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There's mostly downside for them because a significant fraction of their members are not fans of the 2nd amendment.

The closest I think they've gotten to gun cases is probably this one, which was more of a 4th amendment issue:

https://www.aclu.org/cases/caniglia-v-strom

There have been others. I join in the disappointment at the sad turn the ACLU has taken. But they have been consistent in their opposition to no-fly lists, as an end-run around due process, and have applied the same argument against proposals to create similar no-gun lists. They are right in both cases.

Then there was this case, which was mainly 1st amendment, but with strong 2nd amendment ingredients:

https://lee-phillips.org/aclu2/

Didn't the NRA help form early gun control laws?

Yes but for all practical purposes it's not the same organization anymore.

The NRA is bankrupt and about to be dissolved.