Considering it's Telltale's biggest franchise, most likely eventually. It just may be a while.
As we know, other projects are in the works right now, and Telltale's branching out into new territories. But I think Sam & Max will always be the thing they return to. Telltale, if anything, are NOT a company to forget their roots, and Sam & Max helped launch Telltale into success in the first place.
I think after all the Fables/King's Quest/etc are finished with, there's a pretty good possibility a new Sam & Max project will be on the horizon.
But there's also the matter of Telltale needing a concept. Each Sam & Max season has been progressively more expansive and impressive than the last, meaning I'm sure Telltale will want to make Season 4 even better than Season 3, and let's face it - Season 3 will be HARD to beat, especially in terms of story.
All in all, just give it time. I know over 2 years without hearing anything about the possibility of a new season seems like a long time, I'm definitely with you on that, but we're also a bit spoiled! Fans of the original Hit the Road had to wait 13 years for a new game! I think we can wait maybe 3 or 4, yeah?
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