Sure, but it's not true that you should never volunteer to pay out more money at the start than at the end. You can get the overall value of the contract lower, and can fit it into your budget better when appropriate. There are a variety of factors to take into account, including expected tax rates. If 2 teams are offering the same guy 2/50, you can front load it to make your offer more attractive. In general, yes, it's cheaper to backload. But paying more early on can make sense and you should not completely rule it out. The budget isn't a factor, as I said you budget however you see fit. Pay the player 20M, but put that other 10M aside to be paid out in '18. If you're offering 2/50 and you're front loading it then your offer is more than the other team's 2/50. Expected tax rates is something I'd never considered, but I can't imagine a player taking less money because you frontload the contract. Especially on something as tenuous as an expected increase in their tax rate.