Born Jul 14, 1974 · Meriden, NH · age 52
Built the Boston Red Sox's 2013 World Series champion as general manager before taking on a long-term, development-first rebuild of the Pittsburgh Pirates.
12 seasons with salary-era data across 3 stints. All figures are franchise-level outcomes during the tenure, not solely attributable to one executive.
| Team | Role | Years | Szns | WAB | WAB/yr | TAB | WAR surp | HG | Trade | FA | R5 | AcqLev | W-L% | PO | Pen | WS | Surp $M |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| ▸ Pirates | GM | 2020–present | 5 | -11.4 | -2.29 | -22.5 | +18.4 | +36.9 | +10.1 | -20.3 | -0.1 | 1.36 | 0.429 | – | – | – | +99 |
| ▸ Red Sox | GM | 2012–2015 | 4 | -31.7 | -7.91 | -19.4 | -86.9 | +33.0 | +8.3 | +27.6 | +0.0 | 2.86 | 0.486 | 1 | 1 | 1 | -247 |
| ▸ Red Sox | GM | 2006–2006 | 1 | -2.1 | -2.05 | -10.5 | -32.5 | +3.3 | -0.3 | -21.1 | +0.0 | 0.45 | 0.531 | – | – | – | -65 |
| Career total (1985+ data) | 12 | -45.1 | -52.4 | -101.0 | +73.2 | +18.0 | -13.8 | -0.1 | 1.88 | 0.459 | 1 | 1 | 1 | -212 | |||
Acquired minus surrendered / signed minus walked.
Every roster slot ranked best→worst by WAR, averaged across Ben Cherington's seasons. Bars = his rosters; the black line = the league-average player at each slot. Staying above the line deep into the roster is the depth edge.
| Player | Pos | Team | How | Year | Szns | fWAR | WAR/yr | Lev |
|---|---|---|---|---|---|---|---|---|
| Rafael Devers | 3B | BOS | Intl FA | 2013 | 9 | +25.8 | +2.9 | – |
| Josh Beckett | P | BOS | Trade | 2006 | 7 | +21.5 | +3.1 | 0.5 |
| Eduardo Rodríguez | P | BOS | Trade | 2014 | 6 | +14.3 | +2.4 | – |
| Paul Skenes | P | PIT | Draft | 2024 | 3 | +14.0 | +4.7 | – |
| Rick Porcello | P | BOS | Trade | 2014 | 5 | +13.1 | +2.6 | 2.9 |
| David Price | P | BOS | Free agency | 2015 | 4 | +10.7 | +2.7 | 22.9 |
| Mike Lowell | 3B | BOS | Trade | 2006 | 3 | +8.7 | +2.9 | 1.1 |
| Andrew Benintendi | OF | BOS | Draft | 2015 | 4 | +7.9 | +2.0 | – |
| Brock Holt | 2B/3B/OF | BOS | Trade | 2012 | 5 | +7.1 | +1.4 | 1.4 |
| Coco Crisp | OF | BOS | Trade | 2006 | 3 | +6.9 | +2.3 | 0.4 |
| Koji Uehara | P | BOS | Free agency | 2012 | 4 | +6.1 | +1.5 | 13.8 |
| Craig Kimbrel | P | BOS | Trade | 2015 | 3 | +5.8 | +1.9 | 6.2 |
| Mike Napoli | C/1B | BOS | Free agency | 2013 | 2 | +5.5 | +2.7 | 15.3 |
| Shane Victorino | OF | BOS | Free agency | 2012 | 3 | +4.9 | +1.6 | 22.3 |
| David Bednar | P | PIT | Trade | 2021 | 4 | +4.7 | +1.2 | 0.0 |
| Braxton Ashcraft | P | PIT | Draft | 2025 | 2 | +4.4 | +2.2 | – |
| Nick Gonzales | 2B | PIT | Draft | 2023 | 3 | +4.1 | +1.4 | – |
| Carmen Mlodzinski | P | PIT | Draft | 2023 | 4 | +3.8 | +1.0 | – |
| Stephen Drew | SS | BOS | Free agency | 2012 | 2 | +3.6 | +1.8 | 16.6 |
| Jared Triolo | 3B/SS | PIT | Draft | 2023 | 4 | +3.5 | +0.9 | – |
| Spencer Horwitz | 1B | PIT | Trade | 2024 | 2 | +3.1 | +1.5 | 0.5 |
| Joe Kelly | P | BOS | Trade | 2014 | 5 | +3.0 | +0.6 | 0.1 |
| Wade Miley | P | BOS | Trade | 2014 | 1 | +2.7 | +2.7 | 4.5 |
| Cody Ross | OF | BOS | Free agency | 2012 | 1 | +2.7 | +2.7 | 1.3 |
| Brandon Lowe | 2B | PIT | Trade | 2025 | 1 | +2.7 | +2.7 | 23.7 |
| Joey Bart | C | PIT | Trade | 2024 | 3 | +2.7 | +0.9 | 0.1 |
| Daniel Bard | P | BOS | Draft | 2006 | 3 | +2.6 | +0.9 | – |
| Jared Jones | P | PIT | Draft | 2024 | 2 | +2.5 | +1.2 | – |
| Steven Wright | P | BOS | Trade | 2012 | 4 | +2.3 | +0.6 | – |
| Jose Quintana | P | PIT | Trade | 2022 | 1 | +2.1 | +2.1 | 0.1 |
| Johan Oviedo | P | PIT | Trade | 2022 | 3 | +2.0 | +0.7 | 0.0 |
| Jack Suwinski | OF | PIT | Draft | 2022 | 2 | +2.0 | +1.0 | – |
| Andrew Miller | P | BOS | Trade | 2012 | 3 | +2.0 | +0.7 | 0.3 |
| Dennis Santana | P | PIT | Trade | 2024 | 2 | +2.0 | +1.0 | 0.1 |
| Bubba Chandler | P | PIT | Draft | 2025 | 2 | +1.9 | +1.0 | – |
| Josh Reddick | OF | BOS | Draft | 2006 | 2 | +1.8 | +0.9 | – |
| Bailey Falter | P | PIT | Trade | 2023 | 2 | +1.7 | +0.8 | 0.1 |
| Álex González | SS | BOS | Free agency | 2006 | 2 | +1.6 | +0.8 | 0.7 |
| Jonny Gomes | DH/OF | BOS | Free agency | 2012 | 2 | +1.5 | +0.8 | 6.4 |
| Jason Delay | C | PIT | Draft | 2022 | 3 | +1.3 | +0.4 | – |
| Yasmani Grandal | C | PIT | Free agency | 2024 | 1 | +1.3 | +1.3 | 0.1 |
| Tyler Anderson | P | PIT | Trade | 2021 | 1 | +1.3 | +1.3 | 0.0 |
| Mike Burrows | P | PIT | Draft | 2024 | 1 | +1.2 | +1.2 | – |
| Konnor Griffin | SS | PIT | Draft | 2026 | 1 | +1.2 | +1.2 | – |
| Dauri Moreta | P | PIT | Trade | 2022 | 2 | +1.2 | +0.6 | 0.2 |
| Ryan O'Hearn | 1B | PIT | Free agency | 2026 | 1 | +1.2 | +1.2 | 10.3 |
| Jake Mangum | OF | PIT | Trade | 2026 | 1 | +1.2 | +1.2 | 10.6 |
| Aroldis Chapman | P | PIT | Free agency | 2024 | 1 | +1.1 | +1.1 | 0.1 |
| Roansy Contreras | P | PIT | Trade | 2021 | 3 | +1.1 | +0.4 | – |
| Jake Peavy | P | BOS | Trade | 2013 | 2 | +1.1 | +0.6 | 4.2 |
| Mike Carp | 1B/OF | BOS | Trade | 2013 | 1 | +1.1 | +1.1 | 5.9 |
| Rich Hill | P | PIT | Trade | 2023 | 1 | +1.1 | +1.1 | 0.2 |
| Alejandro De Aza | OF | BOS | Trade | 2015 | 1 | +1.0 | +1.0 | 1.8 |
| Robbie Ross | P | BOS | Trade | 2015 | 3 | +1.0 | +0.3 | 0.2 |
| Alex Cora | 2B/SS | BOS | Free agency | 2006 | 3 | +0.9 | +0.3 | 1.0 |
| Julián Tavárez | P | BOS | Free agency | 2006 | 1 | +0.9 | +0.9 | 5.0 |
| Rusney Castillo | OF | BOS | Intl FA | 2014 | 2 | +0.9 | +0.5 | – |
| Pedro Ciriaco | 3B/SS | BOS | Free agency | 2012 | 1 | +0.9 | +0.9 | 0.5 |
| Luis Ortiz | P | PIT | Draft | 2022 | 2 | +0.9 | +0.4 | – |
| Yoenis Céspedes | OF | BOS | Trade | 2014 | 1 | +0.9 | +0.9 | 0.6 |
| Austin Hedges | C | PIT | Trade | 2023 | 1 | +0.9 | +0.9 | 0.2 |
| Isaac Mattson | P | PIT | Free agency | 2023 | 3 | +0.8 | +0.3 | 0.0 |
| Mason Montgomery | P | PIT | Trade | 2025 | 1 | +0.8 | +0.8 | 6.8 |
| Endy Rodríguez | C | PIT | Draft | 2023 | 2 | +0.8 | +0.4 | – |
| Carlos Santana | 1B | PIT | Trade | 2023 | 1 | +0.8 | +0.8 | 0.1 |
| Duane Underwood | P | PIT | Trade | 2021 | 2 | +0.8 | +0.4 | 0.0 |
| Isiah Kiner-Falefa | SS | PIT | Trade | 2024 | 2 | +0.8 | +0.4 | 0.0 |
| Evan Sisk | P | PIT | Trade | 2025 | 2 | +0.8 | +0.4 | 0.0 |
| Julio Lugo | SS | BOS | Free agency | 2006 | 2 | +0.7 | +0.4 | 2.1 |
| Heath Hembree | P | BOS | Trade | 2014 | 5 | +0.7 | +0.1 | 1.8 |
| Chris Young | OF | BOS | Free agency | 2015 | 1 | +0.7 | +0.7 | 5.0 |
| Osvaldo Bido | P | PIT | Draft | 2023 | 1 | +0.7 | +0.7 | – |
| Hunter Stratton | P | PIT | Draft | 2023 | 2 | +0.7 | +0.3 | – |
| Vince Velasquez | P | PIT | Free agency | 2022 | 1 | +0.7 | +0.7 | 0.1 |
| Ryan Sweeney | OF | BOS | Trade | 2012 | 1 | +0.7 | +0.7 | 0.4 |
| Burke Badenhop | P | BOS | Trade | 2014 | 1 | +0.7 | +0.7 | 0.4 |
| Caleb Ferguson | P | PIT | Trade | 2025 | 1 | +0.7 | +0.7 | 0.2 |
| Ryan Borucki | P | PIT | Free agency | 2023 | 1 | +0.6 | +0.6 | 0.1 |
| Roberto Pérez | C | PIT | Free agency | 2021 | 1 | +0.6 | +0.6 | 0.0 |
| Brendan Donnelly | P | BOS | Trade | 2006 | 1 | +0.5 | +0.5 | 2.9 |
| Ryan Dempster | P | BOS | Free agency | 2012 | 1 | +0.5 | +0.5 | 1.9 |
| Brian Johnson | P | BOS | Draft | 2012 | 3 | +0.5 | +0.2 | – |
| Trevor Cahill | P | PIT | Free agency | 2021 | 1 | +0.5 | +0.5 | 0.0 |
| Ángel Perdomo | P | PIT | Free agency | 2023 | 1 | +0.5 | +0.5 | 0.1 |
| Gregory Soto | P | PIT | Free agency | 2025 | 1 | +0.5 | +0.5 | 4.0 |
| Mark Loretta | 2B | BOS | Trade | 2006 | 1 | +0.5 | +0.5 | 0.2 |
| Tyler Heineman | C | PIT | Trade | 2022 | 1 | +0.5 | +0.5 | 0.0 |
| Colin Holderman | P | PIT | Trade | 2023 | 2 | +0.5 | +0.3 | 0.2 |
| Quintin Berry | OF | BOS | Trade | 2013 | 1 | +0.4 | +0.4 | 1.6 |
| Jake Marisnick | OF | PIT | Free agency | 2022 | 1 | +0.4 | +0.4 | 0.0 |
| Yohan Ramírez | P | PIT | Free agency | 2024 | 3 | +0.4 | +0.1 | 0.0 |
| Michael Taylor | OF | PIT | Free agency | 2024 | 1 | +0.4 | +0.4 | 0.0 |
| Wily Mo Peña | OF | BOS | Trade | 2006 | 1 | +0.4 | +0.4 | 0.4 |
| Dillon Peters | P | PIT | Trade | 2021 | 1 | +0.4 | +0.4 | 0.0 |
| Dan Vogelbach | 1B/DH | PIT | Trade | 2022 | 1 | +0.4 | +0.4 | 0.0 |
| Andre Jackson | P | PIT | Trade | 2023 | 1 | +0.4 | +0.4 | 0.1 |
| Joey Wentz | P | PIT | Trade | 2024 | 2 | +0.4 | +0.2 | 0.0 |
| Craig Breslow | P | BOS | Free agency | 2006 | 3 | +0.3 | +0.1 | 0.1 |
| Travis Lakins | P | BOS | Draft | 2015 | 1 | +0.3 | +0.3 | – |
| Tommy Layne | P | BOS | Free agency | 2013 | 3 | +0.3 | +0.1 | 0.1 |
| Austin Maddox | P | BOS | Draft | 2012 | 1 | +0.3 | +0.3 | – |
| Scott Podsednik | OF | BOS | Free agency | 2012 | 1 | +0.3 | +0.3 | 0.2 |
| Carl Crawford | OF | BOS | Trade | 2012 | 1 | +0.3 | +0.3 | 0.2 |
| Jemile Weeks | 2B | BOS | Trade | 2014 | 2 | +0.3 | +0.2 | 0.2 |
| Martín Pérez | P | PIT | Trade | 2024 | 1 | +0.3 | +0.3 | 0.0 |
| Nick Tropeano | P | PIT | Trade | 2020 | 1 | +0.3 | +0.3 | 0.1 |
| Joshua Palacios | OF | PIT | Trade | 2023 | 2 | +0.3 | +0.2 | 0.0 |
| Jalen Beeks | P | PIT | Trade | 2024 | 1 | +0.3 | +0.3 | 0.0 |
| Justin Lawrence | P | PIT | Trade | 2025 | 1 | +0.3 | +0.3 | 0.1 |
| Rubby De La Rosa | P | BOS | Trade | 2012 | 1 | +0.2 | +0.2 | 0.2 |
| Edward Mujica | P | BOS | Free agency | 2013 | 1 | +0.2 | +0.2 | 0.1 |
| Vicente Padilla | P | BOS | Free agency | 2012 | 1 | +0.2 | +0.2 | 0.1 |
| Bobby Poyner | P | BOS | Draft | 2015 | 1 | +0.2 | +0.2 | – |
| Yerry De los Santos | P | PIT | Draft | 2022 | 2 | +0.2 | +0.1 | – |
| Rafael Flores | C/1B | PIT | Trade | 2025 | 1 | +0.2 | +0.2 | – |
| Marco Gonzales | P | PIT | Trade | 2023 | 1 | +0.2 | +0.2 | 0.0 |
| Kyle Nicolas | P | PIT | Draft | 2023 | 2 | +0.2 | +0.1 | – |
| Tommy Pham | OF | PIT | Free agency | 2025 | 1 | +0.2 | +0.2 | 0.1 |
| Zach Thompson | P | PIT | Trade | 2021 | 1 | +0.2 | +0.2 | 0.0 |
| Kevin Jarvis | P | BOS | Trade | 2006 | 1 | +0.2 | +0.2 | 0.1 |
| Jason Johnson | P | BOS | Trade | 2006 | 1 | +0.2 | +0.2 | 0.1 |
| Matt Thornton | P | BOS | Trade | 2013 | 1 | +0.2 | +0.2 | 0.8 |
| Nik Turley | P | PIT | Trade | 2020 | 1 | +0.2 | +0.2 | 0.1 |
| Manny Banuelos | P | PIT | Trade | 2022 | 1 | +0.2 | +0.2 | 0.0 |
| Anthony Alford | OF | PIT | Trade | 2021 | 1 | +0.2 | +0.2 | 0.0 |
| Miguel Andújar | 3B/OF | PIT | Trade | 2023 | 1 | +0.2 | +0.2 | 0.0 |
| Thomas Hatch | P | PIT | Trade | 2023 | 1 | +0.2 | +0.2 | 0.0 |
| Jake Woodford | P | PIT | Trade | 2024 | 1 | +0.2 | +0.2 | 0.0 |
| Tyler Callihan | OF | PIT | Trade | 2026 | 1 | +0.2 | +0.2 | 1.3 |
| Bryan Corey | P | BOS | Trade | 2006 | 2 | +0.1 | +0.1 | 0.1 |
| Devern Hansack | P | BOS | Trade | 2006 | 2 | +0.1 | +0.0 | – |
| Justin Masterson | P | BOS | Draft | 2006 | 2 | +0.1 | +0.1 | – |
| Carlos Peña | 1B | BOS | Free agency | 2006 | 1 | +0.1 | +0.1 | 0.0 |
| Michael Chavis | 1B/2B | BOS | Draft | 2014 | 1 | +0.1 | +0.1 | – |
| Sean O'Sullivan | P | BOS | Free agency | 2015 | 1 | +0.1 | +0.1 | 0.7 |
| Josh Rutledge | 2B/SS | BOS | Trade | 2015 | 2 | +0.1 | +0.0 | 0.3 |
| Anthony Varvaro | P | BOS | Free agency | 2015 | 1 | +0.1 | +0.1 | 0.2 |
| Austin Brice | P | PIT | Free agency | 2022 | 1 | +0.1 | +0.1 | 0.0 |
| Taylor Davis | C | PIT | Trade | 2021 | 1 | +0.1 | +0.1 | 0.0 |
| Wilmer Difo | 2B/SS | PIT | Free agency | 2021 | 1 | +0.1 | +0.1 | 0.0 |
| Wilber Dotel | P | PIT | Draft | 2026 | 1 | +0.1 | +0.1 | – |
| Liover Peguero | 2B/SS | PIT | Draft | 2022 | 3 | +0.1 | +0.0 | – |
| Brett Sullivan | C | PIT | Trade | 2025 | 1 | +0.1 | +0.1 | 0.0 |
| Rob Zastryzny | P | PIT | Free agency | 2023 | 1 | +0.1 | +0.1 | 0.0 |
| Mike Burns | P | BOS | Trade | 2006 | 1 | +0.1 | +0.1 | 0.1 |
| Nick Punto | 2B/3B/SS | BOS | Trade | 2012 | 1 | +0.1 | +0.1 | 0.1 |
| Justin Germano | P | BOS | Trade | 2012 | 1 | +0.1 | +0.1 | 0.1 |
| Pedro Beato | P | BOS | Trade | 2012 | 1 | +0.1 | +0.1 | 0.0 |
| Ben Gamel | OF | PIT | Trade | 2021 | 2 | +0.1 | +0.0 | 0.0 |
| Guillermo Heredia | OF | PIT | Trade | 2020 | 1 | +0.1 | +0.1 | 0.0 |
| Tim Mayza | P | PIT | Trade | 2025 | 1 | +0.1 | +0.1 | 0.0 |
| Connor Overton | P | PIT | Trade | 2021 | 1 | +0.1 | +0.1 | 0.0 |
| Tanner Rainey | P | PIT | Trade | 2025 | 1 | +0.1 | +0.1 | 0.0 |
| Enmanuel Valdez | 2B | PIT | Trade | 2025 | 1 | +0.1 | +0.1 | 0.0 |
| Aaron Bates | 1B | BOS | Draft | 2006 | – | -0.0 | – | – |
| George Kottaras | C | BOS | Trade | 2006 | – | -0.0 | – | – |
| Jeff Bianchi | 3B/SS | BOS | Free agency | 2015 | – | -0.0 | – | – |
| Corey Brown | OF | BOS | Free agency | 2014 | 1 | +0.0 | +0.0 | 0.0 |
| Edwin Escobar | P | BOS | Trade | 2014 | 1 | +0.0 | +0.0 | – |
| Darwinzon Hernández | P | BOS | Intl FA | 2013 | 2 | +0.0 | +0.0 | – |
| Mike Miller | 2B | BOS | Draft | 2012 | – | -0.0 | – | – |
| Cam Alldred | P | PIT | Draft | 2022 | 1 | +0.0 | +0.0 | – |
| Justin Bruihl | P | PIT | Free agency | 2024 | – | -0.0 | – | – |
| Vinny Capra | 3B | PIT | Trade | 2023 | – | -0.0 | – | – |
| Billy Cook | OF | PIT | Trade | 2024 | 1 | -0.0 | -0.0 | – |
| Chris Devenski | P | PIT | Free agency | 2026 | – | -0.0 | – | – |
| Josh Fleming | P | PIT | Free agency | 2024 | – | -0.0 | – | – |
| Drew Maggi | 3B/DH | PIT | Trade | 2022 | 1 | +0.0 | +0.0 | – |
| Ryder Ryan | P | PIT | Free agency | 2023 | – | -0.0 | – | – |
| Colin Selby | P | PIT | Draft | 2023 | – | -0.0 | – | – |
| Andrew Susac | C | PIT | Free agency | 2020 | – | -0.0 | – | – |
| José Urquidy | P | PIT | Free agency | 2026 | 1 | +0.0 | +0.0 | 0.3 |
| Cam Vieaux | P | PIT | Draft | 2022 | – | -0.0 | – | – |
| Chris Capuano | P | BOS | Trade | 2014 | 1 | +0.0 | +0.0 | 0.0 |
| Jonathan Herrera | 2B/SS | BOS | Trade | 2014 | 1 | +0.0 | +0.0 | 0.0 |
| Justin Thomas | P | BOS | Trade | 2012 | 1 | +0.0 | +0.0 | 0.0 |
| Robbie Erlin | P | PIT | Trade | 2020 | 1 | +0.0 | +0.0 | 0.0 |
| Robert Stephenson | P | PIT | Trade | 2022 | 1 | -0.0 | -0.0 | 0.0 |
| Anthony Banda | P | PIT | Trade | 2022 | 1 | +0.0 | +0.0 | 0.0 |
| Greg Allen | OF | PIT | Trade | 2022 | 1 | +0.0 | +0.0 | 0.0 |
| Austin Davis | P | PIT | Trade | 2020 | 1 | +0.0 | +0.0 | 0.0 |
| Enyel De Los Santos | P | PIT | Trade | 2021 | 1 | +0.0 | +0.0 | 0.0 |
| Alfonso Rivas | 1B | PIT | Trade | 2023 | 1 | +0.0 | +0.0 | 0.0 |
| Michael Darrell-Hicks | P | PIT | Trade | 2025 | 1 | +0.0 | +0.0 | 0.0 |
| Mike Holtz | P | BOS | Free agency | 2006 | – | -0.1 | – | – |
| Ken Huckaby | C | BOS | Free agency | 2006 | – | -0.1 | – | – |
| Corky Miller | C | BOS | Free agency | 2006 | – | -0.1 | – | – |
| Dustan Mohr | OF | BOS | Free agency | 2006 | – | -0.1 | – | – |
| José De La Torre | P | BOS | Trade | 2012 | – | -0.1 | – | – |
| Jonathan Diaz | SS | BOS | Trade | 2013 | – | -0.1 | – | – |
| Ryan LaMarre | OF | BOS | Free agency | 2015 | – | -0.1 | – | – |
| Kyle Martin | P | BOS | Draft | 2013 | – | -0.1 | – | – |
| Yoán Moncada | 3B | BOS | Intl FA | 2015 | – | -0.1 | – | – |
| Jason Repko | OF | BOS | Free agency | 2012 | – | -0.1 | – | – |
| Ben Taylor | P | BOS | Draft | 2015 | – | -0.1 | – | – |
| Tsung-Che Cheng | SS | PIT | Draft | 2025 | – | -0.1 | – | – |
| Brady Feigl | P | PIT | Draft | 2024 | – | -0.1 | – | – |
| Ben Heller | P | PIT | Free agency | 2023 | – | -0.1 | – | – |
| Jose Hernandez | P | PIT | Draft | 2023 | 1 | -0.1 | -0.1 | – |
| Grant Koch | C | PIT | Draft | 2024 | – | -0.1 | – | – |
| J. R. Murphy | C | PIT | Free agency | 2020 | – | -0.1 | – | – |
| Chasen Shreve | P | PIT | Free agency | 2021 | – | -0.1 | – | – |
| Shea Spitzbarth | P | PIT | Rule 5 | 2020 | – | -0.1 | – | – |
| Troy Stokes | OF | PIT | Trade | 2021 | – | -0.1 | – | – |
| Davis Wendzel | 3B | PIT | Free agency | 2025 | – | -0.1 | – | – |
| Rudy Seánez | P | BOS | Trade | 2006 | 1 | -0.1 | -0.1 | 0.0 |
| Yacksel Ríos | P | PIT | Trade | 2020 | 1 | -0.1 | -0.1 | 0.0 |
| Eduard Bazardo | P | BOS | Intl FA | 2014 | 1 | -0.2 | -0.2 | – |
| Roenis Elías | P | BOS | Trade | 2015 | – | -0.2 | – | – |
| Mauro Gómez | 1B/3B | BOS | Trade | 2012 | – | -0.2 | – | – |
| Trevor Kelley | P | BOS | Draft | 2015 | – | -0.2 | – | – |
| Ryan Roberts | 2B/3B | BOS | Free agency | 2014 | – | -0.2 | – | – |
| Brandon Snyder | 1B/3B | BOS | Free agency | 2013 | – | -0.2 | – | – |
| Cody Bolton | P | PIT | Draft | 2023 | – | -0.2 | – | – |
| Jerad Eickhoff | P | PIT | Free agency | 2021 | – | -0.2 | – | – |
| Domingo Germán | P | PIT | Free agency | 2024 | – | -0.2 | – | – |
| Cam Sanders | P | PIT | Draft | 2025 | – | -0.2 | – | – |
| Travis Swaggerty | OF | PIT | Draft | 2022 | – | -0.2 | – | – |
| Bryse Wilson | P | PIT | Trade | 2021 | – | -0.2 | – | – |
| Lars Anderson | 1B | BOS | Draft | 2006 | – | -0.3 | – | – |
| Dustin Richardson | P | BOS | Draft | 2006 | 1 | -0.3 | -0.3 | – |
| J. T. Snow | 1B | BOS | Free agency | 2006 | – | -0.3 | – | – |
| Chris Carpenter | P | BOS | Trade | 2012 | – | -0.3 | – | – |
| Ryan Hanigan | C | BOS | Trade | 2014 | 1 | -0.3 | -0.3 | 1.3 |
| Allen Webster | P | BOS | Trade | 2012 | 1 | -0.3 | -0.3 | – |
| Hunter Barco | P | PIT | Draft | 2025 | 1 | -0.3 | -0.3 | – |
| Diego Castillo | 2B/SS | PIT | Draft | 2022 | – | -0.3 | – | – |
| Matt Gorski | 1B/OF | PIT | Draft | 2025 | – | -0.3 | – | – |
| Tom Harrington | P | PIT | Draft | 2025 | – | -0.3 | – | – |
| Derek Holland | P | PIT | Free agency | 2020 | – | -0.3 | – | – |
| Luis Oviedo | P | PIT | Trade | 2020 | – | -0.3 | – | – |
| Chris Owings | 2B/SS | PIT | Free agency | 2023 | – | -0.3 | – | – |
| Nick Yorke | 2B/3B | PIT | Trade | 2024 | – | -0.3 | – | – |
| Kyle Snyder | P | BOS | Trade | 2006 | 1 | -0.3 | -0.3 | 0.2 |
| Phillip Evans | 3B/OF | PIT | Trade | 2020 | 1 | -0.3 | -0.3 | 0.1 |
| Sam Howard | P | PIT | Trade | 2020 | 1 | -0.3 | -0.3 | 0.0 |
| Aaron Cook | P | BOS | Free agency | 2012 | – | -0.4 | – | – |
| Cam Devanney | 3B | PIT | Trade | 2025 | – | -0.4 | – | – |
| Todd Frazier | 3B | PIT | Free agency | 2021 | – | -0.4 | – | – |
| Nick Solak | 2B | PIT | Free agency | 2024 | – | -0.4 | – | – |
| Clayton Mortensen | P | BOS | Trade | 2012 | – | -0.5 | – | – |
| Tucupita Marcano | 2B/SS/OF | PIT | Trade | 2021 | – | -0.5 | – | – |
| Hoy Park | 2B | PIT | Trade | 2021 | 1 | -0.5 | -0.5 | – |
| Canaan Smith-Njigba | OF | PIT | Draft | 2022 | – | -0.5 | – | – |
| Rowdy Tellez | 1B | PIT | Free agency | 2023 | – | -0.5 | – | – |
| Willie Harris | 2B/OF | BOS | Free agency | 2006 | – | -0.6 | – | – |
| Ryan Kalish | OF | BOS | Draft | 2006 | 1 | -0.6 | -0.6 | – |
| Tzu-Wei Lin | 2B/SS | BOS | Intl FA | 2012 | 2 | -0.6 | -0.3 | – |
| Bligh Madris | 1B/OF | PIT | Draft | 2022 | – | -0.6 | – | – |
| Quinn Priester | P | PIT | Draft | 2023 | 1 | -0.6 | -0.6 | – |
| Erik González | 3B/SS | PIT | Trade | 2020 | 1 | -0.6 | -0.6 | 0.1 |
| Joel Hanrahan | P | BOS | Trade | 2012 | – | -0.7 | – | – |
| Ji Hwan Bae | 2B/OF | PIT | Draft | 2022 | 1 | -0.7 | -0.7 | – |
| Michael Chavis | 1B/2B | PIT | Trade | 2021 | 1 | -0.7 | -0.7 | 0.0 |
| Wil Crowe | P | PIT | Trade | 2020 | – | -0.7 | – | – |
| Cal Mitchell | OF | PIT | Draft | 2022 | – | -0.7 | – | – |
| Alika Williams | SS | PIT | Trade | 2023 | – | -0.7 | – | – |
| Marco Hernández | 2B | BOS | Trade | 2014 | – | -0.8 | – | – |
| Alexi Ogando | P | BOS | Free agency | 2015 | – | -0.8 | – | – |
| Sam Travis | 1B/OF | BOS | Draft | 2014 | – | -0.8 | – | – |
| Marcell Ozuna | DH/OF | PIT | Free agency | 2026 | – | -0.8 | – | – |
| Josh VanMeter | 2B | PIT | Trade | 2022 | – | -0.8 | – | – |
| Allen Craig | 1B/OF | BOS | Trade | 2014 | – | -0.9 | – | – |
| Deven Marrero | 3B | BOS | Draft | 2012 | – | -0.9 | – | – |
| Edward Olivares | OF | PIT | Trade | 2023 | – | -0.9 | – | – |
| JT Riddle | SS | PIT | Free agency | 2020 | – | -0.9 | – | – |
| Craig Breslow | P | BOS | Trade | 2012 | 3 | -1.0 | -0.3 | 0.1 |
| Chase De Jong | P | PIT | Free agency | 2021 | – | -1.1 | – | – |
| Yoshi Tsutsugo | 1B/DH/OF | PIT | Free agency | 2021 | 1 | -1.3 | -1.3 | 0.0 |
| Pablo Sandoval | 3B | BOS | Free agency | 2014 | – | -1.4 | – | – |
| Henry Davis | C | PIT | Draft | 2023 | 1 | -1.4 | -1.4 | – |
WAB = wins above what the team's payroll predicted (resource-controlled). WAR surplus = era-neutral value (WAR minus payroll in win-equivalents). Roster surplus $M = dollar value of WAR over cost. Build channels (realized fWAR): HG = home-grown via amateur draft / international signing; Trade = acquired minus surrendered (incl. purchases/waivers); FA = signed minus walked; R5 = Rule-5 / minor-league-draft pickups. Credit follows the acquisition year — home-grown to the regime at the player's draft/signing (not whoever was in the chair when he peaked), trade/FA/R5 to the GM who made the move. Players acquired as prospects before debuting (e.g. Smoltz, Bagwell; Rule-5 picks like Uggla) are counted as trade/R5, not home-grown. All are franchise-level outcomes during the stint, not solely attributable to one executive.