How would Jeff Monson do against today’s HWs?

Monson was a beast...

If he can get it to the ground, he can potentially beat anyone.
 
Hard to judge his ceiling. He had a decade long stretch in which he only lost to the top guys, and beat a bunch of mostly randos with a few good wins among them.
Also had a crapton of fights and was very hard to finish after he got some experience under his belt (and before he was totally washed up and injured).

I really don't think he was that good but he was a really good grappler. Think about this though.

He choked out Prime Sergei, who was in the middle of a streak including KTFOs of Overeem and Arlovski.

He beat Prime Roy Nelson who, way later in his career, has a split decision with Lewis.

He split two with Prime Oleynik, who is still finding success today.

Then he lost to but didn't get completely destroyed by an old Fedor and a newish DC.

We won't know for sure but we can estimate that he's at best at the level of the lower top 10 today.
 
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I think that he would have the skill set to be fringe top 10 if not a top 10 fighter. Monson was a phenomenal grappler once he got the fight to the ground. The issue was his takedowns weren’t great (at least later in his career) and he had no striking to set it up. I think he’d be able to to catch a few top guys in that sweep he used to hit (see Alexander E. and Sergei wins) but for the most part would struggle to get guys to the ground.
 
Hard to judge his ceiling. He had a decade long stretch in which he only lost to the top guys, and beat a bunch of mostly randos with a few good wins among them.
Also had a crapton of fights and was very hard to finish after he got some experience under his belt (and before he was totally washed up and injured).
It's also hard to judge because during his peak (2006 to 2010) publications only had him anywhere from #12 to #20 in the world.

It's not like the originally question was asking "how would this top 5 fighter 10 years ago do today". Monson was a solid heavyweight but wasn't viewed as top 10.

To be honest peak monson in 2020 would probably be ranked about what he was then (fringe top 15 to fringe top 20)
 
Didn't notice but Monson also had a close loss to Shamil Aburakhimov who is now 40 years old and a current top 10 UFC HW.

Monson may not be a world beater but he is definitely a legitimate fighter. I think about it like this. He's like Derrick Lewis. They wouldn't scratch the top 10 of any HW GOAT list but take them and throw them into any era and they could probably scratch the top ten of that time.
 
He'd KO Stipe and go 50/50 with the rest.
 
I haven't seen any good grappling in HW UFC for a long time, they are all sloppy striking fighters. Olyinik is amazing on the ground and super good, but with Werdum leaving, the ground guys in UFC HW is very poor and low level, Monson would tap many of them out for sure. He would tap a guy like Juan Adams out with ease
 
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