He definitely would. Now, whether he could succeed is a different question. The problem is:
If you made a faithful remake and attracted his patrons (former and current), he would definitely have a case against you. Targeting his audience and the resulting outflow of patrons would be proof of that.
If you tried to make the remake sufficiently different so that he would not have a case against you, you would be writing for a different audience and wouldn't attract his patrons.
I don't think a remake is coming for at least a few years until gumdrop is out of the picture, and then nobody will remember this game anyway.
The character designs are his. The claim of free use means the IP has to be transformed in such a way that it brings new dimensions to that content. If a person is just using the same character designs (or those easily recognizable as such) without permission and making a porn product - that is not likely to pass any sniff test.
And remember that what you are talking about is a legal defense that can only be determined by arbitration or a court of law. It's not a "get out of jail free" card that one can waive and think there won't be repercussions.
Whether he would succeed is not the question that needs answered. It's whether or not he could keep the claim tied up in negotiations and/or court. The entire time it would be in that limbo, the remake would sit idle and without the ability for the creator to receive any funding under a cease and desist order. At the same time the creator of the remake would need to spend money on attorney fees, expenses, and court costs which would greatly outweigh any eventual earnings (through sales or donations). And should the remake creator lose, they would be subject to paying everyone's costs (theirs and gumdrop's) as well as any financial damages the decision carried.
Gumdrop could actually end up receiving more money in a copyright claim against someone than he has the entire time this product has been in development, if he had the right legal team.