Hi Narcissus
Thanks for reaching out via the forum. It sounds like you have a lot of experience in the gym and with weights so I feel your frustration with this issue. A winged scapula is due usually to an issue with the long thoracic nerve of the shoulder and/or weakness in the Serratus Anterior muscle. If the long thoracic nerve is damaged or bruised it can cause paralysis of the serratus anterior muscle and wing of the scapular or shoulder blade.
It could well be the case that your scapula on the left (like mine) has been a little compromised for a long time and only now that you are having an issue are you noticing it. Often this would not show up on a scan and actually if an MRI is pretty clean then that's great as there should not be anything to major going on. If the serratus anterior muscle is having an issue then this will affect your pushing (bench) movements. But a true long thoracic nerve issue would also cause some pulling issues too as the scapula would be having a hard time to hold itself in a stable position while you recruit the muscles attached to it. So your presentation might not really be a true winging issue but that the winging is a sign of some asymmetry that has been creeping in over time and now is proving to be symptomatic.
One thought also is that if your AC Joint (Acromioclavicular joint) is a little out of place then the body will not be pulling or pushing with normal strength. It's easy to upset that joint at the scapular end (and also at the sternal end) with pull ups etc. and you might not even know it.
My approach to this would be to back off the weight for now until you feel both sides are contributing equally to the exercise. Be strict with your form on that. And as the nerve might be a little trapped in the neck musculature perhaps get some deep tissue massage for a few sessions to release the area. I'd think something 1-2 times a week for a couple of weeks in combination with the reduction in weight on the bar etc. Lay off the chins etc unless you're using a machine assisted version.
These things can be frustrating which is rather annoying but in my experience that have often been a long time coming and only towards the later stages do they become symptomatic. Let us know how you get on and I can provide some more feedback.
regards
PB