After looking at your regexp I took to simplifying my needs with:

$word =~ s/^[^\w\d]+(.*?)[^\w\d]+$/$1/;

My intention is remove everything that is not a letter or number up to the first letter, pull everything up till the last non letter or digit. When I look at it it makes sense, but my testing it does not work.

Update

It works on the simple example I gave for 'Wilmer!'. I was running word count with a script as the input and the odd results I was seeing were the syntax in the script. I apologize.

Except you want to strip punctuation from the beginning or end. The above regex only works if there is punctuation at both beginning and end.

If removing any trailing/leading punctuation is in fact your goal, what about something like:

use strict;
use warnings;

my $word = 'Wilmer",';

$word =~ s/^  \W*?          # ignore any leading punc 
            ( \w .*? )      # swallow everything lazily
            (?: \W+  )? $   # ignore any trailing punc
          /$1/x;            

print $word;
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Update: Mind you, at that point, a much simpler regex will likely serve you better in terms of speed and readability:

$word =~ s/(?:^\W+)|(?:\W+$)//g;
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Final update - benchmark:

               Rate     capture non_capture
capture     16561/s          --        -28%
non_capture 22861/s         38%          --
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The second suggestion is about 30% faster, on average.

Additionally, \w doesn't mean what you think it means.

I did basically your second regexp there in two steps. I will try the yours, though. I am curious the difference in speed between them. Of course I am wondering what you mean by \w doesn't mean what I think I mean.