This paper presents data on left-dislocation (LD) in Wisconsin Heritage German (WHG). Data are drawn from interviews conducted with six speakers, who were recorded in central and eastern Wisconsin in the 1940's by Prof. Lester W. J. Seifert. Modeled as the addition of pragmatically conditioned, left-dislocated phrases (XPs), LD in WHG provides evidence for a pragmatic alternation between neutral and [+focus] interpretations. Analysis of the data shows that 5 of 6 WHG speakers in the corpus employ LD only in pragmatically conditioned environments such as topical conversations with the interviewer, and during story-telling. These same 5 speakers do not employ LD during translation tasks that lack contextual factors such as extended narration; and similarly when speech lacks a discourse element triggered through interactions with an interlocutor, e.g., during English-to-German translation tasks. Previous literature has suggested that the syntax-pragmatic interface may be vulnerable to language change, cross-linguistically, and that less proficient heritage speakers (HSs) may pattern more like L2 learners than L1 speakers (Sorace, 2011; Benmamoun et al., 2013; Polinsky, 2018). However, the presence of pragmatically conditioned LD in the early 20th century WHG suggests both the acquisition of a full, functionally communicative HL grammar, as well as a robust use of (spoken) German in Wisconsin, such that context-dependent, pragmatic elements in the HL grammar are acquired and used within a community of HL speakers.