On this day in 1987: The Bulls sign Scottie Pippen

Thirty-nine years ago today, on Wednesday morning, October 14, 1987, the Chicago Bulls signed Scottie Pippen to his rookie contract — the deal that turned a draft-day trade with Seattle into a roster reality. UPI’s transactions wire that same day listed it plainly, misspelling and all: “Chicago — Signed forward Scott Pippin.” The Chicago Tribune’s next-day report filled in the stakes: a unique six-year package worth more than $5 million, engineered by agent Jimmy Sexton with owner Jerry Reinsdorf and general manager Jerry Krause, while coach Doug Collins prepared to throw the Arkansas product into a small-forward battle with Brad Sellers.

Michael Jordan and Charles Oakley welcome Scottie Pippen to the Chicago Bulls in an NBA Live 2004 Dynasty Cutscene.

On this day in 1987, the Bulls signed Pip, having acquired him from the Seattle SuperSonics in exchange for fellow rookie Olden Polynice during the Draft in June. pic.twitter.com/VfA4VowRUu

— NLSC (@TheNLSC) October 14, 2026

The June deal that made Oct. 14 possible

None of that Wednesday morning paperwork happens without draft night. On June 22, 1987, the Seattle SuperSonics selected Pippen fifth overall. The Bulls took Olden Polynice eighth, then flipped the board: Chicago sent Polynice, a 1988 second-round pick, and a 1989 first-rounder (the pick that became B.J. Armstrong) to Seattle for Pippen and a 1989 first (Jeff Sanders). The trade locked Pippen into Chicago’s plans before he ever put pen to paper — and October 14 was when the contract finally closed the loop.

A unique six-year contract

Chicago Tribune reporting the morning after the signing described a structure that stood out even by 1980s standards. The package ran more than $5 million over six years — four guaranteed, plus two club options — with deferred money earning interest. Pippen’s first-year salary sat a little under Michael Jordan’s roughly $830,000. A $50,000 Rookie of the Year bonus clause was written in. Sexton handled the player side; Reinsdorf and Krause closed it for the franchise.

Pippen told reporters he planned to buy his mother a house and a car. At his first Bulls practice he was the second player on the floor. Collins noted that Pippen had missed nine practices and was on a crash course; Sellers was still competing for the small-forward minutes. That night Chicago cut Anthony Wilson to keep the roster at 15. The signature was not a ceremonial afterthought — it was the day Pippen officially joined the fight for a job.

Why the signature still echoes

The rookie year that followed was modest by later Pippen standards: 79 games, 7.9 points per game mostly off the bench in 1987-88. What October 14 locked in was the long arc. Pippen went on to win six championships with Jordan’s Bulls, earn Hall of Fame honors, and see his No. 33 retired on December 9, 2005. The Sonics had the fifth pick; the Bulls had the trade and, on this Wednesday morning 39 years ago, the contract.

On this day in franchise history, the paperwork mattered as much as the draft board. Seattle selected Pippen. Chicago signed him. Everything that followed — the sidekick who became a cornerstone, the six titles, the retired jersey — traces back to a morning when UPI typed the wrong spelling and the Tribune explained why the deal was unlike anything the Bulls had offered a rookie before.