This article describes the results of a study of briefs filed in the New York Court of Appeals between 1969 and 2008. In particular, portions of these briefs were analyzed using the Flesch Reading Ease test and the Flesh-Kincaid test. The first of these tests claims to determine how "readable" a piece of text might be, and the second expresses its results in terms of the grade level a hypothetical reader should have attained before the given text becomes "readable." Both of these tests are fallible, especially when used to determine the actual "readability" of a piece of text, but both provide a fixed point from which to compare different pieces of writing. And they are of particular interest to those interested in legal writing pedagogy because both tests measure aspects of Plain English such as the number of syllables in a word and the number of words in a sentence. The study's results will be disappointing to those who expect to see the influence of legal writing education reflected in the nature of practitioner writing. Far from showing an increase in Plain English use, the study records that legal writing in practice -- at least in New York State -- appears to have become significantly less plain since 1969. The study provides results for briefs filed in both civil and criminal matters and gives reading ease, grade level, average words per sentence, average sentences per paragraph, and incidence of passive voice scores for eight briefs each year between 1969 and 2008. In all but passive voice incidence, the results show a tendency for legal writing to become less "plain" over the years. The article suggests several possible reasons for the survey's results, and although the data do not point to a definite cause for the results, the article concludes that lawyer choice might be the most plausible explanation. Put simply, lawyers might not see any benefit to changing a practice style that has been considered acceptable in the past, even though judges, in particular, have been -- and remain -- highly critical of the quality of lawyer writing. Such criticisms, though, do not often obviously rise to the level of a judge changing the result of a case because of the poor quality of lawyer writing, and therefore lawyers likely see no benefit to the time-consuming and difficult task of changing their writing styles.