Scott,

If winningest is not standard, I'm sure it soon will be. For fun I Googled a few other -ingest words and found examples of all of them. For example, lovingest has been used by some literary lights:

" The acutest German, the lovingest disciple, could never tell what Platonism was; indeed, admirable texts can be quoted on both sides of every great question from him." —  Ralph Waldo Emerson
 
"He told her she had been all her life the lovingest, truest, and most obedient daughter Heaven ever sent to a poor old widowed man." — Charles Reade, The Cloister and the Hearth
 
 I even tried fightingest and found informal instances on blogs:
 

"I commanded the Flying Hellfish, the fightingest squad in the fightingest company in the third-fightingest battalion in the army." —Tom Davenport
 

Ditto for singingest, laughingest, and cryingest. I remember reading in the paper a few years ago that one small town painted characters on all its fireplugs and proudly called itself "the plug-paintingest town in America."

Dick Veit

On Fri, Feb 26, 2010 at 12:36 PM, Scott Lavitt <[log in to unmask]> 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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