Perhaps against better judgment, we gave a guitarist/singer second and third chances to entertain our residents on a contracted basis. Twice this performer has canceled at the last minute, leaving us high and dry for entertainment and with agitated patients (and sometimes family members). But once we had to cancel a couple hours ahead of time due to a room being inadvertently double-booked. Now the entertainer is threatening to sue for breach of contract. Can he do that? Can we go after him for stiffing us twice?

It is very difficult to answer the question without first reviewing the written contract with the guitarist. The fact that the guitarist canceled two performances at the last minute were clearly breaches of the contract.

 You likely would have a good case for these breaches of the contract. But at issue is not establishing the breaches but the amount of the damages caused by the breaches. If the written contract sets forth the damages for the breach by both parties, the terms of the contract will measure the amount of the damages.

If you had hired a replacement, for example, the court likely would have found the damages equal to the costs of the replacement. If the entertainer sues you for breach when the room was double-booked, the terms of the contract or the amount you would have paid for one performance would amount to the damages of your breach caused by the double-booking of the venue. 

Moreover, because the guitarist has breached the contract, he may not sue you. Litigation is costly. If you hire a lawyer, even if you win, the costs of the litigation may exceed the damages for the breaches by the guitarist. You may decide to file a claim in the small claims court without a lawyer for the guitarist breaches.