The Winter Meetings have started for baseball teams and naturally most of us wonder what the Pirates will do this offseason. Hahaha, I am kidding! We know they will do nothing. If I were Ben Cherington, here is what I would do.
First I would look at some of the non-tendered players, particularly Archie Bradley and David Dahl. I would try to sign them to two year deals with basically the understanding that if they do well this season, they will be traded to a contender.
Next, trade any useful pieces this offseason that teams may want. Joe Musgrove, Bryan Reynolds, Josh Bell. These guys will not be around for the next window, so move them now while they have some value.
Finally, I would try to convince to Ke’Bryan Hayes and Mitch Keller to sign team friendly deals that buy out their arbitration deals and possibly add a year or two. It would seem like the Pirates are interested in winning, but it would also make both players particularly valuable as trade candidates if they do emerge as superstars. Imagine if Keller turns into a top ten pitcher, the crazy offers that teams would make for someone like that who is under contract for a few more years.
I figure if they do that and finish in last place again, they should be able to have two very talented draft picks and as the young guys mature, they will be ready to compete. Once the window opens, this time they need to be ready and willing to keep the window open.
