Hi All,

I have a small restaurant in a historic district of a major metro area in the US. If state becomes relevant, I will edit and disclose. I treat employees like they’re family, and after the first few months of shuffling through employees who didn’t have an appreciation of that and just wanted to abuse it, it has worked out great and we have an awesome staff who are truly friends.

I hired a younger guy about 8 months ago for an assistant kitchen management position that was maybe out of his depth, but I’m a big fan of giving people opportunities to show what they’re made of. This was a salaried position, but he was still only working around 40-47 hours. He came into a situation where he was in urgent need of money, so I lent him some money with the deal that a small portion would be deducted from his weekly check, and we worked out a plan where if he went above 45 hours, I’d pay him a bit extra hourly up to 60 hours (15 additional). Almost immediately, he began taking advantage of it. Coming in way earlier than necessary, staying way later, etc… and racking all the way up to 70+ hours. I paid it because even though I was upset, he was ‘there’ for those hours and the last thing I needed was a labor claim.

This went on for about 2 weeks before I sat him down and told him that wasn’t part of the deal, and he cannot go above 60 hours, as it was a favor to him because I like him, and not hours that we needed. On top of that, he wasn’t a stellar employee by any stretch of the imagination and even less was getting done than when he started at almost half the hours. This was when he voiced to me that the management duties were too much for him (it really wasn’t any added work, as I was already having to take on the ordering and do most of his duties other than actual line work). I agreed to transfer the title/responsibility to another worker who I adore and who has already been helping me with this, and she’s been a saint before and since this. When I explained to him that he was no longer a manager and that he cannot go above 40 hours or else it will cost me even more money that I cannot afford to put out, BUT that he could keep his (already overpaid) weekly base amount, he went on a war path. Telling other employees he was going to quit, calling out minutes before his shift, and generally doing even less than he had already been doing previously. I should have fired him, but as I said earlier, I feel for the situation he’s in. I had a long talk and offered my last olive branch in telling him that I was willing to over look him trying to basically cause a mutiny in the kitchen, telling other staff he was going to quit, and doing hardly any work if he was willing to come in the next day and give some effort and put it behind us. He agreed but of course went right back to it.

He didn’t speak to me for nearly a week while I was finding his replacement, and when he reached out to me 4 days ago, he was being nice until he told me he’s in a bind and really needs $3300 (on top of the almost 2 he already owes me). I told him that not only could I not afford it, with him telling everyone he’s leaving and his current attitude, I won’t. He has now called out the last 4 days minutes before his shift was to begin. I half expected this, so I already arranged for coverage. I’m 99% sure he wants me to fire him so that he can apply for unemployment.

My question is at what point can I just tell him to walk and be relatively sure he’s got no case for unemployment? I’ve been far too kind to him already, but my state seems to pay out damned near every claim.

Sorry for the novel, and thank you for your time.