The biggest problem with the front office is that it keeps think its better than what it really is:
1. The Wizards stuck with the core of Gilbert Arenas, Caron Butler and Antawn Jamison for far too long. This team was one and done group that Ernie Grunfeld and the FO continued to think it was better than that. The biggest example was in the 2007 season, when the Wizards had the best record in the East, Eddie Jordan coached the All-Star Game in Vegas, the FO developed a point of view that the team was a contender in the East despite the Eastern Conference being an incredibly inferior conference. When other teams like Boston, Miami and Cleveland (at the time) got better, the Wizards stubbornly continue to believe the they were the best team in the East when they were all healthy.
2. The second example was in 2009. The team had come off a season where Arenas missed a vast majority of the year to injuries. Instead of reaching for the dynamite, the Wizards decided to be short-sighted and to deal the 5th pick (rights to Ricky Rubio) for Mike Miller and Randy Foye. That did not make any difference and the Wizards sled to one of the worst records in the NBA regardless.
3. Another short-sighted swap, this time of Rashard Lewis' partially guaranteed contract and the 46th pick for Emeka Okafor and Trevor Ariza. The FO once again decided this move would be in there best interest as it supposedly gave the team a veteran presence. But Ariza and Okafor were due north of 22M per year over the next two years. Neither player addressed the team glaring weakness of perimter shooting. In fact Okafor was especially superfluous. The team had a pair of young, solid developing big man in Kevin Seraphin and Trevor Booker. There were many other better options the team could have went for instead of clogging their flexibility with Okafor and Ariza, even if they wanted to bring in "veteran presence" in the form of making an amnesty bid on Brand, participating in the 3 team deal for Dorrell Wright. Either player was cheaper and just a one year contract. You could have spent just $5M for that duo instead of north of $44M for the Okafor-Ariza duo. But I digress....
The funny thing is after this debacle of a deal, the Wizards are probably stuck in no better than mediocrity. John Wall remains the team one saving grace and promise for a better future. However when the team rids of itself of Okafor and Ariza, Wall's presumably double million extension will kick in, along with Okafor's contract. It's hard to see how the Wizards will get significantly better. At the rate the Wizards will go, their ceiling is likely no higher than the 8th seed if everything shakes out right. And in 6 years the Wizards will probably be dealing with the distraction of whether Wall will bail DC for greener pastures elsewhere.
That is the picture Ernie and the front office has painted of this franchise. It's not going to get much better. This year is already completely lost and its all about pride at this point in the year... a far cry of what many fans like myself expected when the season was set to tip off.