I voted yes... even though I would hate it, and it is objectively extremely risky.
My thinking is really changing personally on the importance of avoiding regrettable contracts. I think it may be that in some situations (Miggy in Detroit, as a random example) you have to swallow a contract that has some unambiguous bad years in it because that's the only way to add premium talent, which is generally a prerequisite to a championship caliber team. Yes, that deal hamstrung the Tigers, but, they could easily have won 2-3 titles with their core. I think it may be that in some other situations, you can accept the risk of bad years being part of a contract because either you have the payroll flexibility to absorb it (Arguably Giancarlo Stanton is a bit of this for New York right now) and/or expect the market to grow in such a way that the bad years are less awful when they arrive than they look to be now. In both scenarios, you may have a myriad number of outs that save your ass before the cows come home; maybe the player wants to be traded (Manny), maybe they age exceptionally well, etc.
Put differently: it is a bad value contract, but, I think it's become increasingly difficult to field championship teams with no bad contracts (or "future bad contracts") anywhere on there. The Astros, maybe, have sort of done it. The Braves model of extending guys early might be a way to work around it. But I think if you want to go to the championship, you often need a Chris Sale, Mookie Betts, or a Bryce Harper on the roster, looming bad years be damned. Especially if you're a team that has financial muscle as the Red Sox obviously do.