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So I was looking at my Rid Landfill figure (which is a criminally under rated character, come on give us a combiner war version) and it struck me as weird that 2 of the 3 robots that make up his limbs are retools of the same mold. I know that Grimlock is meet to be the arms for Landfills main form but in his other two forms it means he has a gimpy pirate leg.
Do you think there was a time when Grimlock was ment to be a green retool of hightower? Or were the other 2 modes for Landfill just an after thought?

I don't think he was ever intended to be a retool and always was intended to serve as the arms, primary. The option to turn Grimlock into a leg was probably done after the fact and as a way to increase playability and to give another advertising point, kind of in the same vein that most of RiD Megatron's forms are pretty obviously made up on the fly. I would say that Heavy Tread and Hightower being basically retools of each other was probably a cost-saving measure by Takara.

Hightower and Heavy Load are not retools in the traditional sense: they share engineering to an extent, but they share no parts whatsoever. Also, cost saving for new molds wasn't really high on the agenda at the time, especially with Takara (remember, RiD 2001 is basically an import of Car Robots, which had no Hasbro influence whatsoever).

No, I believe it was all for the sake of symmetry. The two form the legs in the standard "Grimlock as arms" configuration, as such they'd need to be roughly the same boxy shape to create a pleasing silhouette. Compare Raiden with Devastator, or Superion and Menasor with Defensor and Bruticus, or in other words, roughly symmetrical Combiners with "cobbled together" ones.

Then there's the matter of too much of one thing being bad. Hightower and Heavy Load had similar shapes and transformation, and that was the line. Grimlock needed to be different for variety sake, plus that allowed him to make more proportionate arms.