The problem is this. Right now the Cubs do not have much room for error on landing who they need to land. If they wait until January that margin for error is even smaller. With each free agent that comes off the board, their job becomes harder and harder. Even if the Cubs weren't targeting that particular free agent, that's one less target for other teams who were targeting that free agent and now they potentially pivot to a target the Cubs are in on. So yes, things could still work out alright, but with each passing day with each free agent agreement it becomes less and less likely