I'm operating with the assumption the Cubs have $32 million to work with this offseason. Offseason plan: I listed rationale in the spoiler tags. Don't bring in Joe Girardi. I can buy in with basically anyone else that's been brought up (Ross, Beltran, Espada, Fuld, Bard, Loretta). I think it'll be Ross, but my pick would be Espada. Poach the absolute best pitching and hitting specialists from the Rays, Astros, Dodgers and give them Assist GM/Director positions. Trades: Willson Contreras, Jose Quintana, James Norwood for Drew Waters, Kyle Wright, Ender Inciarte Ian Happ, David Bote, Duane Underwood Jr. (or Alzolay if needed) for Jon Gray Free Agents: Sign Yasmani Grandal 3 year/$50 million Howie Kendrick 2 year/$15 million Billy Hamilton 1 year/$2.5 million (25/26th player) Sign Dellin Betances 1 year/$2.5 million Pedro Strop 1 year $2.5 million Total payroll add is approximately $30 million Pitching staff: SP) Hendricks SP) Darvish SP) Gray SP) Lester SP) Wright/Graveman/MIlls RP) Kimbrel RP) Betances RP) Wick RP) Strop RP) Wieck RP) Chatwood RP) Kyle Ryan RP) Graveman/Mills/Triple AAA filler Position Players: 2B) Hoerner/Kendrick 3B) Bryant 1B) Rizzo SS) Baez C) Grandal LF) Schwarber CF) Inciarte RF) Heyward B) Caratini B) Hoerner/Kendrick B) Kemp B) Descalso B) Almora B) Hamilton