It doesn't happen with any regularity. It's a rarity. I overspoke in a literal sense with "ever" but the fact remains: it isn't a viable method. You're welcome to show how many actually happen, I believe you've pointed out the only two in recent memory, but maybe there is this long list of them that shows it is viable. By all means. Considering the power players have in negotiating....if they wanted it....wouldn't it happen more often? They negotiate all sorts of comical, ridiculous, brazen things into contracts but front-loading is extremely rare. If it makes so much sense, why aren't some of the top-end FAs demanding it? Surely some team (like Seattle for Cano - someone always ponies up if you're talented enough, no matter how huge your demands) would give in. The simpler explanation isn't that all the teams have unified as one to deny this to players (when does that ever happen when it comes to these things?) but that the actual union is the one keeping it off the table? In fact, even A-rod, who you cited before - had in his contract that if any player was paid more than him the team could pay him 1M more and avoid the contract being voided. Ensuring his deal was backloaded or voided so he could re-negotiate. I don't deny it's speculative and all the articles I'm sure you googled thought (as you did) that it was a team driven phenomenon. Very few people seem to approach it from the opposite perspective. I'll simplify:front-loaded contracts ultimately hurt bargaining position as well. With free agency so important, that's clearly going to be a heavy pressure to give in to and the union (directly and indirectly) puts a lot of pressure on players to operate not only on their best interests or wishes, but for the betterment of others now and in the future. The teams don't typically care how much they operate in the best interest of each other. That makes the simpler explanation that the players are driving it. The contrary thing to believe would be your position. That every team in the league has joined together in stupidity, solidarity, or something to not front-load deals. Even though all of us could come up with situations in which it would be a brilliant move by teams to engage in. With so many savvy front office people, surely some of these situations would be more recognized and taken advantage of. But they don't. Not small markets, not big markets, not mid-markets. No one does it with any regularity. Or even with semi-randomness. It's rare. So what's simpler to explain? How a unionized force is acting in a way to increase their bargaining position or that 30 teams of very smart people are intentionally or unintentionally overlooking more ideal ways of offering contracts?