Did you stay friends? Did he just suck at his job or was his attitude and work ethic poor? One different decision and it's possible you could have been my boss! That's funny.I only ever fired 1 man. The upper management always gave me the black sheep and told me "we know you'll make em a good hand and work or fire em".
That kinda sucked but it was true, only 1 took advantage of me every chance he got while on probation and we were hunting buddies before he hired on. Firing a good friend was tough as nails but he earned it, fair and square and upper management saw it playing out so I could not give him another inch.