How? Whether the team that signed him to that deal paid that money sooner or later, they were going to pay it anyway. Toss the money in with the deal if that's what's keeping the deal from happening. Let's just keep throwing money at the player. Assuming this was a normal Cubs signing of the past handful of years, the player was already 30+ and declining in value. In a 2/7.5 contract, I'd rather pay 4.8 and 2.7 assuming the player in his prime now will perform at a higher level then next year when older. Additionally, in year 2, a potential trade partner could view the lower value as an acceptable level of compensation instead of requiring money with the deal. It's not about the total value you're spending on the player, it's aligning pay and performance. If you want to backload a 5 year deal for a 26 year old, that'd align with expected performance curves. But if you pay the guy 2.7 and 4.8 instead, that gives you flexibility. You might only have to throw 1 million into the trade to make it work. Even if you have to throw in the full 2.1 to make it work, you're not in any worse shape than if you had paid the 4.8 to the player to begin with.