In the summer of 2016, Jack hired a painter to create portraits of famous people. Jack's business idea was to have famous people contractually agree to have their portraits done, and to have those portraits hang in a gallery. Jack would then market and sell prints of the portraits, which would also contain a handprint of the famous person at the bottom of the portrait. And, Jack would pay the famous person an upfront fee, as well as split with the famous person the proceeds from the sale of the prints of the portraits.

The first famous person Jack met with was Hillary Clinton. After Jack and Clinton drank a considerable amount of wine, Clinton orally agreed that Clinton authorized the painting and would provide a handprint on the portrait. Without the cash to pay Clinton the upfront fee, Jack orally agreed that he would deed to her some real property he owned in upstate New York.

After Clinton lost her presidential bid on November 8, 2016, Clinton informed Jack that she did not want to go into business with him or have anything to do with his business idea. Forging ahead anyway, Jack arranged to have his painter do Clinton's portrait. Jack incurred significant expense in marketing the yet to be painted portrait and in making a down payment to a company that would have the prints made once Clinton placed her handprint on the painting. Jack had the portrait delivered to Clinton's home in New York so that Clinton could make the handprint. Clinton kept the portrait, refused to put her handprint on the painting or return the painting to Jack. Clinton claimed that the oral agreement was unenforceable. Jack then filed a lawsuit against Clinton.

What will Jack argue? What will Clinton argue? How will the court rule on this case?