Front loading a deal is not necessarily always a poor decision. A lot comes down to the details. The big thing for the player is the actual value of the contract. What I mean by that is the details of the payout. A three year deal, $60M contract paid out in equal terms ($20M annually) is worth more money than a contract that pays $10M, $20M, $30M. That's because the player gets $10M two years earlier - and thus now has money to invest and make more money. Thus, the three year, $60M contract, paid out equally over three years, might be more equal if the payout was something like $10M, $20M, $33M. That's a 3-year, $63M deal, technically worth 'more' money than the other deal - but in reality, the same. BTW, I'm just guessing at what the actual equal value is by tacking on the extra $3M to the last year. I really don't know how that kind of stuff is calculated. That is one reason why clubs like contracts to be backloaded. The more money pushed into the future, the more money they have at this time to use on their product (or to invest or whatever). All that said, it doesn't mean you can't front load a contract for good reason. Let's take Arrietta as an example. The team could offer him the following (again, just an example): Option 1: 4-years, $100M, with annual payouts of $25M. Simple enough. Option 2: 4-year, $95M, with annual payouts of $30M, $25M, $20M and $20M. Option two has less total 'add 'em' value - but because he's getting more money up front, it would allow him to generate more revenue earlier (again, I don't know which would be more valuable - the numbers are just there to get the point across). The value to the player aside, the front loaded option might appeal to the Brewers due to the circumstances of the organization's financials. They may prefer spending more money now on a guy like Arrieta because they know that costs for other players will go up. Essentially, it comes down to a 'we have the salary room now, so let's spend it now, and not overburden our salary structure down the road'.