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| Pos | Name | Age | 2020 | 2021 | 2022 | 2023 | 2024 | 2025 | 2026 | 2027 | 2028 | 2029 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| SP | Yu Darvish | 33 | $22.0m | $22.0m | $19.0m | $18.0m | ||||||
| CF | Jason Heyward | 30 | $21.0m | $21.0m | $22.0m | $22.0m | ||||||
| 3B | Kris Bryant | 28 | $18.6m | $19.5m(A) | ||||||||
| 1B | Anthony Rizzo | 30 | $16.5m | $16.5m(T) | ||||||||
| CL | Craig Kimbrel | 32 | $16.0m | $16.0m | $16.0m(T) | |||||||
| SP | Jon Lester | 36 | $15.0m(O) | $25.0m(T) | ||||||||
| SP | Tyler Chatwood | 30 | $13.0m | |||||||||
| SP | Kyle Hendricks | 30 | $12.0m | $14.0m | $14.0m | $14.0m | $16.0m(T) | |||||
| SP | Jose Quintana | 31 | $10.5m | |||||||||
| SS | Javier Baez | 27 | $10.0m | $12.1m(A) | ||||||||
| LF | Kyle Schwarber | 27 | $7.0m | $8.0m(A) | ||||||||
| C | Willson Contreras | 28 | $4.5m | $9.3m(A) | $12.1m(A) | |||||||
| 2B | Daniel Descalso | 33 | $2.5m | $3.5m(T) | ||||||||
| CF | Albert Almora Jr. | 26 | $1.6m | $1.8m(A) | $1.8m(A) | $1.8m(A#) | ||||||
| RF | Steven Souza Jr. | 31 | $1.0m | $1.1m(A#) | ||||||||
| RP | Kyle Ryan | 28 | $975k | |||||||||
| 2B | David Bote | 27 | $950k | $1.0m | $2.5m | $4.0m | $5.5m | $7.0m | $7.6m(T) | |||
| RP | Ryan Tepera | 32 | $900k | |||||||||
| RP | Jeremy Jeffress | 32 | $850k | |||||||||
| RP | Dan Winkler | 30 | $750k | $850k(A) | $900k(A) | |||||||
| SP | Jharel Cotton | 28 | $640k | $800k(A) | $800k(A) | $900k(A) | ||||||
| 2B | Ian Happ | 25 | $624k | $3.8m(A) | $6.0m(A) | $7.5m(A) | ||||||
| C | Victor Caratini | 26 | $592k | $4.4m(A) | $6.5m(A) | $8.5m(A) | ||||||
| CL | Rex Brothers | 32 | $564k(*) | $900k(A) | $1.1m(A#) | |||||||
| 2B | Robel Garcia | 27 | $564k(*) | $564k(auto) | $564k(auto) | $750k(A*) | $750k(A) | $750k(A) | $900k(A) | |||
| RP | Zac Grotz | 27 | $564k | $564k(auto) | $850k(A*) | $850k(A) | $850k(A) | $900k(A) | ||||
| LF | Matt Joyce | 35 | $564k | |||||||||
| 2B | Jason Kipnis | 33 | $564k | |||||||||
| 3B | Vimael Machin | 26 | $564k(*) | $564k(auto) | $564k(auto) | $750k(A*) | $750k(A) | $750k(A) | $900k(A) | |||
| RF | Nick Markakis | 36 | $564k | |||||||||
| RP | Trevor Megill | 26 | $564k | $564k(auto) | $800k(A*) | $800k(A) | $800k(A) | $800k(A) | ||||
| LF | Ian Miller | 28 | $564k(*) | $564k(auto) | $564k(auto) | $850k(A*) | $850k(A) | $850k(A) | $900k(A) | |||
| RP | Alec Mills | 28 | $564k | $564k(auto) | $850k(A*) | $850k(A) | $850k(A) | $900k(A) | ||||
| RP | Brandon Morrow | 35 | $564k | |||||||||
| RP | James Norwood | 26 | $564k | $564k(auto) | $564k(auto) | $750k(A*) | $750k(A) | $750k(A) | $900k(A) | |||
| RF | Jordan Patterson | 28 | $564k(*) | $564k(auto) | $564k(auto) | $850k(A*) | $850k(A) | $850k(A) | $900k(A) | |||
| 2B | Hernan Perez | 29 | $564k | |||||||||
| RP | Casey Sadler | 30 | $564k | $564k(auto) | $850k(A) | $850k(A) | $850k(A) | |||||
| CL | Rowan Wick | 27 | $564k(*) | $564k(auto) | $750k(A*) | $750k(A*) | $750k(A) | $900k(A) | $1.1m(A#) | |||
| RP | Brad Wieck | 28 | $564k | $564k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | ||||
| TOTAL | $187.0m | $187.8m | $110.5m | $85.6m | $30.4m | $15.3m | $13.2m | $0 | $0 | $0 |
