Grunfeld has served as the president of basketball operations since then-majority Owner Abe Polin fired Michael Jordan from the role in 2003. Grunfeld now runs the show in Washington, and he has been in full control since he was re-signed to a multiyear extension on Oct. 5, 2006.
There's no doubting he brought the franchise some great years, particularly the always exciting and unpredictable Gilbert Arenas era of 2004-2008. DC's "big four" of Arenas, Antawn Jamison and equal parts Caron Butler and Larry Hughes brought four consecutive playoff appearances for the Wiz.
And in a testament to Grunfeld, all four were either signed or acquired via trade.
Though three former NBA draft selections received late-end and honorable mention rankings on this slideshow, the goal was to avoid draft selections when ranking Grunfeld's worst.
He has, after all, been known to make his trades interesting enough that no other material should be necessary.
Roger Mason Jr. went on to mildly successful stints in San Antonio and Miami
As promised, we begin with a few of the worst draft picks of Grunfeld's career. The Wizards have had their least success selecting players from overseas, as each player drafted on this list (except for Ramos) hailed from outside the United States.
13. Peter John Ramos (Puerto Rico), No. 32 overall pick in 2004 NBA draft
The skinny: The fourth pick of Grunfeld's career, Peter John Ramos appeared in six games for the Wizards.
12. Jan Vesely (Czech Republic), No. 6 overall pick in 2011 NBA draft
The skinny: Vesely shot a meager .308 percent from the free-throw line in 51 games during 2012-13.
11. Waiving Roger Mason Jr., Apr 26, 2010
The skinny: Fan favorite was shown the door after a finger injury ended his 2012 season.
Mason was a high character guy who would have helped keep the locker room together during its toughest times. Combined that leadership with his solid shot from three, he was good enough to keep around. This article by Bleacher Report Featured Columnist Grant Hughes aptly explains Mason's quality personality.
Date: June 28, 2006
Taken three picks ahead of Rajon Rondo, Pecherov had his best season for the Minnesota Timberwolves when he averaged 4.5 points per game.
Drafted out of Ukraine, Pecherov was the No. 18 overall pick in 2006 NBA draft.
While I see it as unfair to judge Grunfeld's draft selections as the worst transactions of his career, some are hard to ignore. Many of them do represent his worst decisions, but because the NBA draft can be so upside-oriented and overanalyzed, it is too easy to blame these selections on Grunfeld years after the fact.
Still, Pecherov over Rondo? Come on.
The presence of Gilbert Arenas at the point in 2006 certainly discouraged the Wizards from pursuing another player at the 1. Nonetheless, it is hard to not imagine Rondo being a dominant player in a Washington uniform.
But enough of Grunfeld's draft history. On to the real transactions.
Date: Feb. 14, 2010
In an expected move to rebuild the roster, the Wizards dealt Caron Butler, DeShawn Stevenson and Brendan Haywood for Josh Howard and Drew Gooden.
While it sounds like a fair trade, consider this.
Caron Butler had been averaging an impressive 18.9 points per game during his four-plus years with the Wizards. The mark is to this date his highest average with any team and more than three points above his career average of 15.5.
Howard, on the other hand, played just 22 games for the Wizards and ultimately was a disappointing addition to the team. The former Wake Forest star scored well and brought fans some excitement, but Howard has been on the downside of his career since coming to the Wizards.
Gooden was sent packing soon after the trade, a transaction that will be addressed shortly.
Date: Sept. 28, 2005
Ernie Grunfeld is not the only NBA executive to underestimate Steve Blake.
The point guard may not be a scoring machine, but he has served as a solid contributor off the bench for now 10 NBA seasons.
When Washington failed to match Portland's second-round tender to Blake, they were letting go of a solid backup point guard. With a 38 percent career average from three and a nearly four assists a game for his career, Blake has made an impact at every stop of his NBA livelihood.
It did not hurt the fans appreciation for Blake that he was a beloved Maryland Terrapin and the Wizards second-round pick in 2003.
Date: Feb 17, 2010
The effort to rebuild continued when the Wizards let go of their other most consistent player, Antawn Jamison, in the form of another trade.
Gooden was again involved, this time in a three-team trade including the the Los Angeles Clippers and Cleveland Cavaliers. The Clippers added Gooden, Cleveland got the scoring touch of Jamison as well as Shaun Livingston from L.A.
The Wizards got legendary Cavalier Zydrunas Ilgauskas, a promising young scorer at the 3 in Al Thornton and the Cavaliers' 2010 first-round pick. Once again, the Wizards sound like they did alright.
But they didn't.
Michael Lee of The Washington Post reported a week after the trade that the Wizards bought out Ilgauskas, effectively never allowing the 7'3'' monster to wear a Washington uniform.
After putting up 8.0 points a night in 49 contests for his new team, the Wizards bought out Al Thornton's contract on March 1, 2011. They attempted to replace him that summer by drafting fellow Florida State alum, the now-underachieving Chris Singleton.
As for the 2010 draft, the first-round pick acquired from Cleveland, No. 30 overall, was used to select Lazar Hayward, who was later traded to the Minnesota Timberwolves. Draft day trades with Minnesota may or may not be a point of foreshadowing.
Fortunately, the Wizards own draft pick was No. 1 overall pick John Wall, who has turned out pretty well.
Date: Sept. 24, 2010
Part of the issue with re-signing Blatche was that at the time, the move could be perceived as a statement from Grunfeld that Blatche was the most valuable player on the team.
That during the 2010 offseason, the Wizards emphasized rebuilding is a moot point at this juncture. During the 2010-11 season, his first under the new contract, Blatche scored and rebounded well, averaging 16.8 and 8.2 in both categories, respectively. Given those numbers, the five-year, $35 million contract offered to Blatche seemed to be a reasonable bargain for Washington.
He deserved the money, for a little while anyway.
Then, with Washington struggling in the win column, attitude issues began to surface. Blatche was suspended the day after Christmas for an incident in a night club that also involved teammate JaVale McGee.
Attitude issues continued for Blatche, as he often appeared disrespectful of his coaches and had some beef with then-head coach Flip Saunders.
Blatche was waived on July 18, 2012.
Date: Nov. 24, 2008
Having led Washington’s playoff runs from 2005-2008 couldn't save head coach Eddie Jordan from being fired after his team's abysmal 1-10 start to begin the 2008-09 season.
The knee-jerk reaction that occurred after the poor start was one of the major factors in Washington's collapse, one that has hardened into continued years of futility and features a revolving door at head coach.
Jordan designed an offense that not only allowed Arenas to be a star. It also was dynamic enough to allow Jamison and players like Caron Butler to realize their potential as explosive offensive players.
Jordan was the right coach for that Wizards team, and though replacements like Flip Saunders and current coach Randy Wittman have put forth the best effort possible, neither has fared as well as Jordan did during his six-year tenure with the team.
Barbosa was not in good shape when the Wizards acquired him.
Date: Feb. 21, 2013
No one said it better than NBC Sports' D.J. Foster when he declared “anytime you can trade a guy with one functioning ACL for a guy with two, you have to do it.”
When the Wizards sent Jordan Crawford, the man with two strong knees at the time,to Boston February 2013 for Jason Collins and an injured Leandro Barbosa, the move drew some well-deserved criticism.
Sports Illustrated's Ben Golliver called the Wizards motives, "difficult to determine: The Wizards must have concluded that Crawford wasn’t worth the headache and/or worth playing in the final year of his rookie contract."
Crawford must have been a big headache.
Date: Dec. 19, 2010
For the record, getting Rashard Lewis for Gilbert Arenas was about as good as the Wizards were going to get as a return.
The contract details that will soon be disclosed were so lofty and unattractive given Arenas' worsening injury history, most NBA teams looking to compete would not touch the former star with a 10-foot pole.
Luckily, most NBA minds thought the same about Rashard Lewis, who at the time of the deal had two-and-a-half years left on a six-year, $118 million dollar deal.
As for his play once he arrived in Washington, Lewis was hardly inspiring. In 60 games with the team, he flirted with the lowest three-point totals of his career (.347 and .239, respectively). This was surprising, considering he spent each of his two years playing along side the pass-happy John Wall.
Ultimately, Lewis' spot on this list is entirely due to the hole in which Arenas left the franchise.
Unfortunately for Grunfeld, Lewis failed to fill this hole.
Date: July 13, 2008
The Wizards re-signed Gilbert Arenas to a six-year, $111 million contract in 2008, a handsome reward for being the team’s primary option during their playoff years.
Unfortunately for Arenas and the Wiz, a horde of issues with both knees led both player and team on a downward spiral.
Knee issues followed Arenas into the season, as he missed five months of action, several more than fans could have ever hoped for. Arenas returned in March of 2009, but his undedicated approach to handling his knee injuries had soured the star player’s reputation in the eyes of many fans.
With his trade options limited—no other team wanting to absorb such a large contract—Arenas became dead weight for the franchise.
It was not until a New Year’s Day, 2010 locker room-gun incident involving Arenas that things appeared to improve for the Wizards and Arenas’ whopping contract. While the incident remains off-putting, it allowed the Wizards the opportunity to void Gilbert's large contract.
Despite this chance to bail on Arenas, the Wizards elected not to void Arenas' contract as a way of displaying what The Washington Post suggested was the team's loyalty to its star.
While it appeared that the gun incident offered Washington a get-out-of-jail-free card, the organization decided against the move...and paid the price because of it.
What the Wiz could have had with the No. 5 overall pick in 2009
Date: June 24, 2009
The pick was at No. 5 overall, despite originally belonging to the league’s second-worst record.
The Wizards bailed on a lottery-pick in a highly talented draft class. Blake Griffin was a shoe-in for the No. 1 overall selection, but any arrangement of Hasheem Thabeet, Tyreke Evans, James Harden, and Rubio could have occurred after that.
In return, the Wizards received Mike Miller and Randy Foye. While both contributed in their first season in D.C., both would not stay longer than one year.
What the Wizards gained in Miller and Foye—three-point shooting and secondary ball-handling—could not have been more available in the draft.
Getting the opportunity to select John Wall No. 1 overall the following year eased some of the pain of clearly losing Rubio. This trade serves as a model example of Grunfeld’s willingness to forgo the team’s future success in favor of current stars.
The strategy worked in initially getting Jamison, Arenas and others—and its been good to the Wizards for the most part.
But even the stubborn president of basketball operations knows, it’s time to reload if he wants a long string of playoff success.