"Winningest" presents an interesting problem in language change, as Bruce suggests.  The pattern in English of /Ng/ vs. /N/ alternation, where /N/ represents the velar nasal sound in "sing," lays out roughly as below:

Morpheme-internally English has /Ng/, as in "finger," "dangle," or "Tonga."
Before a vowel-initial inflectional suffix, English has /Ng/, as in "longer," "strongest."
Before a vowel-initial derivational suffix, English has /N/, as in "singer," "hanger."
Word-finally English as /N/, as in "sing," "long," etc.

It could be argued that /Ng/ vs. /N/ represents a productive morphophonemic alternation.  "Winningest" would support this claim, since -ing is a derivational suffix and so does not have a /g/ before an inflectional suffix.  "Winninger," whether it occurs or not, would behave the same way for the same reason.

In Old English there was only /Ng/ and /Nk/, no bare /N/, since /N/ was what /n/ became by assimilation to a following velar (/g,k/).  In Middle and Modern English the final /g/ was lost in the contexts given above where /N/ now occurs by itself.

It can thus be argued that /g/-deletion is a regular morphophonemic rule in Modern English.

As a side note, this /g/-deletion is distinct from what is popularly referred to as "dropping "g," the free variation between "walking" and "walkin'."  This variation, which actually has nothing to do with /g/-deletion and refers instead to an orthographic practice, probably arises from the merger in Middle English of Old English present participles in -end- and gerunds in -ing.  The final /g/ of /-INg/ was lost as illustrated above, since it was word final, giving the form /-IN/, as in "walking."  The loss of the final /d/ of the -end suffix produced the form /-In/, as in "walkin'."  The -ing/-in' variation reflects the distinct sources of the Modern English present participle, and although our spelling makes it look like dropping of /g/, phonologically there is no /g/ to drop.  The -in' form simply has a different historical source.

Herb






________________________________
From: Assembly for the Teaching of English Grammar [mailto:[log in to unmask]] On Behalf Of Dick Veit
Sent: Saturday, February 27, 2010 9:26 AM
To: [log in to unmask]
Subject: Re: Double suffixes

Another observation: participles loving, winning, and losing have superlatives but not comparatives: The Canandian women's ice hockey team was the winningest in the Olympics, even winninger than the Americans.

Dick

On Sat, Feb 27, 2010 at 3:32 AM, Webmail bdespain <[log in to unmask]<mailto:[log in to unmask]>> wrote:
Just some more observations.

There is a certain phonetic similarity about the two-syllable words that attract the -est suffix:  they seem to end in an unstressed vowel or sonnant, e.g., able, clever, common, feeble, gentle, narrow, shallow, simple.  Some single-syllables that end in -ng make the g hard, e.g., long (longest), strong (strongest).  The fact that the adjective forming -ing does not seem to do this suggests a separate allophone or morphophonemic rule.  Also the -y adjectives that attract -est can often have another syllable added to the front, as, unhappiest, untidiest.  This does not seem to be the same for loving or winning: *"the unlovingest disciple", ?"the unwinningest team this season."

Bruce
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