Chicago Bears–Dallas Cowboys Trade History

Chicago transferred quarterback Don Meredith to the expansion Cowboys on July 14, 1960 in exchange for Dallas's 1962 third-round choice, later No. 32 Jim Bates. The arrangement helped give the new franchise a recognizable Texas quarterback. Dallas earns an A+ because a third-round choice became a franchise quarterback and Ring of Honor figure. Chicago's return was real but ordinary. The gap between Bates's draft value and Meredith's nine-year Cowboys impact makes this a decisive Dallas win.

Dallas acquired Chuck Howley’s rights from Chicago on June 14, 1961, for second- and ninth-round picks in the 1963 draft. Howley became one of the defining linebackers in Cowboys history: 13 seasons with Dallas, six Pro Bowls, five first-team All-NFL selections, a Super Bowl VI championship, and Super Bowl V MVP honors. Chicago received No. 20 Steve Barnett and No. 118 Monte Day. Dallas won overwhelmingly.

Dallas purchased rookie tackle Clyde Brock from the Chicago Bears for $3,500 on July 1, 1962. Brock appeared in all 14 Cowboys games that season and four more in 1963 before leaving Dallas.

Dallas acquired defensive end Maury Youmans from Chicago in the 1964 offseason for wide receiver Gary Barnes. Youmans played all 28 Cowboys games across 1964-65, started 15 and recorded 6.5 sacks before his NFL career ended.

Chicago acquired tight end Austin Denney and kicker Mac Percival from Dallas for the 1968 No. 71 pick. Denney played 35 games with 32 starts for the Bears, while Percival spent seven seasons in Chicago and made 99 field goals, including 25 in a 100-point 1968 season. Dallas used the pick on Ed Harmon, whose NFL career lasted only 11 games, producing a decisive Bears win.

Dallas sent Craig Baynham and Phil Clark to Chicago during the 1970 draft for the Bears’ second-round pick, No. 27, used on tackle Bob Asher. Clark started at strong safety for Chicago in 1970, while Baynham added depth. Asher played only six games for Dallas, missed 1971 after knee surgery and was traded to Chicago in 1972. The realized value therefore favors the Bears, not Dallas.

Chicago Bears received 1972 seventh round pick (#182-Jim Osborne) in the exchange with Dallas Cowboys. The seventh-round choice became No. 182 Jim Osborne, who developed into a long-tenured Bears defensive lineman with substantially more starts and games than Caffey produced for Dallas. Against Dallas Cowboys' return of Lee Roy Caffey, that result supports a A- grade. The transaction is judged as Chicago Bears Win, with the mark based on the football value that actually followed from the deal.

Dallas acquired the rights to quarterback Jack Concannon from Chicago on August 17, 1972 and sent Bill Line, Bob Asher and a 1973 second-round pick to the Bears. Concannon never appeared in a Cowboys regular-season game. Asher immediately became a multi-year Chicago starter, Line started on the 1972 defensive front, and pick No. 48 produced Gary Hrivnak. Chicago won the exchange decisively.

The Bears' Bruce Craft purchase was inexpensive enough that the miss did little damage, but it was still a miss. Chicago surrendered $100 and did not receive meaningful regular-season production in return. Dallas' gain was equally small, yet it was tangible, so the Cowboys get the better grade without treating the transaction as more important than it was.

On 1974-08-10, Chicago Bears received Henry Youssef-Ahmadabadi / Henry Abadi, while Dallas Cowboys received draft pick (selection not identified). The hindsight verdict is Chicago Bears Win, with Chicago Bears graded B and Dallas Cowboys graded C. The evaluation follows the documented consideration and the football value that can be traced from it, while keeping unverified downstream pick identities or conditional outcomes out of the final judgment.

Chicago acquired wide receiver Golden Richards from Dallas and received immediate starting production. Richards started 14 games in 1978, catching 27 passes for 379 yards, then added 107 yards and a touchdown in five games during 1979. Dallas received two draft choices, but their combined direct contribution did not match Richards's short-term Bears role.

Dallas sent Jay Saldi to Chicago and received the 1984 sixth-round pick at No. 152, which became linebacker Eugene Lockhart. Saldi gave the Bears 28 games and 13 starts over 1983-84, with 21 receptions for 209 yards. Lockhart became a seven-season Dallas mainstay, playing 104 games with 96 starts from 1984 through 1990 and producing 16 sacks and six interceptions in his Cowboys tenure. Chicago got useful short-term depth; Dallas found a long-term defensive starter.

Dallas and Chicago exchanged five players plus a future sixth-round pick on August 17, 1993. The Cowboys received Kelly Blackwell, Markus Paul and John Roper; the Bears received Vinson Smith, Barry Minter and the 1995 pick that became Carl Reeves. Dallas quickly moved on from all three incoming players, while Smith became a regular Chicago linebacker for four seasons. Even Jimmy Johnson later acknowledged Chicago had gotten the better of the swap.

Chicago Bears received 1996 6th round pick (201st overall subsequently traded, Hayward Clay) in the 1994-08-28 exchange with Dallas Cowboys. Chicago used the acquired No. 201 choice as one piece of a larger move from No. 18 to No. 13, where the Bears selected Walt Harris. Against Dallas Cowboys' return of Jim Schwantz, that outcome supports a B grade. The transaction is judged Chicago Bears Win, with the mark tied to the football value that actually followed from the deal.

Dallas moved up in the 2002 draft for No. 63 Antonio Bryant and No. 129 Jamar Martin, sending Chicago Nos. 72 Roosevelt Williams, 104 Alex Brown and 140 Bobby Gray. Bryant had a productive NFL career, but Brown became a long-term Bears defensive starter and the best team-specific return in the deal. Chicago owns the edge.