Considering how devoid of early picks Windsor's draft cupboard was Rychel has done an excellent job of bringing the pick situation back to balance, even adding a couple of extra for the 2021 draft and beyond.
As for the next 3 drafts I would consider the picks added to be only fair at best. Considering Rychel moved 4 of the biggest pieces available in the next 3 drafts he only added a combination of 5 2nd and 3rd rounders but one of those had to be given up to meet the conditions of the Laishram deal.
Adding a 2000 born and 2 2001 born players helps adding youth to the line up this year but looking beyond the deals and seeing the immediate future of Windsor's draft board shows there is still a lot of work to be done.
Some will say those picks or extra picks if Windsor chooses to add them can be acquired before the draft (referring to 2018 draft) while true each such deal to add extra picks or fill in remaining holes will create at least 2 more holes down the road.
If DiPietro, or others are moved next year that should help fill in some of the missing picks in the 2019 and 2020 drafts as well as add a couple of extras down the road for future deals.
While an overall good job at adding youth/restocking distant picks not exactly a great job with the immediate future/next 3 drafts only slightly improved.
Updated Picks
2018 - 1, Sag 2, Sag 3, 6, 7, Sar 8, 10, 11, 12, 13, Kit 13, Ott 14, Ott 15
2019 - 1, King 2, 4, Kit 5, 6, 8, 9, 10, 13, 14
2020 - 1, King 3, 4, Osh 4, Kit 4, 5, 7, 8, 9, 10, 11, 12, 13, Ott 14, 15
2021 - 1, Sud 2, 3•, 4, 6, 7, 8, 9, 10, 11, 12, 13, 14, Bar 15
2022 - 1, Bar 2, King 2, 3•, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15
2023 - 1, Kit 2, 3,King 3 (cond), Kit 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15
Kingston 3rd conditional on Vilardi playing 1 playoff game.
• Windsor 3rds in 2021 and 2022 conditional on Graham Knott playing an OA year and/or Trent Frederics reporting. Appears conditions won't be met and Windsor will retain both picks so I have added them back to Windsor's pick list here.
2024 - 1, Kit 2, Bar 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15
2025 - 1, King 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15
Windsor 2nd in 2025 was a conditional pick to Kitchener that was to be upgraded when Windsor acquired a higher pick. It's been reported here and elsewhere that the conditions were removed which I assume to mean Kitchener keeps the 2025 pick instead of an upgraded pick. If this is incorrect someone please correct.
2026 - 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 15, 15
2027 - 1, 2, King 2 (cond), 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15
2028 - 1, 2, King 2 (cond), 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15
Kingston 2nds in 2027 and 2028 conditional on Vilardi returning in 2018/19 season. Vilardi expected to make LA and not return so Windsor likely doesn't see these picks.
There are other conditional picks involving Windsor in mid/later rounds. Only 2nd/3rd round conditionals accounted for.