Scharf's resignation isn't being questioned by many yet the same can't be said for Oberhelman.
The timing is also suspicious given the fact that the company just exited its longest streak of revenue declines since the 1980s.
Sutherland suggested that Oberhelman's resignation is a sign that he isn't optimistic that the business will significantly improve in the next two years. Naturally, this isn't encouraging for investors who are just getting used to the stock trading near its highest valuation relative to projected EBITDA since 2010.
Meanwhile, Wall Street analysts were modeling Caterpillar's revenue to continue falling in 2017 after dipping nearly 15 percent this year. That would imply the company is operating at its lowest revenue total since 2009, which also marks the year when Oberhelman became the CEO-elect.
"But steering the company toward a rebound will now be someone else's problem," Sutherland concluded.
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