Med advice?

I find it easiest to brace my cats between my legs and then have better control of their mouths. Just stick the dropper behind the canine teeth (cats have a space there) and squirt. Use one hand to squirt and another to control the head. At least that is what works for me.

I sort of put them in a headlock and stick the dropper in the corner of their mouth. Of course, they don't like it but they have no choice...

The only thing that I can think to add to Amanda and Debbie's advice would be to wrap him in a towel like a kitty burrito if he has claws. Then brace the pissy burrito between your knees that way your hands are free and your legs aren't getting clawed up. I had to do this with Izzy. And by the sounds she made while I was trying to administer her eye drops...I was very glad she was wrapped up.

No advice, but I don't envy you.

If Boomer loves wet food, and as a last resort, if he's a spitter (Patches is like that), you can mix the liquid meds with some stinky wet food.