While Charles Oakley's best playing performances are clearly behind him, he still would bring the Cavaliers two things they are lacking. First, Oakley played in the playoffs almost every year in his career (basically every year until the end of his career). He played for winners year-in and year-out. Although he lost in his only NBA Finals appearance, his Knicks team played in one of the most competitive finals in league history. Until last season, only Eric Snow had played in the Finals. Many of his teammates had not seen much playoff time and relied on collegiate experience. And, until last year, LeBron's championship stories always included St. Vincent-St. Mary high school memories of Dru Joyce hitting threes or Romeo Travis stepping up big.
Second, Oakley is a tough big man. Sure, all the big men the Cavs have under contract right now are tough in some way (Ilgauskas - surviving injuries and showing tolerance for pain; Gooden - playing through criticism; Varejao - bodying up on D; Marshall - finding ways to get up his shot), but Oakley is, in every aspect of his game, tough. More than anyone, Gooden would benefit from Oakley's presence. Gooden has arguably declined in performance in each year that the Cavs have had him. Bringing Oakley in would help Gooden get back to the basics at power forward.
Second, Oakley is a tough big man. Sure, all the big men the Cavs have under contract right now are tough in some way (Ilgauskas - surviving injuries and showing tolerance for pain; Gooden - playing through criticism; Varejao - bodying up on D; Marshall - finding ways to get up his shot), but Oakley is, in every aspect of his game, tough. More than anyone, Gooden would benefit from Oakley's presence. Gooden has arguably declined in performance in each year that the Cavs have had him. Bringing Oakley in would help Gooden get back to the basics at power forward.