He didn't learn from the Kevin Love situation because LeBron bailed him out. No more, no less. Just a rich guy who thinks he can motivate his players better than his coaches. Wiggins will sign the same contract next summer that Otto Porter did this year, and Taylor will get to decide if he wants to match it. It'll be a worse contract for the Wolves than they could get for Wiggins right now.
Why would 4 years 106 Million be worse than 5 years 148 Million? I think the wolves would much rather save 42 Million than just get 1 extra year from Wiggins. Plus Wiggins is going to sign that max 5 year extension anyway.
For starters, it will be for about $111 million, since the max salary will increase next year.
Secondly, it will contain a 15% trade kicker, which means the Wolves may wind up paying still a little more if they try to trade him. It also may have a weird salary date, which could also mean the Wolves pay more money if they trade him.
Thirdly, and most importantly, it will have a player option for year 4. So if Wiggins continues to get better, he'll get a new max deal at the 30% max-player threshold after 3 years, which will mean a higher salary than he'd otherwise make compared to years 4 and 5 of a max deal offered today. And if Wiggins is ticked off by Taylor, as Love was, he will signal that he won't re-sign at all after those three years are up.
If Taylor's basketball people think Wiggins isn't worth the max, then they shouldn't offer it to him. If they do, then they should. Taylor's role should be as a cheerleader urging Wiggins to sign it and become a franchise player, not as someone who's trying to play mind games.