Outfielder Bryan Reynolds’ eight-year, $106.75 million contract became the largest in Pittsburgh Pirates history, far surpassing the eight-year, $70 million extension given to infielder Ke’Bryan Hayes in 2022.

Here’s a look at the largest contracts (total value) handed out by the Pirates:

1. Bryan Reynolds

Eight-year, $106.75 million extension in 2023

Read more: Pirates agree to 8-year, $106.75 million contract with star outfielder Bryan Reynolds

2. Ke’Bryan Hayes

Eight-year, $70 million extension in 2022

Read more: Pirates sign 3B Ke’Bryan Hayes to 8-year, $70 million deal as franchise cornerstone

3. Jason Kendall

Six-year, $60 million contract in 2000

4. Andrew McCutchen

Six-year, $51.5 million extension in 2012

5. Brian Giles

Six-year, $45 million extension in 2000

6. Francisco Liriano

Three-year, $39 million contract in 2014

7. Gregory Polanco

Five-year, $35 million extension in 2016

8. Francisco Cervelli

Three-year, $31 million extension in 2016

9. Starling Marte

Six-year, $31 million extension in 2014

10. Josh Harrison

Four-year, $27.3 million arbitration extension in 2015

Honorable mention

Kevin Young — four years, $24 million in 1999

Felipe Vazquez — four years, $22.5 million in 2018

Jack Wilson — three years, $20.2 million extension in 2006

Jason Bay — four years, $18.25 million in 2005

Jay Bell — four years, $17.5 million in 1993

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