First of all neither 50K nor 150K will set me up for life. That's the biggest difference, either 100M or 300M is life changing money. If I sold that collectable for 100M and someone else flipped it for 300M in a few years I would be just fine. Going year to year is still a huge risk, he's only making near league minimum for 3 years, more than enough time to end up either with a career ending injury or somehow end up a bust. Also you don't know that the Braves had any interest in a deal without buying out some FA. That's the whole benefit for them. If Acuna wouldn't do it, they might have rather just gone year to year. Yes the odds of him getting a big deal are better at 28 than 31 but that difference doesn't prevent him from necessarily getting another great deal in his 30s like guys such as Goldschmidt, JD Martinez, Cain, etc, have all gotten. a) You missed the point. And you are in the minority if that doesn’t bother you...though you are lying even if you don’t realize it. Your nothing burger current state (compared to millions of dollars) makes you just happy at the thought of $100mil. However in reality once you get used to your new lifestyle the thought of $200mil and all you could do with it would make you very upset. Who is okay missing out on $200mil? b) I never said that, so that is good c) I never proposed that, so that is definitely good. I said buy out 2 years of FA, not the 4-6 he gave up. They would have 100% made a deal that bought out at least 2 years of FA and he is set for life. d) A new CBA could greatly suck money out of 30+ year olds. Players want money earlier, especially now that it isn’t flowing out to 30+ guys on the decline. I would not be confident get a big long payday at 30+ when that time comes. Too much uncertainty.