Speech anonymization is commonly evaluated using averagecase metrics such as the equal error rate, which can hide large disparities in re-identification risks across individuals. In this paper, we conduct a large-scale per-speaker privacy analysis using a linkability-based metric under a worst-case scenario. Nearly 5,000 speakers are evaluated across multiple anonymization systems, attacker architectures, and conversation lengths. While linkability scores are highly polarized at the speaker level, the sets of easy to re-identify and hard to re-identify speakers vary substantially across configurations. We show that no single factor explains speaker vulnerability. Instead, the re-identification risk emerges from the interaction between the attacker, the anonymizer, and the amount of available speech. These results challenge the notion of intrinsic speaker-level privacy risks and emphasize the need for evaluation protocols that are explicitly conditioned on the attacker and anonymizer.