I think Reiss is very much onto something with the extra conditional #1 pick(s). If the core issue here is information and valuation asymmetry--the Pats believe, based on their superior information and assumptions, that Jimmy G is way better and worth way more than the specific market buyers are willing to pay (including the insurance value to TB12 in 2017, there is a way to solve that problem and bridge the gap. It just takes a little more creativity and complexity in the deal making.
It's done all the time in business transactions like M&A. Seller thinks business is worth a lot more than the buyer is willing to pay. They agree to exchange $X now plus a contingent payment based on how the business performs under new owner.
Same concept/solution possible here. Exchange something now like a #1 or #2 plus other goodies, and based on a mutually agreed/acceptable definition of JG's "performance" for the new team over time, much more value is exchanged, such as future #1s+. Said differently, if buyer KNEW they could get 3-5 years of really good franchise level QB play from JG starting this next season, they'd willingly give up a lot more.
I see how that works in the context of the NFL from the Buyer's perspective, but I'm not sure what the Seller gets out of it.
Players' contracts are sometimes structured around incentives like Games Started, making the Pro-Bowl, being named All-Pro, etc., but it's hard to imagine how such a Trade could be structured where the benefit wouldn't be 90% on the side of the Buyer.
If I'm the Seller, I'm thinking that there are too many variables outside of my control that could come into play in the performance of a QB that I might be trading...strength of schedule, Offensive Line performance, Running Back and Receiver performance, injuries to one or more players, etc. So, I'd want full value up front. Period.
Anything else would just be sweetening the deal because I really don't want to sell but I might let him go if you're willing to pay more than he's worth (Dan Snyder and Woody Johnson come to mind).
It might work for a Team that's trying to unload a Cap-heavy player, but that's not the case with Garoppolo.
In a business transaction a Seller doesn't (rationally) sell a business for less than the Seller determines to be its economic value. It's possible to structure an Earn-out whereby the Seller shares in an identifiable upside, but an earn-out is usually put in place when the Buyer knows that the future success of the business depends on the continued involvement of the Seller.
If a Buyer isn't willing to pay what the Seller thinks the business is worth, a rational Seller seeks another Buyer. But, as with the Trade, a Seller who really doesn't want to sell might let the business go if someone is willing to pay more than it's worth.
I think both the NFL and the Business example would fall under the general heading of The Greater Fool theory.
Of course, in the case of a so-called Merger of Equals, both sides are incented to make the deal work, but an NFL trade bears no resemblance to a Merger of Equals.