Hmm...I haven't really given much though to this question. I would say the "least prudent" justices seem to be Gorsuch and Sotomayor, which is funny considering they're ideological opposites. I think Roberts and Kavanaugh have prudent sensibilities, while Breyer's "pragmatism" is actually very encompassing and sweeping.
Going back a few years, I think Sandra Day O'Connor was the justice best in this mold. A lot of her opinions really delve into articulating and dissecting the specific fact patterns on which the cases turn, not making broad-sweeping generalizations that could be read as future precedent.
It’s interesting that your judicial philosophy specifically contextualizes itself, but does it very distinctly from originalism. Would you say, then, that your judicial philosophy would have been quite unwilling to rule as the Court did in
Marbury v. Madison?