You could do
matcher = re.compile('MICHAEL89', re.IGNORECASE)
filter(matcher.match, USERNAMES)
Update: played around a bit and am thinking you could get a better short-circuit type approach using
matcher = re.compile('MICHAEL89', re.IGNORECASE)
if any( ifilter( matcher.match, USERNAMES ) ):
#your code here
The ifilter
function is from itertools, one of my favorite modules within Python. It's faster than a generator but only creates the next item of the list when called upon.