Through 2023.
Largely, this is a focus on career regular season value, due to time considerations. I'm doing this with the idea of a possible tournament, so I'm not just putting together the best 26 players, I'm trying to construct a roster. Every spot has a backup, 16 position players/10 pitchers. Making platoon considerations, each team has 2 dedicated closers, each bullpen has a lefty.
Starting Lineup v RH
C G.Hartnett
1B C.Anson
2B R.Sandberg
SS E.Banks
3B S.Hack (LH)
LF B.Williams (LH)
CF G.Gore (LH)
RF S.Sosa
DH M.Grace (LH)
Starting Lineup v. LH
C G.Hartnett
1B C.Anson
2B R.Sandberg
SS E.Banks
3B R.Santo
LF B.Williams (LH)
CF J.Ryan
RF S.Sosa
DH F.Chance
Reserves
2B J.Evers (LH)
2B B.Herman (RH)
SS J.Tinker
RF B.Nicholson (LH)
Who is the backup catcher? It's Chance, who caught a little less than 200 games with the Cubs; doing that allows for Billy Herman to make this roster, which is why there are 3 guys who can only play second base on this team - but Herman's got 40 career Cub WAR and given that the other best option is King Kelly as the backup catcher, this configuration best captures Cub history. There's a lot of 30+ WAR Cubs not here: Anthony Rizzo, Phil Cavaretta, Ed Williamson, Bill Dahlen, Hack Wilson. Wilson loses out to Gore to add Gore's left handed bat.
Starting Pitchers
F.Jenkins
R.Reuschel
M.Brown
B.Hutchison
G.Alexander
Bullpen
L.Smith
B.Sutter
C.Griffith
H.Vaughn (L)
J.Clarkson
Top four starters have 40+ Cub WAR in both b-ref and fangraphs; Smith and Sutter lead in saves and Vaughn is the top lefty. That left multiple guys for those last 3 spots, just left off are Maddux, Charlie Root, Bob Rush, Carlos Zambrano, Claude Passeau.