Leave it to someone with a name like "Smiley" to ask a dental question!
My experience has been that brushing a dog's teeth is not a natural activity that a dog loves! When we first started we had this little poodle, Bobby, who had the worse halatocis(sp) I had experienced with a dog. I bought him some doggy tooth paste and finger brushes. I commenced to brush his teeth and he commenced to fight me! It was a lose, lose situation!
What I have found is that you have to get your dog use to the idea that you are going to be in his mouth. Start by just rubbing his lips, then after a couple of days of this, rub his teeth. Then introduce some doggy tooth paste. My vet only carries one brand, so I have only tried that. It's called something like C.E.T..... it's poultry flavored, yum! It takes me a couple of weeks to get a brush into the dogs mouth. You of course only want to use doggy tooth paste, because most of us cannot get our dogs to spit... and swallowing toothpaste can be upsetting to a tummy.
I do not do a good job on the teeth end. There are other things you can do that help... not necessarily replace.
Dry food is best for their teety.
There are Dental treats that help as well.
There is a product that you can add to water to help fight plaque.
Vet's offices also offer teeth cleaning. I believe they put the dog under and do a good cleaning.
Let us know how it goes for you and Wrigley!