Cleveland acquired Lee Nailon and 2006 second round pick (#42-Daniel Gibson) for 2006 conditional second round pick (if Cavaliers finish with at least third best record in the league) (not exercised), producing a clear Cavaliers win on realized player, draft and roster value.
On February 23, 2006, Cleveland acquired Lee Nailon and Philadelphia’s 2006 second-round pick in exchange for a conditional Cavaliers second. The condition required Cleveland to finish with one of the league’s top records, so the outgoing pick never conveyed. Nailon did not become the point of the deal for Cleveland; the meaningful asset was the incoming second that reached the draft four months later.
Cleveland used the No. 42 selection on Daniel Gibson. He spent his entire seven-season NBA career with the Cavaliers, appearing in 397 regular-season games and adding valuable playoff shooting to the first LeBron James era. His signature early moment came in the 2007 Eastern Conference finals, when he scored 31 points in the clinching Game 6 against Detroit to help send Cleveland to its first NBA Finals.
The 76ers moved Nailon and a real second-round pick but did not receive an NBA player or a later draft selection from the conditional return. Because the Cavaliers did not meet the trigger, the promised second was never exercised. That makes the completed value unusually simple: Philadelphia surrendered the pick that became a long-term Cleveland guard, while the Sixers’ incoming asset expired without producing team value.
The obligation Philadelphia received depended on Cleveland finishing with at least the league's third-best record, according to the transaction terms. That condition was not satisfied, so it never became a pick the 76ers could select or trade on draft night. By contrast, the second Philadelphia sent was an actual 2006 draft asset, and Cleveland used it at No. 42 to take Daniel Gibson. This distinction explains the unusual grade disparity without having to imagine a missing Philadelphia player. Nailon was the veteran attached to the transfer, but the Cavaliers' long-term return came from the converted selection rather than his playing time. Gibson's 397 Cleveland regular-season appearances and the 2007 Eastern Conference finals performance are completed value; an unexercised conditional pick has no comparable player result to measure.
Cavaliers Win — Cleveland A+, Philadelphia D+. The No. 42 pick became Daniel Gibson, a seven-year Cavalier and an important shooter on the 2007 Finals team. Philadelphia’s conditional second never conveyed, leaving the Sixers without a comparable realized return. The transaction was small on trade day but produced a clear long-term Cleveland win once the draft pick converted.