Would Dempsey have been the hardest fight of Ali’s career in the 60s?

Discussion in 'Classic Boxing Forum' started by Melankomas, Oct 9, 2025 at 6:25 PM.


Would Dempsey have been 60s Ali’s hardest fight?

  1. Yes

    12 vote(s)
    48.0%
  2. No

    13 vote(s)
    52.0%
  1. Fergy

    Fergy Walking Dead Full Member

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    Okay mate.
     
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  2. swagdelfadeel

    swagdelfadeel Obsessed with Boxing

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    :lol: :lol: you’re not alone mate.
     
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  3. tragedy

    tragedy Active Member Full Member

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    Jack Dempsey with those damn 5oz gloves on or whatever they were is a hard fight for anything a horse, a moose, a bear, anything. Picture going 15 rounds with that its basically just a 15 round fist fight.
     
  4. Bokaj

    Bokaj Obsessed with Boxing Full Member

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    He's saying that if Dempsey managed go the distance and win 3-4 rounds he'd given Ali a harder fight than any of his 60's opponents did (I'm assuming he's referring to title opponents). You could of course argue Chuvalo did pretty much that (think I'd give George 2 rds max, though), but in principle he's correct. Dempsey could be well beaten and still do better than Ali's title opponents. The bar is not very high.

    I was also a bit confused at first. Thought he was saying that Foreman would have beaten Ali if only he'd managed to go the distance. But he meant that Foreman then would have done better than Ali's 60's title opponents:
     
    Last edited: Oct 10, 2025 at 6:29 AM
  5. Mike Cannon

    Mike Cannon Boxing Addict Full Member

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    Hi Bokaj,
    Thanks for clarification .
    stay safe buddy, chat soon.
    Mike.
     
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  6. HistoryZero26

    HistoryZero26 Boxing Addict Full Member

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    THANK YOU!!

    They all had me questioning my own sanity.
     
  7. Boxed Ears

    Boxed Ears this my daddy's account (RIP daddy) Full Member

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    When I look at what Banks and Cooper did to Ali back in the day, I think to myself, how would heavy hitters like Liston, Foreman and Dempsey do against this guy? They'd kill him. End of discussion. Bruce Lee would probably take Ali coming in at a buck forty, and maybe with modern training and nutrition, a buck 160 or with Oreos 200-300.
     
  8. Pugguy

    Pugguy Ingo, The Thinking Man’s GOAT Full Member

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    Accounting for Dempsey’s specific style, speed and power, he may well give 60s Ali his toughest fight, subject to interpretation of what that exactly is.

    I see Dempsey’s window of opportunity to win being somewhat limited - as Johnson once described Dempsey - a sabre toothed tiger for the first 4 rounds but much less so for the rounds thereafter.

    Do we have a fix or consensus on what actually was Ali’s hardest fight in the 60s for comparison?

    As presented, Cooper gave Ali that much more trouble than Liston, even though we know Liston was the better fighter by far. And that’s not just taking fight 1 but the rematch with Cooper also.

    Chuvalo won maybe just 4 rounds if that but it’s possible that Ali still might’ve described that as being his toughest fight.

    There’s also the Mildenberger fight, if only for Ali having to adjust and ultimately solve the southpaw style.
     
  9. catchwtboxing

    catchwtboxing Obsessed with Boxing Full Member

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    No. Dempsey never beat the best of his day. I don't think we can say he would be the best anything for sure.
     
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  10. Pugguy

    Pugguy Ingo, The Thinking Man’s GOAT Full Member

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    It was just a test, coordinated behind the scenes in adherence to the forum’s Sanity Clause.

    Fortunately, you passed….but only barely.

    Try to be a little bit more sane.

    I am joking, of course. :D
     
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  11. Steve Fero

    Steve Fero Member Full Member

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    He would not be the toughest. At a minimum I got Terrell Liston and Patterson would beat him. Folley and Cleveland Williams were older but won’t want to bet against them. Dempsey has good chance to beat Brian London and Mildenberger. Outside chance against Cooper and Chuvalo.
     
  12. GlaukosTheHammer

    GlaukosTheHammer Boxing Addict Full Member

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    :lol: The Mauler does not fight black men.

    Kid Blackie would but he's Kid Blackie ... get me?

    Given only a green Dempsey is willing to risk his status against a black man one has to assume no. He'd be mid.
     
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  13. Steve Fero

    Steve Fero Member Full Member

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    How did Liston and Foreman do against Ali??? He stopped them both. Cooper got a lucky punch in so what. Other then that the 2 fights were slaughters. Ali beat Patterson easily twice and Patterson KOd Cooper in 5.
     
  14. Boxed Ears

    Boxed Ears this my daddy's account (RIP daddy) Full Member

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    Okay, listen, I'm not like you and I don't check boxrec and winkleypedium every time I wanna make a comment first. This is a casual forum. Not everythink deserves its own deep dive to have a casual chitty chat, boss. Maybe if those fights was on film we could take our own words for it but we go w what we got. Ali got into serious trouble like he was pregnant a lot of those times. Liston kills him. Too big, to hard hitting, too much of a puncher-boxer style skill set, too much experience. He knew what it was like to lose. He was not living in terrifia of losing his 0 like Ali was.
     
  15. KasimirKid

    KasimirKid Well-Known Member Full Member

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    I don't necessarily agree that Dempsey would win three or four rounds, but I see your point. I agree that agualbly nobody in the 60s after Clay/Ali won the title won that many rounds against him unless it was Chuvalo when Ali was resting on the ropes.