Learn the tricks of the Vet: Hold his snout up and he’ll swallow peacefully.
There is a specific finger position that helps in this. To start, I would take some time to start calling him over to you, then pet his head, and get him used to your hand being under his snout in a loving sorta way. After a few days of this it will be easier and stress-free.
I had to do this with a pug. It’s possible. there is a point on their chin that will make them choke, and a point that will make them not even feel the pill.
I have recently started giving my 9 YO Shepherd Lab X glucosamin pills. The are large enough to choke a horse, so I break them in two,hide them in bacon strips and she takes the treat. After she has chewed a little bit and is preparing tosppit out the pill, I gently hold her snout up and closed and she eventually swallows the pill.