Overexploitation, habitat conversion, and introduced species have caused unprecedented extinctions and heavily degraded native bird populations in island ecosystems. In the Hawaiian Islands, stemming these losses has proven difficult as the highly specialized avifauna are often impacted – among other things – by poorly understood trophic disruptions as well as persistent climatic shifts. Here we investigate these dynamics by examining the trophic positions of 7 different taxa of producers and consumers across the last century in the subalpine māmane (Sophora chrysophylla) forest ecosystem on the island of Hawaiʻi. From museum collections and contemporary sampling, we analyzed the stable nitrogen (δ¹⁵N) values of producers and consumers to identify trophic and source amino acids and derive trophic enrichment constants specific to this food web. This enables us to reconstruct the diet of the palila (Loxioides bailleui), a critically endangered finch whose population recently declined 90 %. Our results show that from 1890 to 2006, the palila trophic position declined from 2.6 to 2.2, with cascading implications for its diet. Bayesian mixing model reconstructions indicate that palila trophic position changes likely arose from a 76 % decline (69.3 % to 16.6 % of diet) in the consumption of native moth caterpillars, and a 172 % increase (30.7 % to 83.4 %) in native plants. From the available ecosystem variables, exploratory Bayesian multiple regressions selected surface temperature changes, and the interactions of surface temperatures with drought and caterpillar parasitism as the primary drivers of these trophic changes. Despite the predicted increases of warming and drought, management interventions may build resiliency in this unique island ecosystem.