The Celtics knew the guy that they liked. It was Tatum. They talked about potentially taking him at 1. It wasn’t a gamble to get an extra first round pick to get your guy two picks later.
And the Kyrie trade? Really? They gave up damaged goods and mediocre role players for one of the best PGs in the league (and at that point people were higher on Kyrie than they are now). Any GM would give up 1 pick that could possibly be a top 3 pick for a player like Irving with 3 years left on his contract (especially when he says he will resign). They really screwed up not being able to keep Kyrie.