The Oakland A's have 36-year-old Rajai Davis manning CF, 32-year-old Matt Joyce in RF, and nothing for OF prospects. They have Sonny Gray, only 27 years old and arby-eligible next year, along with bullpen pieces Madson, Casilla, and Doolittle to deal. Brewers are loaded with OF prospects - Brinson, Phillips, Cordell, Ray, Clark, Harrison (and 24-year-old Santana). Not all will develop, and if they all do, there won't be room for all of them. They will have to deal some of them eventually. Ray, Cordell, Orimoloye, two lower-level pitchers (Diplan? Peralta? Bickfod? Medeiros? Supak?), throw in Wily Peralta (plus some cash to pay his salary) for a change-of-scenery as well as Wilkerson, for Gray, Madson, and Doolittle. Buy out Gray's two arby years and sign him to a 5-year deal through age 32/33. Using MLB.com's prospect rankings, that's the Brewers #2 (Ray), #11 (Diplan), #12 (Bickford), #16 (Cordell), and #24 (Orimoloye) plus Wily Peralta and Wilkerson. I don't think it will be expensive to acquire them as Gray will likely get eight figures in arby, and Madson and Doolittle combine for over $11M in salary next year. Madison is pitching well, but at 36 and making $7.6M/year you don't have to give up a lot to get him. Doolittle is effective against both lefties and righties and has team options in 2019 and 2020 (at $6M and $6.5M), so they could have him for up to four years. You aren't mortgaging the future for this year because you'd have Gray for five years, Doolittle for up to four years, and Madson is signed through next season - they could trade any of those guys in the offseason and still stick to "the plan". There won't be room for all seven of those OFs; they have to trade some of them eventually. You keep the big 4 pitching prospects (Hader, Woodruff, Ortiz, Burnes) plus Brinson. Future is still bright, still sticking to the plan.