Description : I wrote this critical essay after I got my Master’s Degree in English and went to a Thomas Wolfe festival in 1991. While I was there, I had the good fortune to run into his nephew, who was the only living relative who actually knew him. I’ve always been a sucker for a good love story and was pleased to discover the best one in American Literature, in my humble opinion, in Wolfe’s long novel, The Web and The Rock. In that thinly-veiled self-portrait, Wolfe loves and captures the spirit of Aline Bernstein. In his extravagant rhetoric, he immortalizes her in his fictional character, Esther Jack. Written in the 1930’s, it shows a remarkable respect for an independent woman, and in this respect, Wolfe was ahead of his time. The fact that Aline won a Tony award for Best Costume Design, makes the story of her relationship with Wolfe even more fascinating.