Many neurological disorders, especially those that result in dementia, impact speech and language production. A number of studies have shown that there exist subtle changes in linguistic complexity in these individuals that precede disease onset. However, these studies are conducted on controlled speech samples from a specific task. This thesis explores the possibility of using natural language processing in order to detect declining linguistic complexity from more natural discourse. We use existing data from public figures suspected (or at risk) of suffering from cognitive-linguistic decline, downloaded from the Internet, to detect changes in linguistic complexity. In particular, we focus on two case studies. The first case study analyzes President Ronald Reagan’s transcribed spontaneous speech samples during his presidency. President Reagan was diagnosed with Alzheimer’s disease in 1994, however my results showed declining linguistic complexity during the span of the 8 years he was in office. President George Herbert Walker Bush, who has no known diagnosis of Alzheimer’s disease, shows no decline in the same measures. In the second case study, we analyze transcribed spontaneous speech samples from the news conferences of 10 current NFL players and 18 non-player personnel since 2007. The non-player personnel have never played professional football. Longitudinal analysis of linguistic complexity showed contrasting patterns in the two groups. The majority (6 of 10) of current players showed decline in at least one measure of linguistic complexity over time. In contrast, the majority (11 out of 18) of non-player personnel showed an increase in at least one linguistic complexity measure.