartheid, the passports would expire quickly, even if you were white. If we didn’t get to the airport that day, we could have been trapped over there.”

Halstead pleaded with a casino bigwig, who arranged for him, Frank Newton and corner man Sean Gibbons to get to the airport in time for their flight home. 

Because of his respectable performance against the highly ranked Coetzer, Halstead hoped to parlay that into bigger fights — the sooner the better. Instead he was matched twice in Kansas City, once again Tim Morrison, the brother of Tommy who would go to prison for rape.

Halstead said he had been chasing Tommy Morrison for the better part of the late 1980s, and was peeved by Morrison’s actions on more than one occasion. The first time Morrison reneged on a contracted bout in order to take a bigger fight in Las Vegas.

The second time, in March 1992, Morrison came calling within days of Halstead’s father’s sudden passing at the age of 47. Halstead, who by that time was making up for lost time with his father, was financially in shambles and emotionally shattered. He took the fight on short notice and despite being competitive was ultimately stopped.

The money he earned against Morrison was used to bury the father he was only then beginning to truly know.

Next up was Ray Mercer at Madison Square Garden, who Halstead described as a “big hitter,” followed by hard-punching New York favorite Alex Stewart.

The Stewart fight was on the undercard of the Riddick Bowe vs. Michael Dokes heavyweight title fight at Madison Square Garden in February 1993. Halstead said a handler came into the dressing room with a large bag of Cleto Reyes gloves, which favor punchers and which Halstead preferred.

Instead, Halstead said he was told he was going to have to wear a pair of used Everlast gloves, which made him irate. He refused to fight until longtime boxing man Al Braverman interceded by offering him some extra jingle. The cash didn’t help him in the ring, as Stewart scored a TKO.

After another TKO loss to future WBO heavyweight champion Herbie Hide in England three months later, Halstead resumed his winning ways in the Midwest.

He also sold used cars for a living before going back on the road, to Japan, Denmark and Germany.

By the time he fought his last bout, a two-round loss to Wladimir Klitschko in Germany in 1997, Halstead was physically, mentally and emotionally spent.

“I was told I was going to fight a German heavyweight named Willi Fischer, who wanted to finish out his career,” said Halstead.

“Two weeks before the fight, I’m told Fischer is on suspension and the only available opponent is Klitschko.”

On fight night, Halstead said he took one look at the giant Ukrainian, who he had just learned was a 1996 Olympic gold medalist, and told himself, “I’m done.”

Halstead was stopped in the second round and collected $5,000 despite later hearing that the promoter paid his handlers ten times that.

“My dream of being a world champion was over,” said Halstead. “It was time to call it a career.”

Halstead returned home and moved his wife, son and daughter, who were 12 and 10 at the time, to Piedmont, Oklahoma, where he ran an overhead door business.

Things were going well for the family, but Halstead got to drinking heavily in order to battle the anger and resentment he felt about being mishandled during his boxing career.

One night, in April 2002, he and his wife visited a local casino where Halstead downed seven beers. He won $2,300 and says he was “pumped up and full of myself.”

He remembers talking to a man in the parking lot, who he suspected might have had designs on robbing him of his winnings. When he went around a building to urinate, he believes the man might have slipped a mickey into his open container. 

He recalls getting in the car to head home. He blacked out — which he said never occurred before. When he woke up, he realized he had rolled the car several times. As his head cleared, he watched his beloved wife of 14 years pass away before his eyes.

Criminal charges were not filed for three months, but in the end he received a suspended sentence of 10 years.

“The guilt, regret and sadness was unbearable,” said Halstead. “In 2004, my children chose to live with my in-laws. I had post-traumatic stress disorder, but didn’t even know what that was.”

Things got even worse in 2008 when Halstead was arrested for driving while intoxicated.

Halstead was sentenced to three and a half years in prison on his daughter’s birthday. Worse than the prison sentence is the fact that his daughter has not spoken to him since the day of that arrest.

The only visitor during his prison stint was his mother, who made the long trek four times. He didn’t know how to get in touch with his son, and his anxiety, depression and guilt was excruciating. He tried to take his own life, but was stopped by a guard who happened upon him. 

“I was consumed by rage, bitterness and depression,” he recalled. “I was living in total darkness. All I wanted was to be angry and to get revenge on people I thought had hurt me.”

Because of his foul demeanor and reputation as a prizefighter, few of his fellow inmates bothered with him. Some of those who did had nefarious intentions, but he quickly put to rest any notions that he was vulnerable.

“Some people called me champ, others pushed the envelope,” said Halstead. “If they did (push the envelope), I dusted their ass. I didn’t hurt anyone in prison that didn’t try to hurt me first.”

Halstead knew that he had done wrong, but could not shake the “poison” that was eating at his soul. One day, he says, he inexplicably had a “spiritual awakening and the depression went away.”

Halstead says now that his incarceration actually saved his life. It ultimately led him through a dark tunnel and into the light. Having once felt doomed, he now finds redemption in helping others by participating in victim impact programs and other altruistic endeavors. 

He is happily remarried to a woman he has known since junior high school, and is once again working in the overhead door business.

He looks back often, but no longer with negativity. The only other two Oklahoma heavyweights of note of the past five decades, Monte Masters and Tommy Morrison, both died of AIDS. Gone too is Frank Newton, who passed away at age 59 in December 2015 from kidney failure.

Only now, at the age of 53, can Halstead fondly recall winning the World Athletic Association (WAA) “junior light heavyweight title” (super middleweight) at the age of 19 in a bout against Ron Brown in Denver. 

The WAA was created by Pat O’Grady in 1981 after the WBA stripped Sean for not defending his title against their top contender. 

Monte Masters had been the WAA heavyweight champion, but was unceremoniously stripped of the title when he and Rosie O’Grady got divorced.

Halstead was also undefeated in five weight divisions in the state of Oklahoma, and he met celebrities such as James Caan, David Letterman and Muhammad Ali.

“The odds were stacked against me, but I accomplished a lot,” said Halstead. “I gave as good as I got, and always did my best, which I’m very proud of.”

Halstead feels blessed to have a relationship with his son, and yearns for the day that he and his daughter might reconcile.

“The last time I saw her was in 2008,” said Halstead. “I understand her anger; it is a very sad and ugly situation and I take full responsibility. If she’s ever ready for me, I’ll love her with all my heart. For now, I’ll love her from afar.”

Follow us on Twitter@boxing_com to continue the discussion

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  1. Eric 05:16am, 10/25/2016

    Sean O’Grady always impressed me as a down to earth guy until I saw an old interview of John Verderosa taken in 1997 for some obscure public access television program out of New York. Kind of hard to even understand what the hell Verderosa was sayin half the time due to his slurred speech and mumbling, but he made a couple of interesting comments. He said prior to his fight with O’Grady, he had merely said hello to the Irishman and Sean totally blew him off. Verderosa claimed this is what really motivated him to turn the O’Grady fight into a street fight of sorts. Must have worked, it was this knockout loss that sent Sean packing. Verderosa also claimed that MMA would never go mainstream. Talk about a bad prediction.

  2. Irish Frankie Crawford Beat Saijo aka Gimpel 04:58pm, 10/24/2016

    Another great contribution to here. I knew a guy years ago who spent his early years in Foster Care. When foster Mom wasn’t around her natural son would torture him by chasing him around the house and shooting him with a BB gun. He never ratted the bastard out because he didn’t want to get “sent back”. It’s not easy to be in an outfit where the boss’s son is the star of the show.

  3. peter 04:52pm, 10/24/2016

    Wimpy—After losing to Evander Holyfield, the light heavyweight champion, Dwight Muhammad Qawi said, “Maybe I’m getting too old for this. Maybe I’d better look for something else to do.”  Sounds like you found that “something else”. Stick with it! Another champion—Immanuel Kant—a heavyweight philosopher once said, “Your hands are a window to your mind.”

  4. Wimpy Halstead 03:37pm, 10/24/2016

    Thanks for the comments!, Bob you covered it very well, nice work! There is always time for more living now that I am sober!! “To get the results I expected, I am the one that has to do the work”. The road has been winding, hills looked like Mountains, and striving to reach the top was all that mattered. I will continue to succeed over other roads with all I have, there is plenty of fight left in me for that.

  5. Eric 01:39pm, 10/24/2016

    O’Grady gets stripped of the title for not taking on Claude Noel, but then his dad matches him up against the dangerous punching southpaw, Andy Gannigan. An O’Grady vs. Mancini matchup would have been interesting had Sean’s career not gone sour after the loss to Gannigan. I’m sure that Sean would have defeated Noel, major brain fart by the O’Grady team.

  6. peter 11:34am, 10/24/2016

    I like the way Halstead was, somehow, willing—and able—to reboot his dark, sad life. I trust the “poison” within him is a thing of the past. This article was, yet again, another compelling human-interest story by the esteemed Mr. Mladinich…. (BTW, Wimpy—This month, I paid a pretty penny for the installation of a brand-new, automatic, over-head garage door. Selling and installing doors, as you know, is a safer way to make a buck.)

  7. didier 07:38am, 10/24/2016


  8. Eric 05:58am, 10/24/2016

    Another great article. The O’Grady clan vs. the Quarry clan would have made for a good Family Feud episode. If I remember right, at one time, Monte Masters was mentioned as a possibe opponent for a Joe Frazier comeback around ‘80-81, as was Kallie Knoetzee. Had no idea that they fed Wimpy to fierce young lions like Tommy Morrison, Mercer, and Alex Stewart, especially back to back to back, that was brutal. Looks like Wimpy was anything but a wimp with that kind of work schedule. Also had no idea that Masters had passed away as a result of AIDS. Remember watching Manson on ESPN back in the day, decent light heavy.

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