Ah, OK. You're basically just mashing them. I didn't think there was any realistic way to get a contact that big into the little Radio Shack tool (which, while remarkably versatile, is not really meant for stuff this big) and do a normal wrap-around crimp. You can probably get a lot more force than the normal needlenose trick, and hey, if it holds, it'll work.
The crimp tool will probably not last nearly as long as it might when using it on "appropriate" size contacts, but they're a whopping nine bucks, so who cares.
FWIW, the PA-21 I have crimps this series pretty well (down to the #18 size contacts - it can't do the ones intended for giant wires correctly), but it's like a $60.00 tool.
Despite having a couple of generally nicer tools, I actually keep one of the Radio Shack ones around. It actually works better on certain kinds of contacts (the ones where the jacket retension is meant to form a circular opening and has the two prongs offset e.g. Harwin M20) than my PA-21 and PA-09 does. Price is certainly right, and they're easy to get.
If you want a nicer tool for this series, Molex has a largeish "Universal" tool. It's commonly found in KK and 0.093/0.062 field service kits and is reasonably priced standalone (~$30, I think). It does OK on things about this size. It looks like the Molex contacts for this series don't have the excessively long insulation prongs that the AMP ones do, which is what makes the real crimping tool somewhat essential.