So let me tell a story, I have changed the names to protect the innocent.

Hank and Barry Stoutman are longtime friends.  Barry even sought Hank’s council whenever he interviewed at a new prestigious company and Hank advises Barry to “grab the brass ring.”

Hank had Season tickets to the Steelers for many years.  Barry always bought a couple of games from Hank so he could to take his daughters.

Season after season Barry paid Hank without fail.  Hank even let Barry pick the games he wanted to fit his schedule  and opponent that he wanted to see.

Hank pays for the tickets in May each year, so in 2017 he paid for the tickets in May.  Barry did not pay Hank for the games he took in 2017 until just before he got the 2018 tickets, almost a year late.  Hank made Barry pay for the 2017 tickets before he gave Barry the 2018 tickets and made Barry promise that he would pay the ticket price promptly.

Barry then gets tickets to two games for the 2018 season for a total of $516.00 and never pays Hank.

To this day, Hank, his long time friend has not been paid.  3 and 1/2 years later and no payment.

Hank stopped at Barry’s office and Barry claimed he did not have his checkbook.  Hank stopped again and gave Barry a stamped envelope addressed to Hank, all Barry had to do was write the check and mail.  No check.

After a year, Hank sent an email to their mutual friends trying to “shame” Barry into paying the money he owed.  This backfired as Barry took offense and is now hanging his hat on the lame excuse that Hank “Crossed the line” and that is why Barry will not pay. 

Barry does not dispute the money is owed, only that since Hank crossed the line, he will not pay.

Does Hank deserve such treatment from a friend?  No.  Did Hank cross a line when he sent emails, maybe, but it had been a year that his ex-friend had made multiple false promises of payment.

Is crossing the line a valid excuse not to pay the money that is owed, no.

Should Hank go see the magistrate or just assume Barry is not a man of his word and send him a 1099 to screw up his taxes.

Thoughts?