We introduce a dataset for studying the evolution of words, constructed from WordNet and the Google Books Ngram Corpus. The dataset tracks the evolution of 4,000 synonym sets (synsets), containing 9,000 English words, from 1800 AD to 2000 AD. We present a supervised learning algorithm that is able to predict the future leader of a synset: the word in the synset that will have the highest frequency. The algorithm uses features based on a word’s length, the characters in the word, and the historical frequencies of the word. It can predict change of leadership (including the identity of the new leader) fifty years in the future, with an F-score considerably above random guessing. Analysis of the learned models provides insight into the causes of change in the leader of a synset. The algorithm confirms observations linguists have made, such as the trend to replace the -ise suffix with -ize, the rivalry between the -ity and -ness suffixes, and the struggle between economy (shorter words ar)