Assuming starting point after arbitration is 206M and 246M is the point at which draft picks start being penalized, I'd do the following. Trade Almora+Chatwood for salary relief (-13M in 2019) Trade Caratini+Kintzler for salary relief (-5.5M) Trade Happ+Montomery+Hatch to Colorado for J.Gray (0, 3 years left) Trade Duensing +1M to ARI for Jarrod Dyson (+1M, one year left on Dyson) Trade Monasterio+Little to SF for W.Smith(+3.5M, only one year left under contract)) Sign Harper for 10/300 (+30M) Sign R.Rivera for 1/2.5M (+2.5M) Sign Z.Britton 3/36M (+12M) Let Rangers buyout Hamels' option (0M) C:Contreras 1B:Rizzo 2B:Zobrist SS:Baez 3B:Bryant LF:Schwarber CF:Heyward RF:Harper Bench:Bote,Lastella,Rivera,Dyson SP:Lester,Hendricks,Darvish,Gray,Quintana RP:Britton,Morrow,Strop,Edwards,Cishek,Smyly,Smith Gives the Cubs a bullpen of death, another SP with huge upside who's also young, another impact bat, but they certainly do lose depth. This also leaves just under 10M to make any other moves. I don't think Jose Iglesias is the worst option.