This was me, 2.5 years ago:
So, let's be frank: barring injury or huge dropoffs in production, there is nearly zero chance that Love exercises that option (regardless of whether he wants to remain a Timberwolf, since he'd make more money by opting out and signing a new contract), so this was a three-year extension. It's truly hard to imagine how a management team could screw up while signing the team's best player, but somehow, Taylor and/or Kahn managed to do it.
Basically, Taylor tried to play hardball with Kevin Love and got swindled in a huge way. And all for "future flexibility". Wait, so you didn't want to lock up a franchise player so that you could later, maybe...lock up...a...different...franchise player? Yeah, Mr. Kahn (Taylor), there's a reason I keep this GIF handy for my Timberwolves posts, because this is your management philosophy in a ****ing nutshell:
This was Glen Taylor, yesterday:
Taylor said he underestimated Love's ability to develop a lethal offensive game. But the reason Taylor didn't push for the five-year max, he said, was heath concerns about Love.
"I think Kevin, his offensive skills got better than I think we estimated. The only thing that I still have a question mark about will be his health. I had that concern then, I still have that concern and I think Cleveland should have that concern, too," Taylor said. "If they sign him to a five-year contract like they're thinking about, I mean that's a big contract in a guy that's had sometimes where he's missed games."
For the record, the decision point Glen is talking about is the contract extension. He's saying that in late 2011, after Love had spent the entire season in 2010/11 averaging 20 & 15 with 59.3% true shooting (and going to the line about 10 times per 48), they didn't think Love had a "lethal offensive game", nor did they think he could develop one. The 2010/11 season, by the way, is still his best season offensively (although last year came very close). He didn't get better in the next few seasons; he just got more minutes and took more shots.
If you are ever wondering why free agents don't come to Minnesota, don't look to the weather. It gets cold in Chicago, New York, Boston, and...Cleveland. It's not the weather. It's the incompetent organization.