I have prosecuted plenty of trademarks. The logos and words are separate trademarks. For the word mark alone, Supergiant and Supermassive absolutely are likely to raise an initial LOC rejection in the same exact class of goods and services. It boils down to whether the similar words are likely to leave a confusingly similar market impression upon consumers. I legit think here it would be hard to argue around with a typical examining attorney–but the trademark office has a ton more lattitude in grants than the patent office, so it isn’t out of the question it could’ve been successfully argued or even granted initially.