I wonder if the prerequisites for applying for police chief in the counties state that you must be anti-2a.
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One of the issues there is that not every state uses their LE agencies the same. In some states, the cities have not incorporated the entire county, so while the city cops have jurisdiction inside city limits, the Sheriff has jurisdiction within the unincorporated county lands.
Also, most states have a state highway patrol. They have statewide jurisdiction, but will normally only be called in for local crimes if there's a conflict of jurisdictions or a cross-over to more than one. Otherwise, they stick to the state and federal highways.
Here, each island is part of a county, and the cops are supposed to enforce laws in the entire county. Sheriff is organizationally part of the department of safety, and they are tasked with security at airports, courthouses, etc. You won't see a Sheriff's Deputy being asked to respond to a 911 call ordinarily.
Having said that, Cops are usually pro-gun control because it can make their own jobs safer. While the laws do nothing to stop criminals, the law-abiding man or woman interacting with a Cop will be unlikely to have a firearm in their car or holstered.
I'm not as sure the Chief is anti-2A, or if his on-the-job safety is being placed above the Constitutional rights of the people he serves.
Conflict of interest more than a political or personal position against the 2A.