Chicago Bears–Cleveland Browns Trade History

Chicago Bears received Harry Jagade / Chuck Jagade / Chick Jagade. Chicago received Harry Jagade, an established Cleveland back, but his Bears tenure did not create value comparable to the package sent to the Browns. His post-trade Chicago contribution was limited enough that it could not offset Cleveland's multi-asset return.

Chicago acquired defensive end Doug Atkins and safety Ken Gorgal from Cleveland before the 1955 season for third- and sixth-round picks in the 1956 draft. Cleveland used those selections on Larry Ross at No. 34 and Sherman Plunkett at No. 71. Atkins became a Hall of Famer and longtime Bears star, creating a major value advantage for Chicago.

Cleveland Browns received Jim Haluska; Chicago Bears received 1958 third-round pick No. 37, Don Healy. Haluska never appeared in a regular-season game for Cleveland after the trade. Healy played two full seasons for Chicago, appearing in 24 games with three starts before the 1960 expansion draft. The realized outcomes support Chicago Bears Win, with Cleveland Browns graded C and Chicago Bears graded B.

Cleveland traded receiver Rich Kreitling to Chicago in June 1964 for defensive back Lowell Caylor plus the Bears' 1965 second- and third-round picks, No. 17 Jim Garcia and No. 32 Bo Scott. Kreitling played only one final NFL season, while Scott became a productive multi-year Browns contributor. Cleveland turned an expendable veteran into three assets and earns an A to Chicago's C.

Cleveland sent receiver Eppie Barney to Chicago in September 1969 for the Bears’ 1971 sixth-round choice. The Browns used pick No. 142 on tackle Doug Dieken, who became a 14-season Cleveland fixture and started a remarkable run of 194 consecutive games at left tackle. Barney’s NFL career ended after limited production. Turning a marginal veteran into one of the franchise’s longest-serving linemen makes Cleveland the decisive winner.

On 1973-08-08, Chicago Bears received Randy Mattingly, while Cleveland Browns received 1974 tenth round pick (#238-Mike Puestow). The hindsight verdict is Even Trade, with Chicago Bears graded D and Cleveland Browns graded D. The evaluation follows the documented consideration and traceable football value, while leaving unresolved downstream pick identities out of the judgment.

Chicago's conditional return ultimately became the 1976 sixth-round pick used on Dan Jiggetts after Glen Holloway's NFL career ended with the 1974 season. Jiggetts then spent seven seasons with the Bears, appearing in 98 games as a reserve lineman. Cleveland received one season from Holloway: 14 games and three starts. The concrete outcomes support the existing B-to-C Bears win.

Cleveland traded quarterback Mike Phipps to Chicago on May 3, 1977 for a 1977 fourth-round pick and the Bears' 1978 first-round pick. The fourth-rounder became defensive tackle Mickey Sims, who played 43 games with 23 starts for Cleveland. The first-rounder landed at No. 20, which the Browns later sent to the Rams for No. 23 and a fourth-rounder. Cleveland used No. 23 on Hall of Fame tight end Ozzie Newsome.

Cleveland turned linebacker Bruce Huther into the 1983 seventh-round choice used on Rocky Belk. Huther appeared in only four games for Chicago in 1982, while Belk played 10 games for Cleveland in 1983 and caught five passes for 141 yards and two touchdowns. Neither return became a long-term piece, but the Browns extracted more measurable production from the exchange and deserve the modest hindsight edge.

Cleveland sent center Gerry Sullivan to Chicago on August 23, 1982, for the 1983 sixth-round pick that became No. 145 and Tim Stracka. Sullivan never appeared in a regular-season game for Chicago, while Stracka gave Cleveland 19 games, one start and two receptions for 27 yards across 1983-84. The Browns realized more on-field value and earn the win, C+ to D.

Chicago Bears received Andy Frederick from Cleveland Browns, while Cleveland Browns received past considerations (compensation for Gerry Sullivan retiring after being traded to Bears) in the 1983-04-27 deal. In hindsight, Chicago Bears produced the stronger realized return, which supports the higher grade on this side. The final grades are B for Chicago Bears and C for Cleveland Browns, producing a verdict of Chicago Bears Win. The rating reflects the documented package, the certainty of the consideration, and the football value that can actually be assigned in hindsight.

Cleveland acquired Chicago's first three selections in the 1984 supplemental draft of USFL and CFL players and turned them into Kevin Mack, Gerald McNeil and Doug West. Mack became a two-time Pro Bowl running back with 5,123 rushing yards for the Browns, and McNeil added return value. Chicago found a strong late-round contributor in Shaun Gayle, but Mack gave Cleveland the superior return.

Cleveland acquired veteran center Jay Hilgenberg from Chicago in August 1992 for a conditional 1993 pick tied to his performance. The condition settled as a fourth-rounder, No. 97, which the Bears used on Todd Perry. Hilgenberg offered Cleveland short-term line help, but Perry became a long-term Chicago starter, so the Bears earn a B+ while the Browns receive a respectable C+.

Chicago's direct return for No. 174 was No. 184 and No. 207, not No. 221. The Bears used No. 184 on Rashard Cook, then immediately sent No. 207 back to Cleveland for Nos. 221 and 253; none of those Chicago-controlled selections produced a Bears regular-season contributor. Cleveland used No. 174 on Marcus Spriggs, who played 18 games with two sacks.

Chicago sent picks Nos. 209 and 225 to Cleveland for three seventh-round choices. The Bears used No. 223 on James Cotton and No. 254 on Michael Green, while later moving No. 232 again. Green became the strongest direct player outcome in the exchange, giving Chicago useful long-term value from an otherwise late-round package.

Cleveland acquired offensive lineman Lennie Friedman from Chicago on August 24, 2006 for a conditional 2007 seventh-round draft choice. Friedman played all 32 regular-season games for Cleveland over 2006 and 2007, making two starts.

Cleveland traded defensive tackle Chris Williams and a 2025 seventh-round pick to Chicago on August 24, 2024 for a 2025 sixth-round pick originally acquired from Miami. Williams played 31 regular-season games for the Bears across 2024-25, recording 37 tackles and four sacks. Chicago later used the seventh-rounder, No. 240, as part of its 2025 draft trade with Buffalo, giving the Bears both direct defensive production and retained draft capital.

Chicago got eight games, 13 tackles and no sacks from Joe Tryon-Shoyinka in 2025, then used the acquired No. 239 pick with another seventh-rounder to move up for Jordan van den Berg, who made his 2026 debut in Week 1. Cleveland used No. 206 as one of three picks to move up for Austin Barber, now a rookie starter. Both draft branches are still too early for a stronger hindsight call, so C/C remains even.