Usually when a team has two top six picks, as the Wolves did in the 2009 NBA Draft, they find a way to get at least one star out of the selections.
Instead, the sixth pick from 2009, Jonny Flynn, will be on his way out before the season starts, and the fifth pick, Ricky Rubio, will finally be joining the team.
In 2011, Minnesota needs to find and at least one long-term starter in a weak draft class.
Let's take a look at the 10 best prospects they should keep an eye on with both of their First Round picks.
In the eyes of most teams in the NBA, Kyrie Irving is the best player available in the 2011 NBA Draft.
So if he falls to the Minnesota Timberwolves at number two, they need to select him.
Now, if David Kahn truly believes in Ricky Rubio, he can move Irving on draft night and get some nice pieces in return. They could swap picks while adding a veteran or even trade Irving's rights for a solid veteran directly.
The Timberwolves know they cannot be as young as they were last season. From top to bottom, the roster was filled with youth. So, if Kyrie Irving is available, they should select him then try to get older by trading him.
Jonas Valanciunas would make for an interesting fit with the Minnesota Timberwolves organization.
David Kahn was right: Darko Milicic is better than we all thought he was going to be. Still, he was wildly inconsistent and probably not worth the money he was given.
Center is still a need for the Timberwolves.
If they trade down to the 6-8 range to add a veteran, Valanciunas needs to be looked at.
He is one of the best European players in the Draft, and some scouts think he will turn out to be the player from overseas that sticks around the longest in this league.
Even though he is not an option at number two, Minnesota needs to monitor the status of Valanciunas on draft night.
Kenneth Faried is a high-energy guy, and for a team that is somewhat led by the quirky Michael Beasley, accumulating high-energy players is never a bad idea.
For now, Kevin Love is the bright spot of this franchise at the power forward position.
Eventually, the team is going to have to decide how all of these big, young bodies will work together.
Anthony Randolph is not a good role player off the bench. He needs big minutes to productively contribute.
Anthony Tolliver might be worth a few minutes off the bench but doesn't seem like a great chemistry guy.
Tolliver could be called a poor man's Faried. The only differences are that Faried will probably be a better rebounder and finisher around the rim, yet Tolliver can shoot from outside from time-to-time.
If Faried is available, the Timberwolves should consider him with the 20th pick.
If Malcolm Lee were drafted by the Minnesota Timberwolves, he would instantly turn into the best perimeter defender on the team. That's how good he is, or maybe how bad Minnesota's defense has been.
Wesley Johnson showed some flashes of great on-ball defense last season but is probably more suited for the small forward position down the line. He is not agile enough to cover two-guards for 48 minutes.
Lee is one of the best defenders in the Draft.
With the 20th pick, it would be a significant reach to take him. However, they could do much worse with this selection if other shooting guards like Marshon Brooks and Klay Thompson are off the board.
The Timberwolves traded down and ended up with Lazar Hayward in the 2010 NBA Draft.
A similar situation could yield Lee, and Minnesota would instantly add a defender to the roster.
Tyler Honeycutt, despite playing a position already filled by Michael Beasley, could be a viable role player for Minnesota.
Honeycutt was a big-time recruit for UCLA and progressed throughout the season into one of their best all-around players.
He is a very good defender and can score at will at times.
Martell Webster is a decent option off the bench for the Timberwolves.
Honeycutt could be a lot better.
So they should consider him when the 20th pick rolls around.
Bismack Biyombo is an interesting prospect in this year's NBA Draft.
He was rumored to be a top five pick about a month ago.
Now, he is slowly dropping to the end of, or possibly out of, the lottery.
After the Draft Lottery results were revealed, some Minnesota fans believed that David Kahn would panic with the second pick and select Biyombo.
Now, the raw talent out of Congo may be available at number 20.
If he is, they should take a hard look at him because of his defensive prowess.
The Timberwolves struggle to protect the rim, and Biyombo could provide relief for this problem.
The Minnesota Timberwolves have selected a number of international prospects under David Kahn's direction.
Donatas Motiejunas may be a selection that fans can actually get behind.
He is a supreme talent that has seen his stock slowly drop to the middle of the first round for unknown reasons.
Motiejunas has been pretty inconsistent in workouts, but he has all the talent to turn into something special.
If Minnesota tries to knock it out of the park with the 20th selection, Motiejunas is the man to take.
Derrick Williams is likely to be selected second overall in the upcoming 2011 NBA Draft.
If the Timberwolves are still stuck in the second spot when Draft night rolls around, his chances of going number two decline a little bit.
Still, it is very likely that they would select him.
The Timberwolves should be listening to offers for every player on their current roster. Not a single player should be considered untouchable, including Kevin Love.
If Williams turns out to be much better than Michael Beasley, passing on him could be disastrous.
Thus, with the second pick, the Timberwolves need add the most talented player available, and that is Williams.
For some reason, yet another great scorer is being overlooked in the NBA Draft.
In the 2011 episode, it is Marshon Brooks, a stat-sheet stuffer coming out of the best collegiate basketball conference in the country.
Brooks could end up being the best pure scorer that comes out of this Draft.
Not only that, but he might end up being one of the few players not selected in the lottery that turns into a legitimate starter in the NBA.
The Minnesota Timberwolves would love to find a starter with their 20th pick.
If Brooks is available, to me, it is a no-brainer. Brooks should be selected.
With the second pick in a "two-player" draft, most teams will take one of the vaunted two players.
Still, the Timberwolves will have to consider other options with the number two pick.
One of these options is Enes Kanter.
If anyone were to shake up the 2011 NBA Draft, expect it to be David Kahn.
The selection of Kanter at number two would definitely change the course of the entire Draft.
Now, the best route for Minnesota would be to pursue a trade to move down and still select Kanter, if he is indeed their prized prospect.
Enes Kanter is the one top-five player in this draft that directly fulfills a need for the Timberwolves.
He will be on their radar throughout the next nine days leading up to the Draft, as he should be.
Timberwolves fans hope that if they do end up with him, it is not via the second selection.
That is a waste of an asset, and even Kahn rarely does that.