I have a 20 pound destructo dog and have found that the large, sturdily built toys last the longest. She did, however, go straight for the head until she had a hole in it from which to extract miles of stuffing. Now, she still plays with the empty-headed tentacle toy. So, it IS lasting for her, but overstuffed toys are a big target.
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Review 3 for Tuffy's Alien Series Green Alien Dog Toy
It seemed really well constructed and tough which is what I was going for. My Lab likes fuzzy toys and more importantly to rip them open and pull out the stuffing. This toy lasted the longest of them all, about a week. And I kept the pieces around because he'd just sit and chew on them or play tug of war. So if you consider how long it lasted as a whole, but as pieces a couple months lol.