Predicate logic — the great leap. Quantifiers (∀, ∃) and the function/argument analysis are the biggest advance since Aristotle. First-order logic is the logic of all modern mathematics and computer science.
His grand program failed. Frege's logicism — that mathematics reduces to pure logic — was wrecked in 1902 by Russell's paradox, which showed his foundational system inconsistent.
Unread in his time. Almost no one noticed him until Russell and Wittgenstein. (And honestly: his late diaries record vicious antisemitic, anti-democratic views — the logic stands; the man does not.)
Here is the move Aristotle and Boole could not make. Below is a small world of objects, each red or blue (click to flip one). A quantifier lets a single statement range over the whole world: ∀x "for every x…", ∃x "for some x…". Watch the quantified sentences decide their truth as you change the world — something term logic, locked to whole categories, simply cannot do.
The deeper gift is relations and nesting. Click the grid to set a relation R(x,y) — "x → y". Then two sentences that use the same symbols in a different order say utterly different things: ∀x ∃y R(x,y) — "everyone relates to someone" — versus ∃y ∀x R(x,y) — "someone is related to by everyone." "Everyone has a mother" is not "someone is everyone's mother." No logic before Frege could even tell them apart.
"Every good mathematician is at least half a philosopher, and every good philosopher at least half a mathematician." — Gottlob Frege
Frege spent decades on one dream: to derive all of arithmetic from pure logic alone — logicism. As the second volume of his Grundgesetze was at the printer in 1902, a letter arrived from a young Bertrand Russell with a single, fatal question. Consider the set of all sets that do not contain themselves. Does it contain itself? Try to answer.
Gate kept on. Russell's paradox didn't dent Frege's logic — quantifiers and predicate logic are untouched and immortal. It killed his foundations: the unrestricted "set of all things satisfying a property" his system allowed is self-contradictory. Frege, with rare honesty, appended a note saying a cornerstone of his edifice had given way, and never really recovered the program; arithmetic was later refounded on type theory and on the ZFC axioms that forbid such sets. Two further honest things: he was almost entirely ignored in his lifetime — modern logic flows from him only because Russell, Wittgenstein and Carnap carried it forward — and his late diaries (1924) record virulent antisemitic and anti-democratic views. The greatest logician since Aristotle, whose foundations cracked, who went unread, and whose character at the end was repugnant. The work is permanent; the rest is told plainly.