Chicago Bears A+
Pittsburgh Steelers D
Chicago Bears received
- 1939 first round pick (#2-Sid Luckman)
Pittsburgh Steelers received
- Edgar Manske / Ed Manske / Eggs Manske
Chicago sent end Edgar 'Eggs' Manske to Pittsburgh in 1938 and received the Steelers' 1939 first-round choice. Pittsburgh finished with a pick that landed second overall, and the Bears used it on Sid Luckman. Luckman became a Hall of Fame quarterback and led Chicago to four NFL championships. Manske later returned to the Bears, making the first-round acquisition one of the most productive trades in franchise history.
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→ Chicago Bears B-
Pittsburgh Steelers C
Chicago Bears received
- rights to Bill Patterson / Billy Patterson
Pittsburgh Steelers received
Chicago acquired the rights to Bill Patterson, who reported and provided meaningful backfield and passing work during the 1939 season. His Bears contribution was not a long-term centerpiece, but it gave Chicago immediate offensive utility from the exchange. Compared with Sam Francis' brief five-game Pittsburgh tenure before another move, Patterson's larger role gives the Bears a modest advantage.
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→ Chicago Bears A
Pittsburgh Steelers D+
Chicago Bears received
- 1941 first round pick (#3-Norm Standlee)
Pittsburgh Steelers received
- Bill Patterson / Billy Patterson
Chicago obtained Pittsburgh's 1941 first-round selection in exchange for quarterback Billy Patterson. The pick landed third overall and became Norm Standlee, who joined a powerful Bears roster and contributed during the club's championship period. Chicago turned one outgoing veteran into a premium selection and a high-level back, while Patterson did not create comparable long-term value in Pittsburgh. The draft-capital conversion makes this a clear Bears victory.
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→ Trade 4
December 31, 1947
Chicago Bears Win Chicago Bears A
Pittsburgh Steelers C
Pittsburgh Steelers received
Chicago acquired the rights to Bobby Layne from Pittsburgh after the Steelers used the third overall choice in the 1948 draft on the Texas quarterback. The Bears gave up the rights to Ray Evans. Layne spent only one season in Chicago, but the Bears later moved him for two first-round choices, extending the value of the asset. Evans had one productive Pittsburgh season, so Chicago wins without making Pittsburgh's return worthless.
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→ Chicago Bears B
Pittsburgh Steelers D+
Pittsburgh Steelers received
- Fred Hartman
- rights to Walt Pupa
Chicago received Paul Stenn and turned the deal into four seasons of service. Stenn played 47 games and made 32 starts for the Bears from 1948 through 1951, giving Chicago durable value from a modest transaction. That sustained contribution clearly exceeded what Pittsburgh realized from Fred Hartman and the rights to Walt Pupa.
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→ Trade 6
September 24, 1949
Pittsburgh Steelers Win Chicago Bears D
Pittsburgh Steelers B-
Chicago Bears received
- 1950 fourth round pick (#48-Tom Novak)
Pittsburgh Steelers received
Chicago received Pittsburgh's 1950 fourth-round pick, No. 48 overall, and used it on Tom Novak. Novak never played an NFL regular-season game for the Bears. Pittsburgh, meanwhile, received 12 games and seven starts from Frank Minini in 1949. The Bears therefore converted the outgoing player into draft capital, but the selected player did not produce a regular-season return.
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→ Chicago Bears A
Pittsburgh Steelers D
Chicago Bears received
- 1952 eighth-round pick (#90-Bill Bishop)
Pittsburgh Steelers received
Pittsburgh acquired rookie end Tom Jelley from Chicago for the Steelers' 1952 eighth-round pick. Jelley appeared in five games without a start for Pittsburgh in 1951 and never played another NFL season.
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→ Trade 8
September 24, 1951
Chicago Bears Win Chicago Bears A-
Pittsburgh Steelers D+
Chicago Bears received
- 1952 fifth round pick (#54-Jack Hoffman)
Pittsburgh Steelers received
Chicago Bears received 1952 fifth round pick (#54-Jack Hoffman) in the exchange with Pittsburgh Steelers. Chicago's fifth-round choice became Jack Hoffman, who played 55 games with 54 starts for the Bears from 1952 through 1958. The supported hindsight grade is A-. That mark reflects realized value tied directly to this transaction, with the overall result recorded as Chicago Bears Win.
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→ Chicago Bears C
Pittsburgh Steelers B
Pittsburgh Steelers received
Chicago Bears received Jerry Shipkey. Chicago received Jerry Shipkey and got eight games of 1953 service. That was legitimate short-term roster value, but it did not match the immediate defensive impact Pittsburgh received from DeCarlo. Shipkey's Bears return was useful rather than transformative. The return was measurable, but it did not develop into a major long-term advantage for the acquiring club.
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→ Trade 10
September 16, 1957
Pittsburgh Steelers Win Chicago Bears C
Pittsburgh Steelers B-
Chicago Bears received
- cash
- draft pick (undisclosed overall/player)
Pittsburgh Steelers received
- Aubrey Rozzell
- Harland Carl
Chicago Bears received cash and draft pick (undisclosed overall/player) in the deal with Pittsburgh Steelers. Chicago received cash plus a draft choice whose exact downstream identity is not established in the surviving record. That still represented usable compensation, but there is not enough verified downstream value to outweigh Pittsburgh's known contribution. That outcome supports a C for Chicago Bears. The Pittsburgh Steelers Win verdict weighs documented games, starts, production and connected draft value.
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→ Chicago Bears B
Pittsburgh Steelers C+
Chicago Bears received
- 1963 first round pick (#11-Dave Behrman)
Pittsburgh Steelers received
Chicago sent quarterback Rudy Bukich to Pittsburgh on August 31, 1960 for the Steelers' 1963 first-round selection, later No. 11 overall. Bukich gave Pittsburgh two seasons of quarterback depth and some starting work, while Chicago controlled a premium future asset. The Bears later reacquired Bukich in a separate 1962 transaction, but the 1960 exchange itself still favored Chicago's first-round return.
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→ Chicago Bears D
Pittsburgh Steelers C
Chicago Bears received
- 1962 second round pick (#20-Clyde Brock)
Pittsburgh Steelers received
- Bob Coronado / Bobby Coronado
Pittsburgh acquired receiver Bob “Bobby” Coronado from Chicago on August 18, 1961, for the Bears’ eventual 1962 second-round choice, No. 20 overall. Coronado gave the Steelers five games, two starts, three catches and 32 receiving yards. Chicago used the pick on tackle Clyde Brock, but waived him before the 1962 season; he never played a regular-season game for the Bears. Pittsburgh wins a low-impact deal.
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→ Chicago Bears A
Pittsburgh Steelers D
Pittsburgh Steelers received
- 1963 tenth round pick (#137-Ed Hoerster)
Chicago Bears received Bobby Joe Green in the exchange with Pittsburgh Steelers. Bobby Joe Green spent twelve seasons with the Bears and served as their primary punter through a long tenure that included Chicago's 1963 championship season. Against Pittsburgh Steelers' return of 1963 tenth round pick (#137-Ed Hoerster), 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.
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→ Chicago Bears B+
Pittsburgh Steelers B
Chicago Bears received
- Rudy Bukich
- 1963 tenth round pick (#137-Ed Hoerster)
- 1963 first round pick (#11-Dave Behrman)
- 1964 second round pick (#23-Pat Crain)
Pittsburgh Steelers received
- 1963 first round pick (#11-Dave Behrman)
- Ed Brown (b)
Chicago and Pittsburgh completed two linked April 4, 1962 transactions involving the same 1963 first-round selection. Pittsburgh first returned that No. 11 choice to Chicago for Rudy Bukich and a tenth-rounder, then reacquired it along with a 1964 second-round pick for quarterback Ed Brown. Both quarterbacks later started for their new clubs, but Chicago’s added second-round asset gives the Bears a narrow win.
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→ Chicago Bears B+
Pittsburgh Steelers D+
Chicago Bears received
- 1963 4th round pick (52nd overall, Charley Mitchell)
- 1964 4th round pick (51st overall, later traded back to Pittsburgh)
Pittsburgh Steelers received
Pittsburgh acquired former star receiver Harlon Hill from Chicago for fourth-round picks in 1963 and 1964. Hill's peak had already passed; he caught only seven passes for 101 yards in seven games for the Steelers before finishing the 1962 season in Detroit. Chicago received two future selections, and the 1964 pick later became part of another Bears-Steelers deal tied to the 1965 first-round selection used on Dick Butkus. The direct trade strongly favored Chicago.
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→ Trade 16
September 6, 1962
Chicago Bears Win Chicago Bears B+
Pittsburgh Steelers C
Chicago Bears received
- 1963 sixth round pick (#80-John Johnson (Howard))
Pittsburgh Steelers received
Chicago Bears received 1963 sixth round pick (#80-John Johnson (Howard)) in the exchange with Pittsburgh Steelers. Chicago used the acquired sixth-rounder on John Johnson, who became a six-season Bears defensive lineman and supplied far more sustained value. Against Pittsburgh Steelers' return of Ken Kirk, that outcome supports a B+ grade. The transaction is judged as Chicago Bears Win, with the mark based on the football value that actually followed from the deal.
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→ Chicago Bears B+
Pittsburgh Steelers C+
Pittsburgh Steelers received
- 1964 sixth round pick (#84-Jimmy Jones)
Chicago Bears received Tom Bettis. The locked Wave 209 research supports the B+ grade after comparing the direct production and draft value attributable to this transaction. The evaluation excludes unrelated later moves and unsupported assumptions. Against Pittsburgh Steelers, that documented return supports the final verdict of Chicago Bears Win.
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→ Trade 18
September 10, 1963
Chicago Bears Win Chicago Bears B+
Pittsburgh Steelers C
Chicago Bears received
- 1964 sixth round pick (#84-Jimmy Jones)
Pittsburgh Steelers received
Chicago Bears received 1964 sixth round pick (#84-Jimmy Jones) in the exchange with Pittsburgh Steelers. The sixth-round choice became No. 84 Jimmy Jones, who developed into a multi-year NFL contributor with substantially more Chicago starts and games than Anderson produced in Pittsburgh. Against Pittsburgh Steelers' return of Art Anderson (a), that result supports a B+ grade. The transaction is judged as Chicago Bears Win, with the mark based on the football value that actually followed from the deal.
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→ Trade 19
December 2, 1963
Chicago Bears Win Chicago Bears A+
Pittsburgh Steelers C+
Chicago Bears received
- 1965 first round pick (#3-Dick Butkus)
Pittsburgh Steelers received
- 1964 second round pick (#28-Jim Kelly (Harry))
- 1964 fourth round pick (#51-Ben McGee)
Chicago sent Pittsburgh 1964 second- and fourth-round selections for the Steelers' 1965 first-round pick. Pittsburgh used its two choices on Jim Kelly and Ben McGee, with McGee becoming a two-time Pro Bowler and nine-season Steeler. Chicago's acquired first-rounder landed third overall and became Dick Butkus, whose Hall of Fame career gave the Bears the exchange's defining player.
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→ Trade 20
September 3, 1964
Chicago Bears Win Chicago Bears A-
Pittsburgh Steelers D
Chicago Bears received
- 1966 fourth round pick (#51-Randy Jackson (Belford))
Pittsburgh Steelers received
Chicago sent Chuck Logan to Pittsburgh and received the 1966 fourth-round pick that became No. 51 Randy Jackson. Jackson developed into an eight-year Bears offensive lineman, appearing in 105 games and starting 94. Logan gave Pittsburgh one season, one catch, and seven receiving yards. Turning a lightly productive player into a long-term starter makes this one of the clearest wins in the batch.
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→ Chicago Bears C
Pittsburgh Steelers C
Pittsburgh Steelers received
- Charlie Bivins / Charley Bivins
Pittsburgh and Chicago swapped Charlie Bivins and Dan James on August 28, 1967. Neither veteran created meaningful long-term value for his new club. Bivins appeared in only two games for Pittsburgh before finishing the season with Buffalo, while James played two games for Chicago and then retired. With the package confirmed but both returns extremely short-lived, an even C/C result fits the outcome.
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→ Chicago Bears C-
Pittsburgh Steelers A-
Pittsburgh Steelers received
- 1976 second round pick (#37-Ray Pinney)
- 1977 fourth round pick (#99-Laverne Smith)
Pittsburgh sent veteran receiver Ron Shanklin to Chicago for a 1976 second-round choice and a 1977 fourth-round choice. The Steelers used those selections on tackle Ray Pinney and running back Laverne Smith. Pinney became the prize, playing 125 games with 82 starts and starting in a Super Bowl victory, giving Pittsburgh a decisive long-term return.
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→ Trade 23
September 5, 1978
Pittsburgh Steelers Win Chicago Bears C
Pittsburgh Steelers C+
Chicago Bears received
- past considerations (unspecified; procedural waiver workaround)
Pittsburgh Steelers received
Pittsburgh reacquired running back Alvin Maxson from Chicago on September 5, 1978 for unspecified past considerations. The transaction was a waiver-workaround arrangement: Chicago had signed Maxson days earlier and sent him back to Pittsburgh before he ever traveled to join the Bears.
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→ Trade 24
October 19, 1993
Pittsburgh Steelers Win Chicago Bears B-
Pittsburgh Steelers B+
Pittsburgh Steelers received
- 1994 fifth-round pick (No. 140, Myron Bell)
- 1995 conditional late-round pick (not conveyed)
Pittsburgh traded running back Tim Worley to Chicago on October 19, 1993, for conditional draft compensation. The realized 1994 choice became No. 140, safety Myron Bell, while the later 1995 condition was not exercised. Worley gave Chicago 437 rushing yards in ten 1993 games, but Bell's six Pittsburgh seasons and 80 appearances ultimately created more durable value.
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→ Chicago Bears B-
Pittsburgh Steelers B-
Pittsburgh Steelers received
- 1995 5th round pick (151st overall, Lee Flowers)
Chicago Bears received Jeff Graham in the 1994-04-29 exchange with Pittsburgh Steelers. Pittsburgh sent Jeff Graham to Chicago for the future fifth-round choice used on Lee Flowers. Graham immediately became a major Bears receiving piece, including a 1,301-yard season in 1995, while Flowers developed into a long-tenured Steelers defensive back and starter. The documented result supports a B- grade for Chicago Bears. The overall verdict is Even Trade, based on realized value rather than hypothetical upside.
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→ Trade 26
November 1, 2022
Pittsburgh Steelers Win Chicago Bears F
Pittsburgh Steelers A+
Pittsburgh Steelers received
- 2023 2nd round pick (32nd overall, Joey Porter)
Pittsburgh traded Chase Claypool to Chicago for the Bears' 2023 second-round pick, which finished No. 32 overall and became Joey Porter Jr. Claypool played only 10 games for Chicago, catching 18 passes for 191 yards and one touchdown before the Bears traded him to Miami. Porter has started 41 games through three seasons with 31 passes defensed and three interceptions. The trade became a franchise-level win for Pittsburgh.
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→ Chicago Bears A-
Pittsburgh Steelers B+
Chicago Bears received
- 2025 sixth-round pick, No. 202 overall, later traded to the Rams for Jonah Jackson
Pittsburgh Steelers received
Pittsburgh acquired Justin Fields for a conditional 2025 sixth-round pick that remained a sixth and became No. 202 overall. Fields gave the Steelers a useful one-year bridge, going 4-2 in six starts and finishing 2024 with 1,106 passing yards, 289 rushing yards and 10 total touchdowns. Chicago later used the No. 202 pick to acquire guard Jonah Jackson from the Rams. Jackson started all 17 games for the 2025 Bears and remained a starter entering 2026, giving Chicago the stronger realized downstream return to date.
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