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| Pos | Name | Age | 2019 | 2020 | 2021 | 2022 | 2023 | 2024 | 2025 | 2026 | 2027 | 2028 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| SP | Tyler Glasnow | 26 | $28.6m | $28.6m | $28.6m | $28.6m | $28.6m(O) | $28.6m | $28.6m | $28.6m(P) | ||
| 3B | Kyle Seager | 31 | $19.0m | $19.0m | $18.0m | $15.0m(T) | ||||||
| C | Yasmani Grandal | 30 | $18.0m | $20.0m | $22.0m | $23.0m(P) | ||||||
| 2B | Dustin Pedroia | 36 | $15.0m | $13.0m | $12.0m | |||||||
| 1B | Anthony Rizzo | 30 | $11.0m | $14.5m(T) | $14.5m(T) | |||||||
| SS | Jose Iglesias | 29 | $8.5m | $8.5m | $8.5m | |||||||
| SP | Jake Odorizzi | 29 | $7.7m | $8.7m | $8.7m | $9.7m | ||||||
| LF | Kyle Schwarber | 26 | $6.9m | $8.0m(A) | $9.5m(A) | |||||||
| RP | Luke Gregerson | 35 | $5.0m | $5.0m(T) | ||||||||
| RF | Carlos Gonzalez | 34 | $3.8m | |||||||||
| RP | Tony Watson | 34 | $3.5m | $2.5m(P) | ||||||||
| RP | Brad Boxberger | 31 | $2.8m | |||||||||
| C | Miguel Montero | 36 | $1.7m | |||||||||
| SS | Tim Anderson | 26 | $1.4m | $4.0m | $7.3m | $9.5m | $12.5m | $14.0m | ||||
| SP | Elieser Hernandez | 24 | $1.1m | $1.1m(auto) | $1.1m(auto) | $1.2m(A*) | $1.2m(A) | $1.2m(A) | $1.2m(A) | |||
| SP | Anthony DeSclafani | 29 | $950k | $3.8m(A) | $5.0m(A) | |||||||
| RP | Chris Devenski | 28 | $893k | $1.1m(A) | $1.1m(A) | |||||||
| RP | Ryan Tepera | 31 | $850k | $950k(A) | $950k(A) | |||||||
| SP | Ryan Borucki | 25 | $818k | $818k(auto) | $818k(auto) | $900k(A*) | $900k(A) | $900k(A) | $900k(A) | |||
| CF | Tyler Naquin | 28 | $565k | $850k(A) | $850k(A) | $850k(A) | ||||||
| CL | Diego Castillo | 25 | $555k | $555k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | ||||
| SP | Jalen Beeks | 26 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| SP | Joe Biagini | 29 | $545k(*) | $545k(auto) | $850k(A) | $850k(A) | $850k(A) | |||||
| CL | Cody Carroll | 27 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| 1B | Hunter Dozier | 28 | $545k | $545k(auto) | $700k(A*) | $700k(A) | $700k(A) | $700k(A) | ||||
| RP | Derian Gonzalez | 24 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| RP | Conner Greene | 24 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| CL | Luke Leftwich | 25 | $545k | $545k(auto) | $850k(A*) | $850k(A) | $1.1m(A) | $1.4m(A) | ||||
| SP | Pablo Lopez | 23 | $545k | $545k(auto) | $4.0m(A*) | $4.4m(A) | $7.0m(A) | $9.0m(A) | ||||
| 2B | Yairo Munoz | 24 | $545k | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | ||||
| RF | Daniel Palka | 28 | $545k | $545k(auto) | $800k(A*) | $800k(A) | $800k(A) | $900k(A) | ||||
| SP | Freicer Perez | 23 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| RP | Carlos Alejandro Ramirez | 28 | $545k | $545k(auto) | $1.3m(A*) | $1.4m(A) | $2.0m(A) | $2.7m(A) | ||||
| LF | Joey Rickard | 28 | $545k(*) | $545k(auto) | $850k(A) | $850k(A) | $850k(A) | |||||
| SP | Antonio Santillan | 22 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| LF | Austin Slater | 26 | $545k | $545k(auto) | $700k(A*) | $700k(A) | $700k(A) | $900k(A) | ||||
| SP | Caleb Smith | 28 | $545k | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | ||||
| RP | Jose Torres | 26 | $545k(*) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | ||||
| SP | Trevor Williams | 27 | $545k(*) | $545k(auto) | $850k(A) | $850k(A) | $850k(A) | |||||
| SP | Jordan Yamamoto | 23 | $545k(*) | $545k(auto) | $545k(auto) | $850k(A*) | $850k(A) | $850k(A) | $850k(A) | |||
| TOTAL | $148.9m | $151.3m | $156.9m | $109.4m | $67.4m | $69.7m | $36.6m | $28.6m | $0 | $0 |
