One of my two votes went towards hiring Paxson for GM and I'll go further into detail. It should be a top two choice on here.
Jim Paxson was a solid shooting guard for the Blazers for about a decade, went to two AS games. He and his more decorated brother grew up in Ohio and started at U of Dayton. Sounds like a feel good story, until it wasn't.
Named GM in 1999 after an internship of a year under Embry, he did a little good and a lot of bad. Mind you that Embry left him some quality young players like DA, Sura, Wes Person, Brevin Knight, Big Z... many would go on to very successful careers elsewhere after Paxson traded them away. An argument could easily be made that hiring a cadaver propped up in a chair would have fielded a better team by doing nothing.
Year one: Trading Potapenko for DeClerq and a first rounder that became Miller worked out because the Celtics didn't know The Ukraine Train was battling a drinking problem. That same year, he drafted Trajon Langdon in the lottery and let local kid and fan favorite Earl Boykins walk after a surprising rookie year. Langdon became a Euroleague star and Boykins would go on to score almost 5,800 points with over 2,000 assists coming off NBA benches as instant offense. The next year he shipped out Bob Sura (5,000+ points 2,000+ rebounds, 2,000+ assists career) and Derek Anderson (almost 7,000+ points, 2,000 rebounds, 2,000+ assists career) for Tractor Traylor and Lamond Murray, followed by drafting and trading 19,000+ point career scorer Jamal Crawford for Chris Mihm. The second rounder sucked. Lots of fail.
So again, to his credit in 2000 he traded DeClerq for Matt Harpring, which was a solid move. He did get out from under the Shawn Kemp contract for expiring deals, leading to a crazy season full of mercenaries who had no plan on sticking with the franchise. Now the negatives: traded away Brevin Knight and his career 4,400+ assists and 1,200+ steals for the ghost of Jim Jackson, drafted Saggy Diop, and traded Brendan Haywood's draft rights for Micheal Doleac. Haywood had over 1,100 career blocks and nearly 4,900 career rebounds playing for contenders year after year. As per usual, the second rounder sucked. Locked down Bimbo Cole's to play point guard rather than those quality guards I mentioned he moved the past two years.
We now see lots of talented young players traded for aging vets and chances taken on bad young players heading into 2002. He doubles down by trading solid young forward Harpring for aging Tyrone Hill and stretch four Jumaine Jones. He also manages to lock down Ricky Davis in a trade for one of those aging veterans who doesn't like to play for the franchise, Chris Gatling. This is important because it's one of the few good trades in his tenure. In the draft he takes Dajuan Wagner in the lottery to prove yet again he can't find any guard who could have a better career than undrafted local kid Earl Boykins no matter how many assets he blows through. But finally, a second rounder doesn't suck: Future All Star Carlos Boozer. Maybe he is learning. He isn't. He trades Wes Person (career 8,100+ points, 2,400+ rebounds, 1,200+ assists) for the ghost of Nick Anderson who retires and Matt Barnes, who also never plays a minute for the Cavs. He spends the next season dumping good players left and right, including his only good 1st round draft pick in Andre Miller, for what amounts to Darius Miles and a series of failed experiments like Smush Parker. He moves the frustrated Lamond Murray for Micheal "Yogi" Stewart and the first rounder who would become Jared Dudley... but that pick will be wasted soon. At this point the face of the franchise is still Big Z on one bad foot carrying all these scrubs.
After lucking into LeBron James in the most important lottery in draft history, they select Jason Kapono ahead of players like Kyle Korver and Luke Walton. The mistakes of the 2003-2006 Cavs until Paxson is finally fired are well-documented: Kevin Ollie, Ira Newble, JR Bremer, Kedrick Brown, Eric Williams, Ruben Boumtje-Boumtje, Jeff McInnis, Eric Snow, Sasha Pavlovic, Luke Jackson, Drew Gooden, Steven Hunter, Jiri Welsch... all these scrubs cost actual assets or valuable cap space. Few had a better career than the 5'5 local kid he didn't bother to resign in his first year running the team. Sure we occasionally grabbed Varejao or Tony Battie to cloud the situation, but it was a whole truckload of fail that led to LeBron eventually leaving in disgust.
Jim Paxson, destroyer of a fairly talented young core Embry set up for him and poisoner of everything Danny Ferry tried to fix. One of the main causes of me writing about the Cavs and why they frustrate me daily, which carries through every fiber of my being today. As dark a stain as any on the history of the Cleveland Cavaliers.