Quando mai literally translates to "when ever" or "when ever will that happen?" but in Italian slang, it's often used to mean "no way" or "never."
In this song, Gemitaiz uses it to express defiance and refusal. When told "vattene" (go away), he responds with "fraté ma quando mai?" (bro, no way!), emphasizing his strong will and determination not to back down or leave. This makes it a very engaging and memorable phrase.
In "Quando Mai," Gemitaiz paints a picture of a life spent fighting against the odds. He looks back on his youth, feeling that the place he was born held him back and that he wasn't prepared for the struggles ahead. He describes a dark and hopeless environment where he feels judged unfairly, trapped "with a noose around his neck." He compares achieving his dreams to the impossible task of finding a field of four-leaf clovers.
Despite the bleakness, the song is a powerful statement of defiance. Gemitaiz refuses to give up or change who he is, even as he sees friends around him surrender. He criticizes those who sell out for a salary, becoming like "the living dead." The title, which translates to "When Ever?" or "No Way!", is his response to those who tell him to leave or quit. It's a declaration that he will stand his ground and stay true to himself, no matter what.