Why does David Kahn insist on torturing us so?  Why have we been taken for loop after loop as the Timberwolves franchise tries to shake the inescapable musk that comes with taking two point guards back-to-back in a draft crucial to its development?

Because everyone is human, life isn’t fair, bad things happen to good people, and nobody said it would be easy.  That, and the fact that David Kahn must either hate the fine few remaining card-carrying Timberwolves fans, or have a sick, sick sense of humor.

I was willing to play nice, all in the name of Jonny Flynn.  Flynn, like Rubio, is a rookie built on intrigue.  He’s an unknown, but one whose game is unmistakably ludic; watching Flynn is fun because it looks like he’s having fun.  Throw that kind of player into a situation with minimal pressure and expectation, and you’re on the brink of witnessing something special.  It won’t often translate to wins given how bare Minnesota’s armory is these days, but Flynn is exactly the kind of point guard that can energize a depressed fan-base.  And now, Flynn is a Minnesota Timberwolf.  His salary is set and his name is on the jersey, so let’s shuffle up and deal.

Oh, wait.  I forgot.  The man at the controls insists on pushing button after button, as long as each is cleverly labeled “ADD NEW POINT GUARD.”

In principle alone, I have absolutely no problem with adding legitimate talent for perfectly reasonable salaries.  That’s why I can’t be too upset about Minnesota’s 4-year, $16 million offer sheet to Ramon Sessions.  Applause for signing a real starting point guard for a sub-mid-level contract, especially after there was rumored interest from far more suitable destinations.

But once the applause dies down, let’s all take a deep breath and wonder exactly what the hell is going on here.

There’s a three-way duel for the point guard position in Minnesota.  At one vertex, you have Jonny Flynn, the good soldier.  He’s said all the right things since being selected by the Wolves in the draft, and has yet to voice any real displeasure with the team’s decision-making, despite being slapped at nearly every turn.  Kahn wasn’t confident enough in Flynn to go for a non-point guard in the draft to run alongside him…unless the plan really is to trade Rubio after driving Ricky’s stock to an absolute minimum and losing the higher ground at the negotiating table.  Then, just when the franchise should be shining Jonny’s shoes and giving him back massages, they go out and sign a capable, talented, young point guard to a 4-year deal.  We’re beyond the Wolves not showing confidence in Flynn.  Kahn is now going out of his way to ensure that Jonny knows just how little faith management has in him.

Then, supposing Milwaukee doesn’t match the offer sheet for Sessions, he’s certainly in the mix.  He would undoubtedly be Minnesota’s day one starter, but how high is Ramon Sessions’ ceiling?  Sessions has plenty of room for improvement, but his maximum potential seems a step down from the new kids on the block.  He also doesn’t have the star power of either a Flynn or a Rubio, a cruel fact that every small market team must face.  Even if Sessions is the wiser long-term commitment, would he bring in the sponsorships, ticket sales, and national media attention of either of the young studs?

And oh, let’s not forget our beloved Ricky.  He’ll be NBA-ready in two or three years, the perfect time to send the point guard rotation spiraling out of control.  Flynn will certainly have paid his dues by that point if he’s still with the Wolves, and to hand over the reins to Rubio would violate the smell test on more than a few levels.  But let’s keep things in the present, where the Wolves have seemingly squandered a pick on a point guard who may or may not be the star everyone (myself included) hopes him to be, and could conceivably bring the wolves some considerable misery along the way.  There is nothing wrong with drafting Ricky Rubio, but there could definitely be something wrong with drafting Rubio, drafting Jonny Flynn, and signing Ramon Sessions.  Someone will inevitably be left out in the cold or out of position, which hardly seems fair to the three involved.

There’s always the chance that Kahn flips Flynn, Sessions, or Rubio in a stroke of genius, netting the Wolves’ some much-needed wing help or the elusive beast known as a true center.  But as it stands now, the chips are certainly stacked against such an outcome.  In his short time with the Timberwolves, David Kahn has managed to take a series of moves that are stand-alone positives, and turn them into a logjam and a headache.  Though Kahn’s moves haven’t created a cap nightmare for the Wolves (Sessions’ proposed deal is more than reasonable, and Flynn and Rubio will be on the rookie scale), I wouldn’t ever call it wise to jab your point guards with sharp sticks.  A talented player can hold your team ransom in ways that even the salary cap can’t, and if Kahn ends up with tied hands and even less bargaining power at the trade table than he has currently, he’ll have no one to blame but himself.