The Jones Signing Required a Draft-Pick Compensation Settlement
Portland signed veteran big man Caldwell Jones as a free agent in October 1985 after his spell with Chicago, sending the Bulls a 1987 second-round selection as compensation for relinquishing their matching rights. Historical ledgers disagree on the effective day: the Basketball-Reference team registers show October 1, while the detailed pick transaction chain uses October 9. That provenance difference is flagged for reconciliation without altering the archived date during an editorial-only repair. It was not an ordinary player-for-player swap. Portland obtained Jones's services directly, whereas Chicago received a future asset it could keep or trade before the 1987 draft.
Jones Played Four Useful Seasons for Portland
Jones gave the Trail Blazers a long run of frontcourt work after his signing. He appeared in 80 regular-season games in 1985-86, then 78 in 1986-87, 79 in 1987-88 and 72 in 1988-89, totaling 309 Portland games. The 1985-86 season included 19 starts and 355 rebounds, while 1987-88 brought 77 starts and 408 rebounds. By then Jones was a veteran role player rather than an offensive star, but Portland used him extensively enough for the signing to create real roster continuity. His previous Philadelphia and Chicago production is excluded from the Trail Blazers' acquired return.
Chicago Traded the Pick Back Before Milwaukee Selected Garland
The future second-rounder eventually became the No. 40 pick in 1987, but Chicago never drafted Winston Garland with it. On June 17, 1986, the Bulls returned that selection to Portland alongside the rights to Larry Krystkowiak and an additional 1992 second-round pick for Steve Colter. Colter appeared in 27 Bulls regular-season games in 1986-87 before leaving the club. Portland then moved the No. 40 selection to Milwaukee on November 11, 1986 for Chris Engler. The Bucks drafted Garland the following summer. His eventual 511-game NBA career does not belong to either original club's realized playing return from this compensation deal.
Portland Received the Stronger Direct Basketball Return
Portland paid a second-round selection and received 309 games from Jones. Chicago obtained a movable pick and used it as only one part of a larger three-asset transaction that brought Colter, so the Bulls have some traceable but limited downstream roster value. Crediting the entire Colter acquisition to this single selection would overlook the other assets Chicago surrendered. The source-supported outcome is more favorable to Portland than the inherited Even Trade verdict suggested, though Chicago did get real flexibility from the compensation. The mismatch between the original teams' draft rights and the eventual Bucks selection also makes it important not to invent Chicago minutes for Garland.
Final Verdict
Blazers Win. Portland earns A- for 309 games of Caldwell Jones frontcourt depth over four seasons. Chicago retains C+ for securing a second-round pick that helped form a larger package for Steve Colter, who played 27 Bulls games. Milwaukee eventually drafted Winston Garland, so his later NBA production is not credited to either original club.