Chicago Bears–Las Vegas Raiders Trade History

Chicago received an undisclosed draft choice for quarterback Bob Cutburth on July 27, 1971. Cutburth had been a 1970 sixth-round Bears pick and had not appeared in an NFL regular-season game for Chicago; contemporary reporting confirms Oakland acquired him for an undisclosed choice. The Raiders did not receive demonstrated regular-season production from Cutburth, so the unidentified pick should not be treated as a known downstream player.

Oakland sent veteran defensive back Nemiah Wilson to Chicago for two future selections. The first became Jerome Dove, but the defining asset was the 1977 fifth-rounder used on Lester Hayes. Hayes developed into a five-time Pro Bowler, the 1980 AP Defensive Player of the Year and a cornerstone of two Raiders Super Bowl champions. Chicago received only a brief return from Wilson.

Chicago traded veteran deep threat Willie Gault to the Raiders for a 1989 first-round pick and 1990 third-rounder. The first became cornerback Donnell Woolford, who started 111 games for the Bears, intercepted 32 passes for Chicago, and earned a Pro Bowl selection. The Bears converted an established receiver into a younger long-term defensive starter and additional draft capital.

Chicago sent picks No. 110 and No. 165 to the Raiders in the 1989 draft and received pick No. 95, which the Bears used on Markus Paul. Paul became a multi-season Chicago defensive back and played 71 NFL games. Raiders selections Erik Affholter and Eric Mitchell produced little comparable value for the club, giving Chicago the stronger realized return.

The Raiders acquired Chicago's 1990 seventh-round choice at No. 173 and used it on Garry Lewis. The Bears moved three spots down to No. 176, Bill Anderson, and also received No. 298, Roman Matusz. It was a small late-round maneuver with little lasting separation. Oakland secured its preferred player, while Chicago added an extra selection, leaving the exchange appropriately even.

Chicago moved down from No. 40 to No. 48 in the 1999 second round and received Oakland's third-rounder while swapping fourth-round positions. The Bears used the package on Russell Davis, Marty Booker and Rosevelt Colvin. Booker became a Pro Bowl receiver and Colvin developed into a double-digit-sack edge defender. Oakland received Tony Bryant and Dameane Douglas, making Chicago's added depth and top-end production decisively better.

Chicago Bears received Shurron Pierson, while Las Vegas/Oakland Raiders received undisclosed draft choice. Chicago acquired Shurron Pierson, who appeared in six games for the Bears in 2004. Oakland received an undisclosed draft choice, but contemporary reporting does not reliably establish a draft year, round, slot, or downstream player, so the compensation should remain generic rather than be assigned to the already-completed 2004 draft. That outcome supports a C+ grade for Chicago Bears, a C for Las Vegas/Oakland Raiders, and a Chicago Bears Win verdict.

Chicago's trade for Khalil Mack gave the Bears an instant superstar and briefly turned their defense into one of the league's defining units. The Raiders received a major draft package, but the return never matched the value of an elite pass rusher in his prime. Chicago paid heavily, yet still acquired the best player. The deal remains a strong Bears win because Mack delivered superstar impact immediately, even if Chicago did not turn the window into a championship.

Chicago Bears received Eddy Pineiro in the 2019-05-06 exchange involving Las Vegas/Oakland Raiders. Pineiro handled Chicago's kicking job throughout 2019, making 23 of 28 field goals and 27 of 29 extra points and giving the Bears a usable starter for the season. That realized return supports a C+ grade for Chicago Bears. The overall verdict is Chicago Bears Win, with the grade based on direct value created from this transaction.