In 2015, Jake Gatewood was given an advanced assignment to Class-A Wisconsin Timber Rattlers, jumping from rookie Arizona, where he had spent his 2014 season. He struggled in Wisconsin, striking out over 30 percent of the time and posting a 74 wRC+ (100 is league average).
The young slugger was subsequently sent down to Helena, where he performed more to his strengths, though he still posted high K rates. At the start of the 2016 season, Gatewood was again sent to Class-A Wisconsin.
Unfortunately, the first round pick struggled again in his early showing, striking out over 30 percent of the time, and posting a .