Chicago Cubs: The plan worked, but then stalled
From the start, Theo Epstein’s plan was to buy pitching and draft elite hitters. Albert Almora, Kris Bryant, Kyle Schwarber, Ian Happ, Nico Hoerner. Every first-round hitter Epstein has drafted (other than 2020 Ed Howard) has already made it to the bigs and had an impact (even if some have stalled, been inconsistent, or fallen off since). In fact, every single one of them had immediate impacts upon hitting the big stage. The first three were key cogs in the ’16 World Series. Happ and Hoerner may be cornerstones for the franchise for the next decade.
Part A of the plan went pretty much to plan. Part B was to buy or acquire pitching. Kyle Hendricks, Jake Arrieta, Pedro Strop, Mike Montgomery, Carl Edwards Jr., Dan Haren, Aroldis Chapman, Alec Mills, Jose Quintana, and Wade Davis were all traded for. Check. Jon Lester, John Lackey, Yu Darvish – all signed to deals, with Lester’s and Darvish’s doozies.
Seems like everything went to plan. And, to be fair, it did in that the Cubs won a World Series directly because of that plan. The signing of Lester and trade for Chapman accentuate exactly what it takes to win sometimes – overpaying on the back end to get the elite front end of a top line starter and giving up a stud prospect in Gleyber Torres to get the guy who carried the pen into the World Series.
The problem was that during most of that time, not one Epstein-drafted pitcher made it to the bigs. Now, international signees Adbert Alzolay and Brailyn Marquez have finally made it and could be rotation pieces in the future, but the Cubs just haven’t been able to supplement the rotation with homegrown talent in the last couple years as the finances have dried up a bit. So, while the philosophy worked to get one trophy, it would seem it hindered adding multiple trophies.