Would you accept this NFL draft-pick trade?

Theoretically, yes, on both counts. But I think that in the NFL, in the vast majority of cases, those concerns are unlikely to matter enough to move the needle. It’s not like the NBA where one star player typically turns around a whole franchise; unless you’re drafting a QB *and *he turns into one of the 5 or 6 best passers in the league, it’s rare that one guy is the difference between success and failure – and in any event it usually takes a few years for a player to round fully into form, and a 2015 1st Rounder may well be making more of an impact in 2016 than a 2014 2nd Rounder. A single player is also unlikely to make a difference financially: most teams sell out all their games anyway.

It will be more possible for a particular player to be an unusually good value for his draft slot (or an unusually good fit for his team), but I’m still confident that teams mostly overvalue who they perceive to be such a player and undervalue future draft picks.

That’s assuming you actually keep and use the 5 picks and keep the players. That’s not really the most likely scenario. These are cards in a deck that you can sell or trade at will.

Actually, the financial cost of 1st Round picks has been greatly reduced since the last CBA negotiation. 1st Rounders on their rookie contracts are now, on average, extraordinary bargains, providing far more expected value per dollar spent than anything you could hope to get on the open market in free agency. It’s nearly impossible for a team to have too many of them.

This is a no brainer if you have the job security the OP specified. Just look at how such these multiple draft pick trades turn out for players who are relatively known quantities. For example, the Hershel Walker trade was GREAT for Dallas, and the RG3 trade is turning out to be pretty poor for Washington.

More importantly, we can use history to judge this as well. Let’s look at how this would have played out in 2000. Let’s assume that the team trades for a top 5 pick. In 2000, they would have probably chosen on of the following players:

Courtney Brown (bust, 5 seasons played)
LaVar Arrington (3x pro-bowler, 7 seasons played)
Chris Samuels (6x pro-bowler, 10 seasons played)
Peter Warrick (bust, 6 seasons played)
Jamal Lewis (1x pro-bowler, MVP, SB Champion, 7 seasons played)

Now let’s look at the 1st round picks of the top two teams (Cleveland and Washington) from 2010-2014.

Washington’s Picks:

Trent Williams (2x pro-bowler)
Blaine Gabbert
Morris Claiborne
Desmond Trufant (7th ranked cornerback)
Gregory Robinson

Cleveland’s Picks:

Joe Haden (1x pro-bowler)
Julio Jones (1x pro-bowler)
Matt Kalil (1x pro-bowler)
Barkevious Mingo
Sammy Watkins

Yes, there are a LOT of variable here, but I would clearly take Washington or Cleveland’s picks than 1 person in the top list.

Incidentally, is there an *actual *limit on how far in the future NFL teams are permitted to trade?

If two teams made a deal - “My 3rd and 4th round picks in 2016 for your first-round picks in 2044, 2047 and 2049,” who could step in and void it?
You could argue “It a dumb trade,” but is it actually against the rules?

On the other hand, I think teams greatly overvalue first round picks compared to second round picks in the same draft. How much better are first rounders than second rounders, in terms of actual players drafted? Like, if we look at the past ten years, how much better is the group of first rounders compared to the second rounders?

This is a hypothetical question, not a request for someone to spend all that time compiling the player lists. While I assume the first rounders will be better, I don’t think they’ll be that much better that would justify how much more highly first round picks are valued.

First rounders are better - much better, really - but not enough better to justify their relative salaries, is the common belief. A hypothetical team full of first rounders would kill a hypothetical team full of second rounders, but if you had an arbitrary amount of money to spend you’d get more value spending it on second rounders.

The Ricky Williams trade was another notable example of a “I want what I want and I want it right now” trade.

I would take it given your conditions, but those conditions will never exist in real life so it’s pretty much academic.