Apple - Cut in CLI doesn't work as expected - returns full lines every time

You can squeeze the white spaces into a single white space in ls 's output then use cut.

ls -l /usr | tr -s ' ' | cut -d ' ' -f3

but avoid parsing ls output. Here's an alternate solution.

stat -f'%Su' /usr/*

ls doesn't use tabs, cut doesn't work with a variable number of delimeters between fields.

ls -l /usr | awk '{print $3}'

will work, or

ls -l /usr | awk 'NR > 1 {print $3}'

if you want to skip the first line (total 0 in your example).