Originally posted by Draftology:
Players want their guarantees spread throughout the contract to help ensure they capture the non-guaranteed portion.
This is true, but the more important piece of contracts is how the non-guaranteed amounts are structured. Players would prefer the non-guaranteed amounts to be as small as possible and as short term as possible to avoid the risk that they underperform their salary which is the basis for getting cut (once you're worth less than the amount the team saves by cutting you, you're at risk of being cut). And there's the time value of money argument where players are better off getting paid earlier (doesn't apply to signing bonuses, because the player receives those right away even though the cap hit is spread out).
Example:
A player is signed through 2018 with a non-guaranteed salary of $5 million and a prorated bonus of $10 million in 2018. If the player is worth less than $5 million, the team cuts him.
The same player is signed through 2018 with a non-guaranteed salary of $5 million and no bonus. If the player is worth less than $5 million, the team cuts him.
The $10 million of prorated bonus in this example is a sunk cost. The team will owe that in 2018 regardless of whether or not they cut the player. The guarantee doesn't impact the decision to cut a player unless we're talking about cutting a player who has years of bonuses remaining on his contract and the team considering cutting him isn't willing to take the cap hit for those future bonuses next season (you're required to when you cut a player).
It's in the best interest of the team and player to spread out signing bonuses over the length of a contract or 5 years (the league allows you to spread it out over a max of 5 years or the length of the contract, whichever is smaller). As a player, this provides the team incentive to keep you early on so they don't take the cap hit for the remaining bonus next season (there's a small chance that a team may keep you even if you're underperforming your salary to avoid taking the cap hit from future bonuses next season). As a team, this gives you more flexibility in the short run while not impacting your future cap, because you roll over any saved cap room. And if you do decide to cut a player, you're still in the same cap space situation you would have been had you taken the cap hit from the bonus earlier.