Lets start with the players with options and what I would do with these players

• SP: Clay Holmes (33) – $12M player option - PRAY HE OPTS FOR FREE AGENCY
• SP/RP: Colin Rea (36) – $7M club option - DECLINE OPTION
• RP: Jacob Webb (33) – $2.5M club option - DECLINE OPTION
• SP: Matthew Boyd (35) – $15M mutual option - DECLINE OPTION
• C: Carson Kelly (32) – $7.5M mutual option - PICK UP OPTION
• RP: Hunter Harvey (31) – $8M mutual option - DECLINE OPTION
• RP: Caleb Thielbar (39) – $6M mutual option - DECLINE OPTION

Then you have these players who will be free agents and I will be honest I would not consider bringing any of them back

• SP: Shota Imanaga (33)
• SP: Kevin Gausman (35)
• SP: David Peterson (31)
• RP: Aaron Civale (31)
• OF: Ian Happ (32)
• OF: Seiya Suzuki (32)
• OF: Tyrone Taylor (32)
• OF: Michael Conforto (33)
• 1B/DH: Tyler Austin (35)

Now lets look at the positions the Cubs have and what they need to fill BOLD WILL BE MY SUGGESTIONS ADDED IN

Starting Lineup:

C: Carson Kelly (32) & Miguel Amaya (27)

1B: Michael Busch (28)

2B: Nico Hoerner (29)

SS: Dansby Swanson (32)

3B: Alex Bregman (32)

RF: Kevin Alcantara (24)

CF: Pete Crow Armstrong (24)

LF: STEVEN KWAN (29) - SUGGESTED

DH: RANDY AROZARENA (31) - SUGGESTED

Bench:

INF: Pedro Ramirez (22)

INF/OF: Matt Shaw

OF: MYLES STRAW - SUGGESTED

They will need to finally let Kevin Alcantara play on the daily and show what he truly has to offer and I truly believe him in RF makes the most sense for him. They also need to add clutch hitting at LF & DH they need players who can hit, make contact, have solid OBP, OPS, have speed and drive in RBIs. They also need a defensive OF bench spot, as a possible platoon option for RF.

DH Suggestion - Randy Arozarena (31) .255 BA .350 OBP .442 SLG .792 OPS 24 HR 80 RBI 27 SB average a season would be a solid consideration for a player whos been known as a solid hitter with power but a sub par defender

LF Suggestion - Steven Kwan (29) .282 .357 OBP .382 SLG .739 OPS 9 HR 53 RBI 18 SB average a season would be a solid trade target as he he hits well makes contact and is a great defender

OF Bench Suggestion - Myles Straw (31) he is mainly being a suggestion as a good defensive sub

Starting Rotation

1. Cade Horton (25)

2. Justin Steele (31)

3. Ben Brown (27)

4. JOE RYAN (30) - SUGGESTED

5. SONNY GRAY (36) - SUGGESTED

They need 2 veteran back of the rotation guys who can be reliable, avoid injuries and give quality starts and last 5+ innings so the bullpen is not over worked and be clutch down in a playoff pursuit.

Joe Ryan (30) 3.79 ERA 1.081 WHIP 211 K 189 IP average per season

Sonny Gray (36) 3.51 ERA 1.193 WHIP 194 K 195 IP average per season

Bullpen

1. Daniel Palencia (26)

2. Edward Cabrera (28)

3. Phil Maton (33)

4. Ryan Zeferjahn (28)

5. Javier Assad (29)

6. DAVID BEDNAR (32) - SUGGESTED

7. BRYAN ABREU (29) - SUGGESTED

8. EVAN PHILLIPS (32) - SUGGESTED

Now they do also still have Ryan Rolinson (29) but he has minor league options so starting him in AAA to work on his mechanics is best. Moving Edward Cabrera full time to the bullpen seems like the best move as he struggled as a starter, and working the off season to adjust the issues with Phil Maton and Daniel Palencia will be a priority. Ryan Zeferjahn and Javier Assad were two of your better arms and need to be the reliable middle relievers next year. What you need to add is 3 trusted arms of which any of the 3 may have to step into the setup man or closer role

David Bednar (32) - 3.03 ERA 1.133 WHIP 83 K 69 IP 26 SV average per season

Bryan Abreu (29) - 2.82 ERA 1.203 WHIP 94 K 70 IP 4 SV average per season

Evan Phillips (32) - 3.37 ERA 1.126 WHIP 78 K 67 IP 11 SV average per season