[grumps]

This will require you to weigh the risks. While I like the approach, you'll have to trust your gut. You're gut is going to have to say that MGMT will believe the cost of replacing Jerry < the cost of replacing you irregardless of most personal relationships. Especially if the loss of Jerry could negatively impact revenue more then the loss of you as an employee. There's also a moral factor if you're gone and above is cold hearted logic.

[throwaway1980s]

The moral factor hits home, as if I did this, then one of us would be out of a job, regardless. It feels like a failure regardless of the outcome.

I also know from prior conversations that it would result in me being the one walking, as while my position is important and my tenure at the company longer, I would be easier to replace vs Jerry.

[lostdog]

It is a failure, but it's not your failure. Your boss failed to bring about a positive outcome, and the only thing in your power is to deprive them of an employee that they clearly don't deserve. Good luck!