19. Toronto Blue Jays

Few brain trusts face a more delicate challenge than Mark Shapiro and Ross Atkins in Toronto. On one hand, you’ve got current franchise player Josh Donaldson staring down the barrel of free agency at the end of the 2018 season. On the other, you’ve got future franchise player Vladimir Guerrero Jr. tearing up the minors and closing in on his major league debut.

It’s in the vast space between those two that the details get muddled. The Jays made the ALCS two years in a row, only to tumble to an 86-loss season in 2017. Fielding the oldest group of position players in the majors bodes ill for near-term improvement, even as young pups like Teoscar Hernandez and Anthony Alford see more playing time, and older hands like Jose Bautista likely take off. Do the Jays try to build on two straight years of leading the AL in attendance, seeking short-term solutions in the hopes of keeping the revenue gravy train rolling? Or do they acknowledge that signing Donaldson well into his 30s might be a bad idea, that the Yankees and Red Sox are better equipped to make playoff runs this year, and that the sooner they make aggressive moves and start something close to a rebuild, the sooner they can field a consistent contender? Tough call.