If the Cubs cannot reach a contract extension agreement with Rizzo, what do they care where they trade him? They take the best offer be it Milwaukee or anywhere else and move on. The alternative is they watch him play out the string on a second rate team then leave as a free agent or trade him a somewhere for less desirable talent. Realistically if the Cubs shop Rizzo, they are probably going to get several decent offers that are all pretty close. In a video game you would just take the best offer even if it was from the Brewers, but the real life implications matter. Imagine the backlash from local media, casual fans and season tickets holders if the Brewers had traded Braun in '15 to the Cubs or Cardinals. It's not really worth that kind of headache for the team if all the offers are kind of close anyway, and it's not worth it for the Brewers to offer something head and shoulders above everyone else for a 2 month rental. 1. The Brewers are not the Cubs rival. The Cardinals are the Cubs rival. Also no one is going to care about where someone plays for two months in a dead season. If Braun was traded in 15 it would have been a one day story until the battle for the #6 wide receiver in training camp supplanted it. Similarly the White Sox are likely playoff bound and the Bears have a new QB who will definitely make things work this time. 2. The bigger issue for the Cubs is that unless the Cubs send along salary, no one they have to trade has that much value. Rizzo and Schoop have the same offensive output and one costs $4.5M this season and the other $16.5M.