timecatalyst,
First you need to make the flag key the first sort criteria, second ensure it is descending order not ascending, third use the spaceship operator instead of cmp because you want to treat them numerically (see perlop for details), and finally use a secondary sort by name.

@hashes =  sort { $b->{flag} <=> $a->{flag} || $a->{name} cmp $b->{nam
+e} } @hashes;
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You may also want to consider if the Schwartzian Transform is appropriate.