Been tweaking this idea for a while, so it might be a little in-depth, but I'll try to explain this as clearly as possible. Talking about who teams should have taken in the draft with hindsight is common, so I've been thinking whether there's a way to quantify this to some extent. Here's what I've come up with: 1) Build a roster using your team's first round picks (primarily, I'll clarify below) over a 15-year continuous period. 2) You may select a player within any of the 30 picks after yours (or 28 for 1999 & 2000, 27 for 1998, 26 for 1993-97, 24 for 1992, 22 for 1991, etc). 3) If you wish to select some players your team actually selected, you must include the original pick within this range (so, if the team had the 20th pick, you can only take players selected from 20th-49th). If you do not, you don't have to include the pick. 4) If your team has 2 picks in the same draft, you cannot select a player that your team selected in that draft with one of your picks (you do not get an extra slot for this player in your pick range). 5) You may use 2nd round picks to fill out your roster, but you must build your roster with 1st round picks first, and you can only take players who fit into your empty roster spots with these 2nd round picks. 6) You may only use 2nd round picks in drafts that your chosen team took 1 or 0 players in the 1st round. If your team took 2 or more players in the 1st round, you cannot use a 2nd round pick from that draft 7) If your team did have a 1st round pick in a draft you take a 2nd round pick from, that 2nd round pick must either a) be outside of the selection range of your 1st round pick (eg if your first round pick was 20th, the second round pick must be 50th/51st or later in the 2nd, assuming a 30-team draft) or b) be used to select a player outside the range of your first round pick (eg if your first round pick was 20th and the 2nd round was 47th, you cannot pick the players taken from 48th-50th/51st). I'm sure some teams will not be able to properly fill out rosters in certain ranges, but I think this should at least make them reasonably rare. I'll post an example team I've put together as a reply.