The question for Henry is “at which point do LT penalties hurt?” Last year, they were escalated, but the base was 20%. This year, the base is 30%. Next year, it’s 50%. I’d anticipate a title more than makes up for the financial loss, but at what point does he decide to re-set. These long term deals do help short term, but you could be locked into LT hell past the primes of the players you’ve got under contract. That was where the Yanks were after 2012. We were above average, being over .500 every year and making the playoffs once in a 4 year stretch, yet never being good enough to really contend. I know no team wants that, but if the Sox are WS contenders for a couple years, then that makes the decline phase worth it. What it comes down to is the longer Henry tries to prop this up beyond this season, the longer the decline phase will be.