That's one way of looking at it. Or, he signed for more guaranteed money. Here's one back-of-the-envelope analysis of the risk angle. Twins guarantee 3 years for a total of $42M. After that, various things can happen in Year 4, one of which is the triggering of the vesting option. By comparison, the Brewers guarantee $50M for 4 years. So, from a monetary standpoint, it comes down to what the odds are that he'll get more than $8M in that fourth year if he takes the Twins offer. If for simplicity's sake you assume only two possible outcomes, either the Twins $14M vesting option happens, or else it's $0, then if he thinks it's 50/50, he's money ahead taking the sure $8M. Do you gamble $8M in hopes of winning $6M? You need good odds for that. Of course other possibilities exist for that fourth year, and you also have to factor in the question of Year 5, which under the Twins plan is free agency and with the Brewers is a vesting option for $13M. So I'm sure his agent went through various scenarios, and gave the spreadsheet program a good workout. If he's completely not confident in his own health for the long-term, he'll take the greatest guarantee, period. But even with good confidence, the potential payoff has to be pretty high in order to make a gamble worthwhile.