I think the problem is that the -est superlative ending is not  
normally applied to adjectives (or participles) that have two or more  
syllables, unless the adjective ends in -y, or, for some people, -ow.  
Most two-syllable adjectives and participles form the superlative with  
"most."

So it's

nice			nicer				nicest

pretty		prettier			prettiest

shallow    		[?] shallower		[?] shallowest


but

common		more common		most common

charming		more charming		most charming

winning		more winning		most winning


Is that in any way a help?

Kathleen Ward
On Feb 26, 2010, at 9:36 AM, Scott Lavitt wrote:

> Recently a high school boy used the word "winningest," as in "the  
> winningest team," which just sounds wrong to me. It's listed as an  
> informal word in Webster's. I was trying to think of a rule why this  
> may not be SAE. First I thought perhaps the double suffix, -ing and - 
> est, but I can think of examples where double suffixes are  
> acceptable. I'm wondering if anyone can shed some light on the matter.
>
> Thank you,
>
> Scott
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