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Throughout the 1999-2000 season, the Jazz won the Midwest Division but one time again struggled in the postseason, behind to the Portland Trail Blazers, again throughout the second round. Throughout the offseason, Jeff Hornacek retired and Howard Eisley was traded in a four-team contract that brought in Donyell Marshall. The Jazz selected promising high school basketball star DeShawn Stevenson in the primary round of the NBA Draft. In the 2000-2001 season, Jazz went 53-29, but their playoff woes one time again struck when Jazz blew a 2-0 series lead in the first round of the playoffs to the Dallas Mavericks.
In the 2001-2002 season, Andrei Kirilenko made his recruit debut, but overall the Jazz started to show their age and declining talent. The Jazz finished just 44-38 and lost to the Sacramento Kings 3-1 in the primary round of the playoffs. In 2002-2003, Donyell Marshall and Bryon Russell moved on to additional teams. Matt Harpring , though, was brought over from the Philadelphia 76ers, causal to the offense and experiencing his best season. The Jazz barely scraped during into the playoffs, going 47-35 and over losing to the Sacramento Kings 4-1. After the season, the end of an era came when John Stockton retired and Karl Malone moved to the Los Angeles Lakers in the chase for a championship ring with three other future Hall-of-Famers. The Lakers were compressed in the Finals.
In the 2003-2004 season, the Utah Jazz were predictable to be one of the weakest teams in the NBA, but in its place they very much exceeded most analysts' expectations. The Jazz team featured more than a few unheralded players who emerged into key contributor, including Andrei Kirilenko , Raja Bell, Matt Harpring , and Carlos Arroyo . In exacting, Andrei Kirilenko demonstrated tremendous adaptability on both offense and defense and earned a spot in the All-Star Game. Kirilenko helped the team late into the season's playoff hunt, in which the Jazz missed out by just one game to the Denver Nuggets, ending their streak of 20 successive seasons in the playoffs. Jerry Sloan over second in the voting for the NBA Coach of the Year Award, behind to Hubie Brown of the Memphis Grizzlies.
In the 2004 offseason, the Jazz obtain free agent Carlos Boozer (from the Cleveland Cavaliers) and Mehmet Okur (from the Detroit Pistons) and trade Ostertag to the Sacramento Kings. The permit was again predictable to contend in the West. The season started well for the Jazz, but a series of injuries, primary to Arroyo and Raul Lopez , and afterward to Boozer and Kirilenko, caused the Jazz team to fall to the base of the division. There were rumors of interior discontent between the younger players and Sloan , most important to the trading away of Arroyo mid-season to the Detroit Pistons in exchange for Elden Campbell (who was immediately waived). Jazz ended the 2004-2005 season with a record of 26-56, their most horrible since the 1981-1982 season.
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