The Timberwolves last went into the luxury tax in the 2019-20 season. Owner Glen Taylor approved then-President of Basketball Operations Gersson Rosas' request to move slightly into the tax to complete the trade for D'Angelo Russell.
Taylor ended up paying a few million to make that trade happen. That will be a pittance compared to what the NBA's final tax bill will once the Wolves are done in free agency this season.
The Wolves have made the decision organizationally to go for it. For this season and perhaps a few more, they will push all their chips into the center of the table, and maybe even go back to the cashier for more.