If you only lost $1600 last year, I would say you did fairly well. Are there any tax benefits to be gained by claiming a loss on ticket sales? Is there any way to write those losses off? I'm sure that is a majority of people right now, but if the Cubs are good in 2 years tickets could quickly become a money-making proposition again. Remember how few people were giving up their tickets just a few short years ago? If the Cubs become a consistent contender, someone buried 50,000+ spots deep on the waiting list may have to wait many years before getting the chance to buy tickets.