Born Dec 29, 1973 · New York City, NY · age 52
Ended two of the sport's most famous championship droughts — building the Red Sox club that won in 2004 (their first since 1918) and the Cubs team that won in 2016 (their first since 1908). One of the defining executives of the analytics era.
17 seasons with salary-era data across 3 stints. All figures are franchise-level outcomes during the tenure, not solely attributable to one executive.
Share of gross-positive acquired fWAR by channel (vs. league average).
Acquired minus surrendered / signed minus walked.
| Team | Role | Years | Szns | WAB | WAB/yr | TAB | WAR surp | HG | Trade | FA | R5 | AcqLev | W-L% | PO | Pen | WS | Surp $M |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| ▸ Cubs | POBO | 2012–2020 | 8 | +7.1 | +0.89 | +22.1 | -59.7 | +100.3 | +45.0 | -6.5 | +0.6 | 1.38 | 0.520 | 5 | 1 | 1 | -230 |
| ▸ Red Sox | GM | 2007–2011 | 5 | +25.1 | +5.02 | +33.1 | -79.8 | +126.7 | -4.4 | -48.7 | +0.0 | 2.72 | 0.574 | 3 | 1 | 1 | -184 |
| ▸ Red Sox | GM | 2003–2005 | 3 | +21.1 | +7.05 | +18.3 | -60.0 | +100.5 | -39.9 | -27.2 | -0.2 | 1.66 | 0.593 | 3 | 1 | 1 | -107 |
| Career total (1985+ data) | 17 | +53.4 | +73.6 | -199.5 | +327.5 | +0.8 | -82.5 | +0.3 | 1.78 | 0.550 | 11 | 3 | 3 | -520 | |||
| Player | Pos | Team | How | Year | fWAR |
|---|---|---|---|---|---|
| David Ortiz | DH | BOS | Free agency | 2003 | +48.8 |
| Dustin Pedroia | 2B | BOS | Draft | 2004 | +44.8 |
| Mookie Betts | OF | BOS | Draft | 2011 | +34.6 |
| Xander Bogaerts | SS | BOS | Intl FA | 2009 | +34.1 |
| Anthony Rizzo | 1B | CHC | Trade | 2012 | +31.1 |
| Kris Bryant | 3B/OF | CHC | Draft | 2013 | +27.9 |
| Kyle Hendricks | P | CHC | Trade | 2012 | +24.4 |
| Ian Happ | OF | CHC | Draft | 2015 | +22.4 |
| Jacoby Ellsbury | OF | BOS | Draft | 2005 | +22.2 |
| Nico Hoerner | 2B/SS | CHC | Draft | 2018 | +21.3 |
| Josh Beckett | P | BOS | Trade | 2005 | +20.1 |
| Jake Arrieta | P | CHC | Trade | 2013 | +19.6 |
| Jon Lester | P | CHC | Free agency | 2014 | +17.0 |
| Jackie Bradley | OF | BOS | Draft | 2011 | +16.3 |
| Clay Buchholz | P | BOS | Draft | 2005 | +14.2 |
| Jonathan Papelbon | P | BOS | Draft | 2003 | +14.1 |
| J. D. Drew | OF | BOS | Free agency | 2007 | +12.9 |
| Curt Schilling | P | BOS | Trade | 2003 | +12.8 |
| Christian Vázquez | C | BOS | Draft | 2008 | +11.8 |
| Addison Russell | SS | CHC | Trade | 2014 | +11.7 |
| Justin Steele | P | CHC | Draft | 2014 | +10.2 |
| Bill Mueller | 3B | BOS | Free agency | 2003 | +9.3 |
| Jarrod Saltalamacchia | C | BOS | Trade | 2010 | +8.8 |
| Daisuke Matsuzaka | P | BOS | Draft | 2007 | +7.8 |
| Kyle Schwarber | DH/OF | CHC | Draft | 2014 | +7.7 |
| Jason Heyward | OF | CHC | Free agency | 2015 | +7.2 |
| John Lackey | P | BOS | Free agency | 2009 | +6.8 |
| Ben Zobrist | 2B/OF | CHC | Free agency | 2015 | +6.6 |
| Adrian Beltré | 3B | BOS | Free agency | 2010 | +6.4 |
| Mike Lowell | 3B | BOS | Free agency | 2007 | +6.2 |
| Daniel Nava | OF | BOS | Draft | 2010 | +6.0 |
| Chris Coghlan | OF | CHC | Free agency | 2014 | +5.5 |
| Yu Darvish | P | CHC | Free agency | 2018 | +5.4 |
| Matt Barnes | P | BOS | Draft | 2011 | +4.9 |
| Marco Scutaro | 2B/SS | BOS | Free agency | 2009 | +4.7 |
| Pedro Strop | P | CHC | Trade | 2013 | +4.7 |
| Jose Quintana | P | CHC | Trade | 2017 | +4.6 |
| Miguel Montero | C | CHC | Trade | 2014 | +4.5 |
| Dexter Fowler | OF | CHC | Free agency | 2016 | +4.3 |
| Jason Hammel | P | CHC | Free agency | 2014 | +4.1 |
| Junichi Tazawa | P | BOS | Draft | 2009 | +4.0 |
| Héctor Rondón | P | CHC | Rule 5 | 2012 | +4.0 |
| Patrick Wisdom | 3B | CHC | Free agency | 2020 | +3.9 |
| Víctor Martínez | C/DH | BOS | Trade | 2009 | +3.7 |
| Félix Doubront | P | BOS | Intl FA | 2005 | +3.5 |
| Jed Lowrie | 2B/SS | BOS | Draft | 2005 | +3.5 |
| Rich Hill | P | BOS | Free agency | 2010 | +3.5 |
| Mike Timlin | P | BOS | Free agency | 2003 | +3.3 |
| John Lackey | P | CHC | Free agency | 2015 | +3.2 |
| David Bote | 2B/3B | CHC | Draft | 2012 | +3.1 |
| David Wells | P | BOS | Free agency | 2004 | +3.0 |
| Albert Almora | OF | CHC | Draft | 2012 | +3.0 |
| Dexter Fowler | OF | CHC | Trade | 2015 | +3.0 |
| Matt Clement | P | BOS | Free agency | 2004 | +2.9 |
| Edwin Jackson | P | CHC | Free agency | 2013 | +2.9 |
| Hideki Okajima | P | BOS | Draft | 2007 | +2.8 |
| Brandon Workman | P | BOS | Draft | 2010 | +2.8 |
| Mike Montgomery | P | CHC | Trade | 2016 | +2.8 |
| Carl Edwards | P | CHC | Trade | 2013 | +2.7 |
| David Ross | C | BOS | Free agency | 2008 | +2.5 |
| Cole Hamels | P | CHC | Trade | 2018 | +2.5 |
| Chris Martin | P | BOS | Free agency | 2011 | +2.4 |
| Curt Schilling | P | BOS | Free agency | 2007 | +2.3 |
| Rafael Ortega | OF | CHC | Free agency | 2020 | +2.3 |
| Carlos Villanueva | P | CHC | Free agency | 2013 | +2.3 |
| Adbert Alzolay | P | CHC | Intl FA | 2012 | +2.2 |
| Dioner Navarro | C | CHC | Free agency | 2012 | +2.2 |
| Colin Rea | P | CHC | Free agency | 2019 | +2.2 |
| Drew Smyly | P | CHC | Free agency | 2017 | +1.9 |
| Édgar Rentería | SS | BOS | Free agency | 2004 | +1.8 |
| David Ross | C | CHC | Free agency | 2014 | +1.7 |
| Will Middlebrooks | 3B | BOS | Draft | 2007 | +1.6 |
| Tommy La Stella | 2B/3B | CHC | Trade | 2014 | +1.6 |
| Mike Aviles | SS | BOS | Trade | 2011 | +1.5 |
| Nate Schierholtz | OF | CHC | Free agency | 2012 | +1.5 |
| Jorge Soler | DH/OF | CHC | Intl FA | 2012 | +1.4 |
| Keith Foulke | P | BOS | Free agency | 2004 | +1.3 |
| Travis Shaw | 3B | BOS | Draft | 2011 | +1.3 |
| Justin Grimm | P | CHC | Trade | 2013 | +1.3 |
| Ryan Sweeney | OF | CHC | Free agency | 2013 | +1.3 |
| Doug Mirabelli | C | BOS | Free agency | 2004 | +1.2 |
| Blake Swihart | C/OF | BOS | Draft | 2011 | +1.2 |
| Víctor Caratini | C | CHC | Trade | 2014 | +1.2 |
| Matt Duffy | 3B | CHC | Free agency | 2020 | +1.2 |
| Jon Jay | OF | CHC | Free agency | 2016 | +1.2 |
| Wade Miller | P | BOS | Free agency | 2004 | +1.1 |
| Donnie Murphy | 2B/3B/SS | CHC | Free agency | 2013 | +1.1 |
| Steve Cishek | P | CHC | Free agency | 2017 | +1.0 |
| Neil Ramírez | P | CHC | Trade | 2013 | +1.0 |
| Tsuyoshi Wada | P | CHC | Draft | 2014 | +1.0 |
| Scott Atchison | P | BOS | Free agency | 2007 | +0.9 |
| Brian Bogusevic | OF | CHC | Free agency | 2012 | +0.9 |
| Brandon Kintzler | P | CHC | Trade | 2018 | +0.9 |
| Tyler Chatwood | P | CHC | Free agency | 2017 | +0.8 |
| Andrew Miller | P | BOS | Free agency | 2010 | +0.7 |
| Ryan Sweeney | OF | BOS | Trade | 2011 | +0.7 |
| Keegan Thompson | P | CHC | Draft | 2017 | +0.7 |
| Gabe Kapler | OF | BOS | Free agency | 2003 | +0.6 |
| Darnell McDonald | OF | BOS | Free agency | 2009 | +0.6 |
| Brandon Morrow | P | CHC | Free agency | 2017 | +0.6 |
| Koji Uehara | P | CHC | Free agency | 2016 | +0.6 |
| Rocco Baldelli | OF | BOS | Free agency | 2009 | +0.5 |
| Bartolo Colón | P | BOS | Free agency | 2008 | +0.5 |
| John Olerud | 1B | BOS | Free agency | 2005 | +0.4 |
| Jeff Bailey | 1B | BOS | Trade | 2007 | +0.4 |
| Drake Britton | P | BOS | Draft | 2007 | +0.4 |
| Henry Owens | P | BOS | Draft | 2011 | +0.4 |
| Drew Sutton | 2B/OF | BOS | Free agency | 2010 | +0.4 |
| Chris Denorfia | OF | CHC | Free agency | 2015 | +0.4 |
| Jason Kipnis | 2B | CHC | Free agency | 2020 | +0.4 |
| Jason Motte | P | CHC | Free agency | 2014 | +0.4 |
| Clayton Richard | P | CHC | Free agency | 2015 | +0.4 |
| Rob Zastryzny | P | CHC | Draft | 2013 | +0.4 |
| Chad Bradford | P | BOS | Trade | 2005 | +0.3 |
| Carl Crawford | OF | BOS | Free agency | 2010 | +0.3 |
| Ramón Ramírez | P | BOS | Trade | 2008 | +0.3 |
| Takashi Saito | P | BOS | Free agency | 2009 | +0.3 |
| Dan Wheeler | P | BOS | Free agency | 2010 | +0.3 |
| Munenori Kawasaki | 2B/SS | CHC | Free agency | 2016 | +0.3 |
| Ryan Tepera | P | CHC | Free agency | 2019 | +0.3 |
| Wesley Wright | P | CHC | Free agency | 2013 | +0.3 |
| Michael Bowden | P | BOS | Draft | 2005 | +0.2 |
| Geremi González | P | BOS | Free agency | 2005 | +0.2 |
| David Pauley | P | BOS | Trade | 2004 | +0.2 |
| Pokey Reese | 2B/SS | BOS | Free agency | 2003 | +0.2 |
| Paul Byrd | P | BOS | Free agency | 2009 | +0.2 |
| Garin Cecchini | 3B | BOS | Draft | 2010 | +0.2 |
| Alex Wilson | P | BOS | Draft | 2009 | +0.2 |
| Jason Adam | P | CHC | Free agency | 2020 | +0.2 |
| Anthony Bass | P | CHC | Free agency | 2017 | +0.2 |
| Scott Effross | P | CHC | Draft | 2015 | +0.2 |
| Kyuji Fujikawa | P | CHC | Draft | 2013 | +0.2 |
| Jeremy Jeffress | P | CHC | Free agency | 2020 | +0.2 |
| Lenny DiNardo | P | BOS | Rule 5 | 2003 | +0.1 |
| Byung-Hyun Kim | P | BOS | Trade | 2003 | +0.1 |
| Alejandro Machado | 2B/OF | BOS | Trade | 2005 | +0.1 |
| Dave McCarty | 1B/OF | BOS | Free agency | 2003 | +0.1 |
| Robert Person | P | BOS | Free agency | 2003 | +0.1 |
| Alfredo Aceves | P | BOS | Free agency | 2011 | +0.1 |
| Matt Albers | P | BOS | Free agency | 2010 | +0.1 |
| Kevin Cash | C | BOS | Free agency | 2007 | +0.1 |
| Robert Coello | P | BOS | Trade | 2010 | +0.1 |
| Jake Buchanan | P | CHC | Free agency | 2016 | +0.1 |
| Jaye Chapman | P | CHC | Trade | 2012 | +0.1 |
| Gerardo Concepción | P | CHC | Intl FA | 2012 | +0.1 |
| Robel García | 2B | CHC | Trade | 2019 | +0.1 |
| P. J. Higgins | C/1B | CHC | Draft | 2015 | +0.1 |
| Danny Hultzen | P | CHC | Trade | 2019 | +0.1 |
| Darnell McDonald | OF | CHC | Free agency | 2013 | +0.1 |
| James Norwood | P | CHC | Draft | 2014 | +0.1 |
| Alfonso Rivas | 1B | CHC | Trade | 2020 | +0.1 |
| Jamie Brown | P | BOS | Trade | 2003 | +0.0 |
| Lou Collier | SS | BOS | Free agency | 2003 | -0.0 |
| Tommy Hottovy | P | BOS | Draft | 2004 | -0.0 |
| Roberto Petagine | 1B | BOS | Free agency | 2005 | +0.0 |
| Shawn Wooten | 1B/DH | BOS | Free agency | 2005 | -0.0 |
| Joey Gathright | OF | BOS | Free agency | 2011 | +0.0 |
| Nick Green | 2B/SS | BOS | Free agency | 2009 | -0.0 |
| Bobby Jenks | P | BOS | Free agency | 2010 | +0.0 |
| Jonathan Van Every | OF | BOS | Trade | 2010 | +0.0 |
| Randy Williams | P | BOS | Free agency | 2010 | +0.0 |
| Quintin Berry | OF | CHC | Free agency | 2015 | +0.0 |
| Joe Biagini | P | CHC | Free agency | 2020 | +0.0 |
| J. C. Boscán | C | CHC | Free agency | 2012 | +0.0 |
| Xavier Cedeño | P | CHC | Free agency | 2019 | -0.0 |
| Tim Collins | P | CHC | Free agency | 2019 | -0.0 |
| Matt Dermody | P | CHC | Free agency | 2020 | +0.0 |
| Mike Freeman | 2B | CHC | Free agency | 2017 | -0.0 |
| Kevin Gregg | P | CHC | Free agency | 2013 | +0.0 |
| Pierce Johnson | P | CHC | Draft | 2012 | +0.0 |
| Rodrigo López | P | CHC | Free agency | 2012 | -0.0 |
| Brailyn Márquez | P | CHC | Intl FA | 2015 | -0.0 |
| Ian Miller | OF | CHC | Free agency | 2019 | +0.0 |
| Tyler Payne | C | CHC | Draft | 2015 | -0.0 |
| Hernán Pérez | 2B/3B/OF | CHC | Free agency | 2019 | -0.0 |
| Zach Putnam | P | CHC | Free agency | 2012 | -0.0 |
| Kyle Ryan | P | CHC | Free agency | 2018 | +0.0 |
| Pedro Strop | P | CHC | Free agency | 2020 | +0.0 |
| Arodys Vizcaíno | P | CHC | Trade | 2012 | -0.0 |
| Pedro Astacio | P | BOS | Free agency | 2004 | -0.1 |
| Adrian Brown | OF | BOS | Free agency | 2003 | -0.1 |
| Craig Hansen | P | BOS | Draft | 2005 | -0.1 |
| Rudy Seánez | P | BOS | Free agency | 2003 | -0.1 |
| Phil Seibel | P | BOS | Trade | 2003 | -0.1 |
| David Aardsma | P | BOS | Trade | 2008 | -0.1 |
| Jonathan Aro | P | BOS | Intl FA | 2011 | -0.1 |
| Bryce Brentz | OF | BOS | Draft | 2010 | -0.1 |
| Sean Casey | 1B | BOS | Free agency | 2008 | -0.1 |
| Enrique González | P | BOS | Free agency | 2008 | -0.1 |
| Alex Hassan | OF | BOS | Draft | 2009 | -0.1 |
| Che-Hsuan Lin | OF | BOS | Intl FA | 2007 | -0.1 |
| Dennys Reyes | P | BOS | Free agency | 2011 | -0.1 |
| Scott Schoeneweis | P | BOS | Free agency | 2010 | -0.1 |
| Joe Thurston | 2B/3B | BOS | Free agency | 2007 | -0.1 |
| Jim Adduci | 1B/OF | CHC | Free agency | 2018 | -0.1 |
| Tony Barnette | P | CHC | Free agency | 2019 | -0.1 |
| Mike Baxter | OF | CHC | Free agency | 2015 | -0.1 |
| Trevor Cahill | P | CHC | Free agency | 2015 | -0.1 |
| Brian Duensing | P | CHC | Free agency | 2016 | -0.1 |
| Seth Frankoff | P | CHC | Trade | 2017 | -0.1 |
| Justin Hancock | P | CHC | Trade | 2017 | -0.1 |
| Michael Hermosillo | OF | CHC | Free agency | 2020 | -0.1 |
| Chang-Yong Lim | P | CHC | Draft | 2013 | -0.1 |
| Tyson Miller | P | CHC | Draft | 2016 | -0.1 |
| Efren Navarro | 1B/OF | CHC | Free agency | 2018 | -0.1 |
| Steven Souza | OF | CHC | Free agency | 2020 | -0.1 |
| Hisanori Takahashi | P | CHC | Free agency | 2012 | -0.1 |
| Taylor Teagarden | C | CHC | Free agency | 2014 | -0.1 |
| Jen-Ho Tseng | P | CHC | Intl FA | 2013 | -0.1 |
| Duane Underwood | P | CHC | Draft | 2012 | -0.1 |
| Chris Valaika | 2B | CHC | Free agency | 2013 | -0.1 |
| Mark Zagunis | OF | CHC | Draft | 2014 | -0.1 |
| Andy Dominique | C/1B | BOS | Trade | 2004 | -0.2 |
| Hunter Jones | P | BOS | Intl FA | 2005 | -0.2 |
| Matt Mantei | P | BOS | Free agency | 2004 | -0.2 |
| Cla Meredith | P | BOS | Draft | 2004 | -0.2 |
| David Murphy | OF | BOS | Draft | 2003 | -0.2 |
| Dan Butler | C | BOS | Intl FA | 2009 | -0.2 |
| Mike Cameron | OF | BOS | Free agency | 2009 | -0.2 |
| Chris Carter | OF | BOS | Trade | 2007 | -0.2 |
| William Cuevas | P | BOS | Intl FA | 2008 | -0.2 |
| Jose Iglesias | SS | BOS | Intl FA | 2009 | -0.2 |
| Gustavo Molina | C | BOS | Free agency | 2010 | -0.2 |
| Ryan Shealy | 1B | BOS | Free agency | 2010 | -0.2 |
| Nate Spears | 2B/OF | BOS | Trade | 2011 | -0.2 |
| Billy Traber | P | BOS | Free agency | 2008 | -0.2 |
| Gil Velazquez | 3B | BOS | Trade | 2008 | -0.2 |
| Scott Baker | P | CHC | Free agency | 2012 | -0.2 |
| Tim Federowicz | C | CHC | Free agency | 2016 | -0.2 |
| Trent Giambrone | 2B | CHC | Draft | 2016 | -0.2 |
| Jonathan Herrera | 2B/SS | CHC | Free agency | 2014 | -0.2 |
| Tommy Nance | P | CHC | Intl FA | 2016 | -0.2 |
| Spencer Patton | P | CHC | Trade | 2015 | -0.2 |
| Josh Phegley | C | CHC | Free agency | 2020 | -0.2 |
| Michael Rucker | P | CHC | Draft | 2016 | -0.2 |
| Rafael Soriano | P | CHC | Free agency | 2015 | -0.2 |
| Ian Stewart | 3B | CHC | Free agency | 2012 | -0.2 |
| Allen Webster | P | CHC | Free agency | 2018 | -0.2 |
| Andy Abad | 1B | BOS | Free agency | 2003 | -0.3 |
| Jason Shiell | P | BOS | Free agency | 2003 | -0.3 |
| Adam Stern | OF | BOS | Rule 5 | 2004 | -0.3 |
| Fernando Cabrera | P | BOS | Free agency | 2009 | -0.3 |
| Adrian Cardenas | 2B | CHC | Trade | 2012 | -0.3 |
| José Lobatón | C | CHC | Free agency | 2020 | -0.3 |
| Bobby Jones | P | BOS | Free agency | 2003 | -0.4 |
| Kyle Weiland | P | BOS | Draft | 2008 | -0.4 |
| Rex Brothers | P | CHC | Free agency | 2019 | -0.4 |
| Shawn Camp | P | CHC | Free agency | 2012 | -0.4 |
| Jake Jewell | P | CHC | Free agency | 2020 | -0.4 |
| Ryan Kalish | OF | CHC | Free agency | 2013 | -0.4 |
| Abe Alvarez | P | BOS | Draft | 2003 | -0.5 |
| Cory Abbott | P | CHC | Draft | 2017 | -0.5 |
| Eli Whiteside | C | CHC | Free agency | 2013 | -0.5 |
| Noé Ramirez | P | BOS | Draft | 2011 | -0.6 |
| Dan Winkler | P | CHC | Free agency | 2019 | -0.6 |
| Yamaico Navarro | 3B/SS | BOS | Intl FA | 2005 | -0.8 |
| Anthony Ranaudo | P | BOS | Draft | 2010 | -0.8 |
| Craig Kimbrel | P | CHC | Free agency | 2019 | -1.0 |
| Ryan Lavarnway | C | BOS | Draft | 2008 | -1.2 |
| John Baker | C | CHC | Free agency | 2013 | -1.2 |
| Joe Mather | OF | CHC | Free agency | 2012 | -1.2 |
| Daniel Descalso | 2B/3B | CHC | Free agency | 2018 | -1.3 |
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.