1. Jake Arrieta. You could reasonably put the first three pitchers on this list in any order. All three were born within a six-month span in 1986. Currently, Arrieta stands as our “top gun.” Since joining the Cubs in a legendary 2013 trade, the righty boasts a 2.52 ERA and 8.9 K/9 in 634 2/3 regular season innings. He peaked with the NL Cy Young Award in 2015, and also finished ninth in 2014 and ’16. Arrieta will pitch the 2018 season at age 32, which makes a six-year deal a long shot. Zack Greinke is an exception, though his contract is probably one most front offices do not want to emulate. As a player known to be in top physical condition, Arrieta at least has a case for six years (but almost certainly not seven). He’s been DL-free since a stint in early 2014 and has a relatively low pitching odometer, as agent Scott Boras likes to say. Before Arrieta can make the six-year argument, however, he must shake off a decidedly mediocre finish to his 2016 season, as he posted a 4.05 ERA and 3.75 BB/9 over his final 20 regular season starts. Aside from the term, there’s also the question of average annual value. That could push into the low-$30MM range, as achieved by David Price, Max Scherzer, and Greinke.
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