Toffoli was a month before the deadline, I'd say that is close enough.
1st, 4th, 5th for Toffoli.
Then a 3rd, 3rd, 7th for Jarnkrok that year.
Then a 5th for Carpenter that year.
So 2022 deadline he sent 1st, 3rd, 3rd, 4th, 5th, 5th, 7th, that is a full draft worth of picks...
He looks like he just makes deals earlier than the deadline, which is the trend now... but he still makes deals.
He just makes bad summer deals...
Monahan for a 1st
A 2nd for Bennett
Tkachuk for what are now cap dumps
1st+ for Hamonic
He has made some good trades too though, the Hamilton trade is probably good.