I'm trying to catalog all of the Magic's misadventures under his tenure. Feel free to correct any mistakes or omissions.

• Drafting Vasquez over Granger & David Lee. For a team with holes everywhere, passing on a stud like Granger was unforgivable. Especially since he's a deadly 3-point shooter and big enough to play 4. Could have bypassed the entire Lewis-Arenas debacle with this move.
• Rashard Lewis for 100+ mil. Ultimately, it bit the team in the a$$, as we all knew it would, but it was a fun ride for a couple of years. What irks me, is that no one else was offering anywhere near what Otis paid. And he gave lewis the extra year a via sign and trade with the (then) sonics, in which the sonics got a ~9 mil trade exception. Presti then used the TE to get Kurt Thomas and two first rounds picks from Phoenix. He then flipped Thomas for two expiring contracts and another first round pick from the Spurs. Total haul: 3 first round picks, one of which became Serge Ibaka. Thats how you do it, create a rotation stalwart/possible all-star from nothing (or, in this case, the stupidity of Otis Smith).
  
• Trading a first round pick (which became Rodney Stuckey) to run the Darko experiment. Not a bad move at the time--trading a mid first rounder for a big with a lot of talent--but its clear it was an unmitigated disaster, especially when Stuckey blew up against the Magic in the first round of the playoffs as a rookie.
• Trading for Rafer Alston instead of Kyle Lowry. To be fair, they did ride him to the nba finals and lowry was never much of a shooter. But he was then, and is certainly now, the better player. Since Hedo ran most of the offense anyway, all lowry needed to do was bring the ball upcourt and not turn it over. Also, skip shot awfully during his 29 game stint.
• Trading Gortat and VC for a one year rental on Jason Richardson & Turk's onerous contract. Lost a prime trade asset *and* got a horrible contract in return.
  
• The Duhon signing. This is a guy who was cited for public urination and spurned the magic a few years earlier when he signed with NY instead. Now he's imploding offensive possessions for the Magic.
  
• The Q-Rich signing. Nice guy, plays hard but he's also carrying a spare tire around his waist and was 3 years past being effective when Otis signed him.
• Drafting Daniel Orton. He may not be a bust yet, but for a team in a win-now mode, it didnt make any sense to draft a major project center, when all you need is a stopgap for 10-12 mins a night. There is no scenario in which this move made sense for the Magic. Assuming he turns out to be a talented player, he's never going to develop that talent in Orlando, so you'll lose him in restricted FA when someone gives him crazy money. If he takes a while to develop, you've lost the immediate productivity you could have gotten from a 3-4 yr college player like Landry Fields (although the rest of the draft board below Orton was horrible). If he's a bust, well, thats self-explanatory. You can always try to roll over the pick to another year.
  
• Arenas! Bad knees, 100+ mil, threatened to shoot someone, twitter feed, black hole on offense, terribly inefficient even when he was good
• Trading Bass for Big Baby. No explanation needed.
  
• Resigning Richardson. No explanation needed.
  
• Waiting to move Dwight. If he says he's only interested in 3 teams, and those are the only ones willing to make serious bids, the offers are unlikely to improve before march. I forsee the Magic moving him in disgrace in late february for a much smaller haul than the 5 first rounders + Lopez + Hedo amnesty they passed on.
• Trading Trevor Ariza for Mo Evans and Brian Cook. Where to begin. After somehow wrangling Ariza in the Steve Francis trade, Otis goes ahead and moves him for a 3-point shooting big man (except he never shot well in Orlando, his defense was horrendous, and he perpetually looked like he'd been picked from a lineup at the local Y to meet the minimum dressed players requirement). Then there was Mo Evans, a serviceable 2 guard, except thats exactly what ariza was, except he was younger, more athletic and capable of guarding multiple positions. Of course, all this blew up spectacularly when Ariza torched the magic in the finals, in a series where two games were lost in overtime no less.
• Forgot to add: trading Drew Gooden and Anderson Varejao to cleveland for an aging Tony Battie. Great great locker room presence for a young dwight, but how on earth do you trade two young bigs for an old one? Battie also missed an entire year with a shoulder injury and was never the offensive player gooden was, nor the defensive player varejao became. Update: Weisbrod was calling the shots on this one.
• And lastly, how could I forget (seriously, I forgot in the original version of this post): The Stevie Franchise pu-pu platter. Though this was many years ago, I remember the Suns dangling a young Amare and picks and Weisbrod and company passing because they also wanted Joe Johnson, or something. So Weisbrod goes after Franchise because (and this is true), he saw Franchise cold-cock Amare when STAT dunked on Yao Ming and then started scowling at him. In that game franchise got ejected for the punch, the suns won in overtime and Amare tore up the stat sheet. And what weisbrod took away is 'I really need a hockey enforcer on my team.'
  

The last two were under weisbrod's tenure, but I know Otis figured prominently in the decision making as part of the Magic's 'brain trust'

Something that generally bothers me about Otis' deals is his inability to get a team option on the final year of a contract. Instead, he always makes it a player option, and even for mid-tier players like bass.