Would Jennings beating Wladimir Klitschko......

Jennings is the #6 HW in the world though, he's not (officially) a no-mark and Wlad is an aging champion at 38. I know. I never said Jennings is an absolute bum but he looked very mediocre vs Szpilka and Perez. He has no more than the puncher's chance every Wlad opponent has. And the last time someone managed to take advantage of that chance was in 2004. So yes, Jennings beating Wlad would be the biggest big-fight upset of my boxing fandom.

Of the six post-2006 fights you listed, only Baldomir vs Judah even compares to Jennings beating Wlad. And Baldomir had much more of a track record pre-Judah than Jennings has now. Ishida KO'ing Kirkland was shocking but there was nothing high-profile about that fight. Same with Khan vs Prescott. And I said "biggest high-profile upset". Hopkins beating Pavlik and Manny beating DHL weren't really upsets in my eyes. Jennings is the #6 HW in the world though, he's not (officially) a no-mark and Wlad is an aging champion at 38.

Some amazing upsets of the year from 2006-present: 2006: Baldomir W12 Judah 2008: Hopkins W12 Pavlik 2011: Ishida KO1 Kirkland And right before '06, 2005 Raheem beating Morales, after Morales beat Pacquiao. Other upsets from 06-present: Prescott-Khan, Pacquiao-De La Hoya. Of the six post-2006 fights you listed, only Baldomir vs Judah even compares to Jennings beating Wlad. And Baldomir had much more of a track record pre-Judah than Jennings has now. Ishida KO'ing Kirkland was shocking but there was nothing high-profile about that fight. Same with Khan vs Prescott. And I said "biggest high-profile upset". Hopkins beating Pavlik and Manny beating DHL weren't really upsets in my eyes.

I would be a shocker if Jennings were to snap it off, but it wouldn't be a Tyson-Douglas level event. Really, not many fights these days can reach that type of WTF just happened?!?

Definitely bigger than Wlad/Sanders. Maybe slightly bigger but you have to remember, Wlad was highly touted at the time, Sanders was semi-retired and the two Klitschkos were viewed as the future of the division, HBO were investing huge money into Wlad. If Jennings comes out and blasts Wlad away, then yeah, it would be much bigger. A points win is on par.

Yes its a great up set the heavyweight will be back in American hands if he does

Not as big as that but it would be pretty big, more Sanders/Wlad really. Definitely bigger than Wlad/Sanders.

Yes, i'd definitely say so. Jennings might be highly ranked, but it's on the basis of beating fringe contenders like Liahkovic, Splizka & Perez. And to me the difference between champion and #6 or whatever he is might as well be the difference between champion and #50. Wlad is in a completely different league and I honestly think 16-1 is a compliment to Jennings.

naa,,,if wlad were a few yrs younger but at 39 yrs old it shouldn't be shocking if wlad were to get upset altho I doubt Jennings is the guy to do it

douglas was at least a massive man with power. he had a good jab, too, and presented a difficult style for tyson. jennings is a big guy, but he's really not a puncher. wladimir's weakness is dat chin doe. but yes, it would be a huge, huge upset. one of the biggest in recent memory. i don't think jennings has a prayer, unless wladimir gets old overnight, or careless and clipped with something he can't see. jennings has an athletic style. he tries to use the ring. wladimir does very well with enough time to think, and institute the jab. he'll have time in this fight. i cna't see jennings coming to wladimir with any real consistency, the way you've got to do to pressure a man of that size.

Be one one of the greatest HW upsets in recent time? No one is giving Jennings a shot. The western world is craving for more HW champs, could it potentially even reach Douglas vs Tyson level? Not as big as that but it would be pretty big, more Sanders/Wlad really.

Some amazing upsets of the year from 2006-present: 2006: Baldomir W12 Judah 2008: Hopkins W12 Pavlik 2011: Ishida KO1 Kirkland And right before '06, 2005 Raheem beating Morales, after Morales beat Pacquiao. Other upsets from 06-present: Prescott-Khan, Pacquiao-De La Hoya. hopkins beating pavlik was hardly an upset. not to me, anyway. ishida/kirkland - it was shocking yeah, but kirkland had never been some world class fighter like wlad is right now. he's been undefeated for 10 years, next to floyd he's perceived as the most unbeatable man in the game right now.

I don't know if it will be one of the biggest of all time because I'm not that big on boxing history, but I can safely say it would be the biggest high profile upset since I started following boxing (2006). Some amazing upsets of the year from 2006-present: 2006: Baldomir W12 Judah 2008: Hopkins W12 Pavlik 2011: Ishida KO1 Kirkland And right before '06, 2005 Raheem beating Morales, after Morales beat Pacquiao. Other upsets from 06-present: Prescott-Khan, Pacquiao-De La Hoya.

he has a chance...

wlad losing to anyone would be a huge upset imo

I don't know if it will be one of the biggest of all time because I'm not that big on boxing history, but I can safely say it would be the biggest high profile upset since I started following boxing (2006).

I don't think it would be such a massive upset. Jennings is a top 5 contender. He's undefeated, coming off a win over Mike Perez. He has a reach advantage over Wlad, He's 8 Years younger and he will come to the ring in great physical shape. Wlad will be the hot favorite but Jennings does have a chance.

Wlad's age of nearly 40 years old, would be a huge part of the conversation as to why he lost. Tyson was 24 years old and in his prime, undefeated. I give Jennings no chance, but Wlad being 38 waters down any upset. Like Mayweather and Marquez also. Any upsets against them at this point, is watered down because they are almost 40. 40 is not an age for athletes even though there are exceptions, it's still seen as an advanced age for sports except Golf.

no its not an upset because clinchko sucks. in an honest sport without clinching jennings would probably be the favorite but we know that won't happen and he won't even be allowed to throw punches so its a waste of time. prepare to be disappointed like in every wlad fight.

Don't know about the biggest upset. Tyson was undefeated and a total beast when Douglas beat him. Wlad is a beast too but he has been beaten before, although not in ten years. It would be a shock to me after his longevity, but bigger than Douglas-Tyson, Chavez-Randall I, McCall-Lewis I, Duran-Laing, Barkley-Hearns I? I don't think it would be as shocking as those. Jennings is a high rated contender and unbeaten. It definitely would be huge. I don't expect it to happen though. Even Wladimir said Jennings is like Rocky Balboa lol. I just don't see any scenario with Jennings winning. W Klitschko will have to age considerably in one night for that to happen. Would be a huge upset but nah not on that level. Jennings is Top 5 I believe. Don't think Douglas was Top 10, not sure. I know Rahman and McCall weren't. Good comments.