Yeah except the variance in the likelihood becomes increasingly small between picks as you get out of the top 10-15 in the draft. Obviously if Toronto tanks it this season and next (the pick is conditional), and somehow it ends up being a pick in the top 15 for Carolina, this looks a lot worse for the Leafs. However, I think Dubas was pretty safe gambling that this would be a pick closer to the 24-31 range (as it has been the past two seasons).
This off-season, Dubas successfully offloaded Marleau ($6.25M), Zaitsev ($4.5M), and Brown ($2.1M), and in total, traded away three 2020 draft picks (1st, 3rd, 7th) and acquired four (3rd, 4th, 6th, 6th). In terms of expected pick value, he traded away approximately 501, and gained approximately 420 (based on last year's standings)...the disparity in value of those picks, 81, is equivalent to about the 146th overall pick in the draft.
So, essentially this off-season, Dubas did the following:
In - Tyson Barrie ($2.75M), Alex Kerfoot ($3.5M), Cody Ceci ($4.5M), Aaron Luchuk (ECHL), Ben Harpur (AHL), David Clarkson (LTIR), Jordan Schmaltz (AHL)
Out - Nazem Kadri ($4.5M), Calle Rosen (AHL), Patrick Marleau ($6.25M), Connor Brown ($2.1M), Nikita Zaitsev ($4.5M), Michael Carcone (AHL), Garrett Sparks (AHL), Andreas Borgman (AHL), 146th overall pick.
So in essence, you lose two useful players (Kadri & Brown), and replace them with two useful players (Barrie & Kerfoot), while offloading two negative players (Marleau & Zaitsev), and replacing them with only one negative player (Ceci)...otherwise its just minor leaguers getting moved around. In total, this saved Toronto $6.6M in cap space, all for the price of a 146th overall pick.
That $6.6M is basically what allowed us to bring Johnsson & Kapanen back. So as important as draft picks, and that lottery ticket for new ELCs are...I don't think you can argue that Johnsson + Kapanen < 146th overall pick.