We can award it retroactively to 2000 when he first became a front office executive
2000: Chiefs lose Joe Horn to the Saints
2001: Steelers lose Mike Vrabel to the Patriots
2002: Buccaneers lose Warrick Dunn to the Falcons
2003: tough call here but I’m going Jake Plummer leaving the Cardinals for the Broncos because of who they drafted the very next season
2004: Titans lose Jevon Kearse to the Eagles
2005: Steelers lose Plaxico Burress to the Giants
2006: Chargers lose Drew Brees to the Saints
2007: Colts lose Jason Dav… lol jk. Bills lose Nate Clements to the 49ers
2008: Steelers lose Alan Faneca to the Jets
2009: Vikings lose some free safety to the Saints, allegedly
2010: Panthers lose Julius Peppers to the Bears
2011: Bengals lose Jonathan Joseph to the Texans
2012: Colts lose Peyton Manning to the Broncos
2013: Steelers lose Mike Wallace to the Dolphins
2014: Panthers lose Steve Smith to the Ravens
2015: Patriots lose Darrelle Revis to the Jets
2016: Packers lose Casey Hayward to the Chargers (Kelechi Osemele deserves a mention here after the Ravens lost him to the Raiders)
2017: Packers lose Tays… Cardinals lose Calais Campbell to the Jaguars
2018: Colts lose Vontae Davis to the Bills, who subsequently lost him to a halftime show. This is also the year the Saints signed Demario Davis from the Browns
2019: Giants lose Landon Collins to the Football Team
2020: Cowboys lose Byron Jones to the Dolphins
2021: Saints lose Trey Hendrickson to the Bengals
2022: Bears lose Khalil Mack to the Chargers
2023: Bengals lose Jessie Bates to the Falcons
2024: Giants lose Saquon Barkley to the Eagles