Can lifetime learning expand behavioral diversity over evolutionary time, rather than collapsing it? Prior theory predicts that plasticity reduces variance by buffering organisms against environmental noise. We test this in a competitive domain: chess agents with eight NEAT-evolved neural modules, Hebbian within-game plasticity, and a desirability-domain signal chain with imagination. Across 10~seeds per Hebbian condition, a variance crossover emerges: Hebbian ON starts with lower cross-seed variance than OFF, then surpasses it at generation~34. The crossover trend is monotonic (\r{ho} = 0.91, p < 10^{-6): plasticity's effect on behavioral variance reverses over evolutionary time, initially compressing diversity (consistent with prior predictions) then expanding it as evolved Perception differences are amplified through imagination -- a feedback loop that mutation alone cannot sustain. The result is structured behavioral divergence: evolved agents select different moves on the same positions (62\% disagreement), develop distinct opening repertoires, piece preferences, and game lengths. These are not different sampling policies -- they are reproducible behavioral signatures (ICC > 0.8) with interpretable signal chain configurations. Three regimes appear depending on opponent type: exploration (Hebbian ON, heterogeneous opponent), lottery (Hebbian OFF, elitism lock-in), and transparent (same-model opponent, brain self-erasure). The transparent regime generates a falsifiable prediction: self-play systems may systematically suppress behavioral diversity by eliminating the heterogeneity that personality requires. \textbf{Keywords: Baldwin Effect, neuroevolution, NEAT, Hebbian learning, chess, cognitive architecture, personality emergence, imagination