The Greatest Middleweights of All Time

September 12, 2020

By David Martinez / Boxing Historian / dmboxing.com

Over the years I have rated fighters using many different criteria . Boxers from a specific country, and boxers in the different weight divisions, have to be the two main categories for my rankings.

Of all the weight classes through the years the one that has changed or been revised for me are the middleweights . It is clustered with greatness from the first champions – Nat Langham, Tom Chandler, George Rooke, and Mike Donovan – to the present day champions – Canelo Alvarez (WBA), Jermall Charlo (WBC), Gennady Golovkin (IBF), Demetrius Andrade (WBO), and Ryota Murata (WBA Regular) .

My rating of boxers is based on the height, peak, prime, pinnacle of their careers. Who-beats-whom at different stages of careers isn’t a factor in my “pound-for-pound” formula .

There are many situations where one fighter loses to another, and I actually rate the losing fighter with the greater “pound-for-pound” ranking at different times of each of their careers .

Here are a few examples, and these fighters lost twice to their opponents: Tunney beat Dempsey, Saddler beat Pep, Jeffries beat Fitzsimmons, Holyfield beat Tyson, Pryor beat Arguello, Herrera beat Olivares, Barkley beat Hearns, De La Hoya beat Chavez, Bowe beat Holyfield, Harada beat Jofre, and it goes on!

Here are my dozen (12) best in the 160 pound weight class of boxing. Also listed are their active years and ring records. Please note that there are two fighters who can truly fit into this middleweight category, but they are properly placed in another weight division – Sugar Ray Robinson #1 at welterweight and Bob Fitzsimmons #10 at heavyweight.

1) Harry Greb / 1913-1926 / (107-8-3 / 48 by KO)

2) Carlos Monzon / 1963-1977 / (87-3-9 / 59 by KO)

3) Tommy Ryan / 1887-1911 / (84-2-11 / 70 by KO)

4) Stanley Ketchel / 1903-1910 / (49-5-3 / 46 by KO)

5) Marvin Hagler / 1973-1987 / (62-3-2 / 52 by KO)

6) Mickey Walker / 1919-1935 / (94-19-4 / 60 by KO)

7) Marcel Cerdan / 1934-1949 / (110-4 / 65 by KO)

8) Tiger Flowers / 1918-1927 / (118-15-8 / 54 by KO)

9) Charley Burley / 1936-1950 / (83-12-2 / 50 by KO)

10) Mike Gibbons / 1907-1922 (65-3-4 / 38 by KO)

11) Freddie Steele / 1926-1941 / (123-5-11 / 58 by KO)

12) Les Darcy / 1910-1916 / (46-4 / 29 by KO)

Honorable mention: Jake LaMotta, Bernard Hopkins, Billy Papke, Kid McCoy.

My rankings in boxing have never been about trying to convert others. I respect others, as they will hopefully respect me – thank you!

Terrific list, except I do not understand the logic of Sugar Ray Robinson only being eligible for Welterweight. I agree with you that Robinson was at the zenith of his great career at Welterweight, but he should be ranked no lower than #2 at Middleweight. One can argue that Harry Greb was also his best at Middleweight. He only became a Middleweight because the Welterweight Champion at the time wouldn’t chance his title against him. Unlike Robinson, Greb did win the Light Heavyweight Title as well. Greb is arguably the greatest boxer ever, but he’s a forgotten man whose life would be resurrected in a film. Greb was quite the character, having sex in his locker room before a match, often with more than one woman. His ring walks were incredible as he wore woman’s makeup with every hair in place. He was sort of the Mick Jagger of his time with a swagger and style like no other. He didn’t care if people mocked his effeminate look entering a boxing ring. It may have very well been a component of psychological warfare in his regal arsenal. He pretended to be a drunk to get his first title bout in a bar frequented by boxing aficionados and gamblers. In reality, Greb abstained from alcohol his entire life. Greb rarely sparred, except against outlandish opponents like Jack Dempsey who he made look foolish in two sparring sessions, One round Dempsey’s trainer made last 6-minutes in the hopes Dempsey would KO Greb with the extra time, but Dempsey looked worst than ever against the indefatigable Greb, who rarely trained because he fought so often he was never out of shape. Greb wanted to fight Dempsey for his title but Rex Kearns feared him too much. His domination of Dempsey in their two sparring sessions didn’t help his cause. Greb arguably had the most unique style of any boxer in history wherein he would punch his opponents while moving around his opponent in mid-air. Only his contemporary, Peaches Flowers was able to emulate his style. It’s a shame no film exists to have documented this outstanding athlete who turned down an offer by the Pittsburgh Pirates to immediately be inserted into their lineup as a starting player. His father hated boxing and was severely disappointed that Harry turned down the Pirates lucrative offer. That’s how great an athlete Greb was. Greb’s career indicates that he may very well have been the greatest boxer in history. He drew no color line and often put his title on the line against African-American pugilists who enjoyed significant height and weight advantages. That also applies to white opponents as well. Greb never fought a single opponent that he outweighed. It’s a shame that most people don’t know his story. He defeated more Hall of Fame Opponents than any boxer in history and was champion of three divisions when there were only (8) divisions with one champ per division. Only Henry Armstrong’s feats of holding three championships simultaneously outdo Greb’s array of titles. A wise choice as the greatest Middleweight in Boxing history!

1 COMMENT

Philip Matsikoudis September 25, 2020 At 8:23 am

Terrific list, except I do not understand the logic of Sugar Ray Robinson only being eligible for Welterweight. I agree with you that Robinson was at the zenith of his great career at Welterweight, but he should be ranked no lower than #2 at Middleweight. One can argue that Harry Greb was also his best at Middleweight. He only became a Middleweight because the Welterweight Champion at the time wouldn’t chance his title against him. Unlike Robinson, Greb did win the Light Heavyweight Title as well. Greb is arguably the greatest boxer ever, but he’s a forgotten man whose life would be resurrected in a film. Greb was quite the character, having sex in his locker room before a match, often with more than one woman. His ring walks were incredible as he wore woman’s makeup with every hair in place. He was sort of the Mick Jagger of his time with a swagger and style like no other. He didn’t care if people mocked his effeminate look entering a boxing ring. It may have very well been a component of psychological warfare in his regal arsenal. He pretended to be a drunk to get his first title bout in a bar frequented by boxing aficionados and gamblers. In reality, Greb abstained from alcohol his entire life. Greb rarely sparred, except against outlandish opponents like Jack Dempsey who he made look foolish in two sparring sessions, One round Dempsey’s trainer made last 6-minutes in the hopes Dempsey would KO Greb with the extra time, but Dempsey looked worst than ever against the indefatigable Greb, who rarely trained because he fought so often he was never out of shape. Greb wanted to fight Dempsey for his title but Rex Kearns feared him too much. His domination of Dempsey in their two sparring sessions didn’t help his cause. Greb arguably had the most unique style of any boxer in history wherein he would punch his opponents while moving around his opponent in mid-air. Only his contemporary, Peaches Flowers was able to emulate his style. It’s a shame no film exists to have documented this outstanding athlete who turned down an offer by the Pittsburgh Pirates to immediately be inserted into their lineup as a starting player. His father hated boxing and was severely disappointed that Harry turned down the Pirates lucrative offer. That’s how great an athlete Greb was. Greb’s career indicates that he may very well have been the greatest boxer in history. He drew no color line and often put his title on the line against African-American pugilists who enjoyed significant height and weight advantages. That also applies to white opponents as well. Greb never fought a single opponent that he outweighed. It’s a shame that most people don’t know his story. He defeated more Hall of Fame Opponents than any boxer in history and was champion of three divisions when there were only (8) divisions with one champ per division. Only Henry Armstrong’s feats of holding three championships simultaneously outdo Greb’s array of titles. A wise choice as the greatest Middleweight in Boxing history!