Almost all businesses operate on a budget, usually annual. Braun's salary in future seasons will be a part of that budget, unless it gets moved sooner as a "prepaid expense". If the Brewers pay it earlier then they would discount that for the time value of money - it wouldn't cost "millions more". Discounting $19M (2019 salary) for two years at 5% per year yields a net present value of ~$17,200,000, or a difference of $1.76M. If you were to offer to split that with Braun evenly it would cost $880K, and I'm sure Braun would jump at it. Discounting Braun's 2020 salary ($17M) by three years at 5%/year yields $14,685,000 net present value. I don't think the OP was intending to entirely pre-pay it, but to front-load some of it so the future salaries (that will count against future budgets) will be reduced, allowing for the addition of more players/salary expense in those future season's budgets. Most businesses set their budget based on how much they have to spend. If they take the same money they are saving now and invest it that money will grow so they can set a higher budget later. If they just give it to Braun now all the money that investment would have made is lost. Which is what the calculation he did allows for...part of it is inflation, part of it is opportunity cost. It would have to be a bigger number than 5%, but the calculation can be made.