How important are essays?

Most teams need more than two recruits each year. From what I understand, Chicago is a true crap shoot after the first two recruits. In other words, a coach’s list could well be 25-30 recruits long, with the top two receiving likely letters, and the coach hoping to get another handful from the list of 25-30 admitted. There is not a lot of security unless you have received the likely letter. Your best bet would be to talk to the coach about where you stand.