Leroy Jeffery - First Man to Beat Howard Winstone

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Taansend
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Leroy Jeffery - First Man to Beat Howard Winstone

Post by Taansend »

I doubt if I'll get too many replies to this random question.......

Just going through old records & noticed that Winstone was a fantastic 34-0 when he fought American Leroy Jeffery 19-4 in Leeds in what I assume was expected to be a warm up fight.

Jeffrey had stopped 15 fighters but hadn't beaten anyone of note & lost 3 out of 4 fights in an 18 month spell before meeting Howard.

Winstone was ranked 1st or 2nd at Featherweight for Davey Moores belt.

Then BOOM, Winstone gets decked three times & stopped in round 2 in what must have been a massive upset.

The thing is, other than Boxrec, I can't find any information about Jeffrey. He lost his next bout bringing his record to 20(16)-5(0) then vanished. His pro career only lasted 5 years.

Has anyone ever heard of him or know anything about him? He was from Saginaw Michigan.

Cheers
Controversial
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Controversial »

Good find, I can’t find much either, other than what’s on his wiki page on this site. Looked like he was a big puncher so guessing he just caught Winstone early and got the upset win.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by elmersalsa »

If you beat a guy like Howard Winstone in his prime, you must be very good. Winstone was a hell of a fighter.
Taansend
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Taansend »

And he only had one more fight after beating Winstone then vanished.
Controversial
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Controversial »

Maybe something happened to him, injury?
Taansend
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Taansend »

Controversial wrote: 14 Nov 2025, 23:39 Maybe something happened to him, injury?
Could be. Or death. Or Prison. Or went to college & became a Doctor.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Woller »

Quote from Brian Hughes book on Howard Winstone:
"According to eminent boxing reporter Reg Gutteridge, Jeffrey retired after his losing fight against Billy Calvert, because he suffered a detached retina. However, there were reports from the States that Jeffrey retired from boxing because af injuries suffered in a serious car accident".

I can recommend Brian Hughes book "Reaching for the stars"
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Controversial »

Woller wrote: 15 Nov 2025, 06:50 Quote from Brian Hughes book on Howard Winstone:
"According to eminent boxing reporter Reg Gutteridge, Jeffrey retired after his losing fight against Billy Calvert, because he suffered a detached retina. However, there were reports from the States that Jeffrey retired from boxing because af injuries suffered in a serious car accident".

I can recommend Brian Hughes book "Reaching for the stars"
Nice one Woller
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by scribbs73 »

Boxer's Career May Be Over

The Detroit News
Saturday, Dec 08, 1962 Page B & 4B

By PETE WALDMEIR

Lightweight Leroy (Honey Boy) Jeffery's career may be ended - in Michigan at least.

The 26-year old fighter will be examined by Dr Robert C, Bennett, physician for the Michigan Boxing Commission, today. The doctor, who recommended to the commission last spring that Jeffery's license not be renewed, will be conducting the second examination of the boxer within 24 hours.

Jeffery was examined at Receiving Hospital yesterday for a reported head injury suffered in a bout last month in England. Dr Bennett said that X-rays taken at the hospital failed to show any skull damage.

"The hospital made a preliminary diagnosis of epilepsy." Dr Bennett explained.

"However, the doctors there had no access to Jeffery's boxing background.

"The fighter was stricken yesterday morning with what appeared to be a seizure, His wife called police to take him to the hospital, but when they arrived, he had recovered sufficiently to go himself.

"There is no evidence that he was hurt in England, but I'm going to find out what is the matter with him. I recommended to the commission last spring when I examined Jeffery after his last fight here that his license not be renewed.

"Jeffery was rubbery then and there was evidence of deterioration. I don't think he'll ever fight again, in Michigan at least."

Jeffery, who stands 5 feet 4 and weight 130 pounds fought here lasy May 21, knocking out Wesley Kidd in the fourth round of a scheduled eight-rounder.

Jeffery's manager, Charles Russell, booked for a bout with Howard Winston [sic], Engalnd's No. 2 lightweight contender, at Leeds, England, last month.

Jeffery knocked out Winston [sic] in a upset, but lost a 10-round decision to Billy Calvert in Manchester a week later. he returned home complaining of headaches and a badly sprained hand.

"The boy may be suffering the dalayed effects of a brain concussion," Dr Bennett said.
"Sometimes they come four to five months after the blow is struck."

Originally from Saginaw, Jeffery has been fighting professionally since 1957, has lost just four time in 25 bouts and has made two national television appearances.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by scribbs73 »

Obituary

The Detroit News
Saturday June 8, 1985 Page 7B

Leroy Jeffery
Former Detroit professional boxer

By James L. Kerwin
News Staff Writer

Leroy Jeffery,s promising career as a professional boxer ended abruptly in the early 1960's when he too(k) [sic] many opponents bigger then himself.

Mr Jeffery, 50, who died Wednesday in the Veteran's Administation Hospital in Allen Park, added extra pounds to his 5-foot 4-inch frame to qualify for the lightweght division after he failed to find enough competition in bantam and featherweight bouts.

As an amateur during th 1950s, he won 211 fights, knocking out 187 opponents and losing only six times, to reign as a two-time Golden Glove champion in Detroit and the national Golden Glove bantamweight champion in 1953. He won a national collegiate crown as a freshman at Michigan State University in 1955.

Once rated as one of the "city's best young boxers," Mr Jeffery using the nickname of " Honeyboy" - won a string of professional bouts before serious head and eye injuries forced him to retire in 1962. In almost all his professional bouts, some of which were televised nationally - he was forced to give his opponent the advantage of size.

After retirement, he began a career as a Detroit real estate broker while helping supervise foster homes and mental health programs.

Surviving are his wife, Ollie; daughters, Doressa and Mrs F Annette Hampton; sons, Leroy Jr. and Andre, and an adopted son, Norman; his mother, Mrs Isabell Jeffery; two granddaughters, and a sister.

Visitation is scheduled for 5 or 6pm. Sunday at the Pope Funeral Home, 8450 Plymouth in Detroit. Services will be held at 11a.m. Monday in Peace Baptist Church, 13450 Goddard, Detroit.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Taansend »

Woller wrote: 15 Nov 2025, 06:50 Quote from Brian Hughes book on Howard Winstone:
"According to eminent boxing reporter Reg Gutteridge, Jeffrey retired after his losing fight against Billy Calvert, because he suffered a detached retina. However, there were reports from the States that Jeffrey retired from boxing because af injuries suffered in a serious car accident".

I can recommend Brian Hughes book "Reaching for the stars"
Thank you, very very much.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by JC »

Thanks for the articles, scribbs. :TU:

Sad story overall, dying at 50.

Clearly had some talent, although 187 KOs in 211 amateur fights sounds unlikely.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by Taansend »

scribbs73 wrote: 16 Nov 2025, 16:28 Boxer's Career May Be Over
And thanks too.

It just shows the difference in those days.

In November 1962 Winstone loses his undefeated record in a bad KO loss.

The bloke who beats him loses himself three weeks later to another UK fighter.

Winstone then fights six more times in the next 8 months, picking up the European title along the way, before beating the man who beat the man who beat him.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by bennie »

Winstone and his manager Eddie Thomas did push for a rematch with Jeffery but the American was obviously unavailable after the Billy Calvert beating. Winstone would remind people that he scored three wins over Calvert whenever Jeffery was mentioned.
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Re: Leroy Jeffery - First Man to Beat Howard Winstone

Post by 2294933 »

Hello
My name is Tamar V. Jeffery. I am the granddaughter of Leroy Jeffery. I think it's awesome that people are still inquiring about him. I knew he was a boxer, rode Harley Davidson motorcycles, and had his own real estate company. I didn't know a lot about his boxing career until I started doing research on him a few years ago. I watched the documentary on Howard Winstone years ago. I wish there was footage of the fight so I could watch it. He settled down and retired from boxing when he returned to the US. I think he was told he shouldn't box anymore by physicians due an injury but I would need to ask my mom or great-aunt(his sister) to confirm. I was 6 years old when he passed away from cancer in 1985 so I don't have many memories of him. Does anyone know how I can obtain footage of any of his fights?
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