With almost the entire roster from the 2008 Olympic Team now playing in either Miami, New York and Los Angeles, the superstar carousel begun by the creation of the Big Three in Boston is finally starting to slow down. Now that most of the stars of the draft classes of 2003-2007 have found a long-term home, with the notable exception of Dwight Howard, speculation will inevitably turn to the 2008 and 2009 draft classes.

That’s why Kevin Love’s recent comments about his frustration with the Minnesota Timberwolves are so interesting. While he’s still locked into a long-term deal, the seeds of his eventual departure have clearly been planted. And if Love follows the career path of the last All-NBA power forward named Kevin in the Twin Cities, the team’s mistakes in the last four drafts will be the biggest reason why.

Minnesota isn’t Miami or Brooklyn; they can’t depend on attracting star-level talent in free agency. Brandon Roy isn’t exactly the player he was in 2009, and even if they grab Nic Batum in restricted free agency, they’ll be overpaying for a perimeter stopper who will only be marginally effective without an elite rim protector behind him.

The draft is the only place where the Timberwolves can acquire the high-level players who could convince Love to stay long-term, and, besides Ricky Rubio, they have failed miserably in that department under David Kahn. Minnesota had multiple chances to assemble an “Oklahoma City North” team around Rubio and Love, but now that Love is headed into his fifth NBA season, their window to get another Top-5 pick is closed. 

In 2009, Kahn sold high on Randy Foye and Mike Miller to acquire a second lottery pick. With four first-round picks, he had a great chance to build a young core around Love, who had just finished his rookie season. 

After taking Rubio No. 5, he bewildered many by selecting another point guard at No. 6 in Jonny Flynn from Syracuse. However, given Rubio’s size and defensive versatility at 6’4, as well as the number of quality players at the position in the draft, taking a second point guard didn’t have to be a huge mistake.

The mistake came in taking Flynn ahead of Stephen Curry, Brandon Jennings, Jrue Holiday and Ty Lawson (who Minnesota traded to Denver for a future No. 1). Any of the four would have formed one of the NBA’s most exciting young backcourts with Rubio or been an excellent trade chip; Flynn was eventually given away to the Houston Rockets and may end up out of the league altogether next season.

There were certainly red flags about Flynn’s game coming out of college. He had an inconsistent outside shot (32% from deep as a sophomore) as well as a lack of size (6’0, 185) that would make it tough for him to be a factor defensively or finish in the lane at the next level. 

In 2010, Minnesota “earned” the No. 4 overall selection, and once again did shockingly little with it. The Timberwolves selected Wesley Johnson, a 22-year-old junior from Syracuse and an unskilled and not particularly athletic 6’7 combo forward. Even in college, Johnson wasn’t effective creating his own shot off the dribble and taking the ball to the rim; Jim Boeheim’s 2-3 zone, meanwhile, hid his lack of defensive ability. 

His best-case scenario was as a replacement-level small forward who could defend and shoot, a low ceiling for a No. 4 overall pick. Even worse, Kahn passed on Greg Monroe and DeMarcus Cousins, skilled 6’11+ big men who would have been an ideal offensive complement to Love’s three-point shooting ability. While either frontline would have had issues defensively, which is why I think LaMarcus Aldridge is a more valuable building block than Love, both would have been nearly unstoppable on the other end of the floor.

Kahn’s failure to recognize the importance of a quality center continued in 2011, when he passed up on Lithuanian big man Jonas Valanciunas to take Derrick Williams with the No. 2 overall pick. Williams, who doesn’t have a defensive position and can’t create his own shot, is already on the trading block. He still has the chance to be an excellent player next to Rubio and Love, but his skill-set isn’t nearly as valuable as a versatile 6’11 240 big man with a 7’6 wingspan who can defend multiple positions, rebound, block shots, finish at the rim and stretch the floor.

While 2008 second-round pick Nikola Pekovic has emerged as a valuable contributor at the center position, his lack of shot-blocking ability is a problem next to Love. More importantly, if Kahn thought he could find minutes at the crowded 3/4 positions on his team for Williams, he certainly had room for a three big rotation of Love, Pekovic and either Valanciunas, Monroe or Cousins.

In 2012, Kahn bowed out of the draft completely, dealing the No. 18 pick for Chase Budinger. Budinger, an athletic small forward who can shoot and run the floor, may give the Timberwolves the production they thought they would receive from Johnson, but he doesn’t have the upside of several of the players Minnesota could have been choosing from. 

Role-playing wings like Budinger are fairly replaceable: the Philadelphia 76ers recently acquired Dorrell Wright for a player to be named later. At No. 18, Minnesota could have taken Perry Jones, a versatile 6’11 forward who would have been great pick-and-roll partner for Rubio, or Terrence Jones, a combo forward with more upside than Williams.

While drafting young players will always be somewhat of an inexact science, Minnesota’s track record is particularly gruesome. And if they had Monroe, Holiday and Perry Jones on their roster, Love’s future in the Twin Cities would be a lot more promising.