All Time Cubs Roster

 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.