Your comparable shows how much money is a stake. $23 million vs 10. I guess a lot comes down to what kind of insurance is available and how much it costs. Maybe anyone can get insurance against future earnings but there is probably a big difference in cost for a person with a contract. Maybe I am not understanding what you are trying to say. I posed the question as to what is better for the player. Injury is the thing. Cousins really had no choice because the Redskins did not really want him long term. It worked out for him but other positions are probably more vulnerable to injury these days. With your example, I would think Henry would be better off with a contract since he is at the higher end of the pay scale. Of course that could change. But it seems a big gamble.
My quibble was with the words "intimidated" and "gamble".
Obviously players want the security of more guaranteed money over multiple years. That requires no discussion. However, whether it's a franchise tag or 5th. year option, the player is under contract for the coming season and does not have much of a choice in the matter if the team is not willing to pay up.
The player's only option other than playing on that contract if the team balks at his demands is to ask for a trade and/or, hold out, get suspended, not get paid at all, and go into the red if the team demands collection of the no-show fines. It's rare for a player to pull a Le'Veon Bell and sit out an entire season for those obvious reasons along with the less obvious reason that hanging his team out to dry is a black mark on the resume as a consequence. Bell ended up signing with the Jets for less than what the Steelers offered as a result of that black mark, while foregoing a year of pay. I don't know if the Steelers collected those fines.
So, unless the player wants to make the injudicous move of a hold out there isn't any "gamble" on the player's part. There's only a negotiation. If the player knows he'll be playing one way or another, I doubt "intimidation" is the overriding emotion. Being p*ssed off is what it's about and the team risk is he starts stirring up sh*t in the locker room as was reported with Sitton when he didn't get an extension.
Now, is it possible a player on a franchise tag or 5th. year option will make business decisions on the field to the detriment of performance? I suppose that's possible, but you would expect the player to fight that inclination since it is cutting off his nose to spite his face, diminishing his value going into the next negotiation. He's playing in a contract year.