This sounds like a series that I'd like to try out. It sounds quite similar to the Flashman Papers series. In that series the author literally took a walk-on, two-line villain from a literary classic and made a series about him.
After getting expelled from school in Tom Brown's Schooldays, Flashman goes on to be part of every British military disaster at the tail end of its empire. Since the books are written as a memoir, the reader doesn't necessarily want Flashman to make it out of the multitude of sticky situations, they want to know how he makes it out.
The Flashman papers is a pretty fun series despite how loathsome Flashman is. Especially if you're a fan of the Richard Sharpe series. Flashman is pretty much the polar opposite of Richard Sharp.