You're using the needleless syringe with the tip cut off, right?
Wrap him like a burrito and tuck him under your arm, like a football. It helps if you do it on the kitchen counter where he can have his feet on something and you're just trying to control him rather than hold him.
Have the other person insert the syringe into his mouth at a 90 degree angle. It should look like you're trying to push it through the other side of his mouth. Put it in just behind his front teeth and in front of his back teeth, and insert it half an inch or so. Then turn it so it's pointing toward his throat, insert it another quarter of an inch, and give the medication, about .2 cc at a time. Don't take the syringe out in between. If he's chewing, he's swallowing.
You can get quite a firm grip on his head to do this, but try not to put pressure on his lower jaw -- you don't want to dislocate that.
You can also flavor the stuff with something he really likes. I used to mask the taste of medicine for mine with cilantro. But some pigs will take medicine pretty easily if you just offer them the syringe.