So is Jeff Bennett removing the signs on his own misinterpretation of state Code(s) or is he being directed to do so? There is nothing in the Streets and Highways Code pertaining to “political” signage. Per state Business and Professions Code, the signs aren’t “political” since they’re not placed to influence votes for a scheduled election.

Business and Professions Code, Section 5405.3:
5405.3. Nothing in this chapter, including, but not limited to, Section 5405, shall prohibit the placing of temporary political signs, unless a federal agency determines that such placement would violate federal regulations. However, no such sign shall be placed within the right-of-way of any highway or within 660 feet of the edge of and visible from the right-of-way of a landscaped freeway.
A temporary political sign is a sign which:

(a) Encourages a particular vote in a scheduled election.

(b) Is placed not sooner than 90 days prior to the scheduled election and is removed within 10 days after that election.

(c) Is no larger than 32 square feet.

(d) Has had a statement of responsibility filed with the department certifying a person who will be responsible for removing the temporary political sign and who will reimburse the department for any cost incurred to remove it.

And there’s Caltrans’ maintenance policy governing outdoor advertising/signage:

9.00 Introduction
Outdoor Advertising, to control the placement and maintenance of outdoor advertising displays
that can be viewed from the State’s interstate and primary highway systems, is administered by
Headquarters Traffic Operation Division.

9.01 Removal of Illegal Advertising Displays within the Right of Way
Maintenance forces are authorized to remove and destroy any advertising display, placed within
the right of way without a Removal Authorization from the Headquarters Traffic Operation
Division. Advertising displays may be stored at the nearest maintenance yard for 30 days,
during which time the owner may claim the display.

9.02 Removal of Illegal Outdoor Advertising Displays on Private Property
The Outdoor Advertising Act empowers the Director to remove illegal displays from private
property. Maintenance forces are authorized to remove such displays upon request by the
Headquarters Traffic Operations Division. Outdoor Advertising removal requests are sent to
Region/District Divisions of Maintenance by memorandum requesting removal, a listing of
display(s) to be removed, the citation(s) and the Removal Authorization Form(s) (ODA-0015) to
be completed and returned to the District Division of Traffic Operations. If the removal crew
finds that the violation has been corrected, no further action will be taken. The Removal
Authorization Form must be returned to Headquarters Traffic Operations Division with a
notation that the violation has been corrected. If for some reason, the removal crew is unable to
remove a display, the reason should be noted on the Removal Authorization Form, which should
immediately be returned to the Headquarters Traffic Operations Division.

The Removal Authorization Form includes Cost of Removal. The cost of all field work involved
in the removal and destruction of illegal outdoor advertising displays from private property by
Maintenance forces shall be charged to Source 52465, Expenditure Authorization 952130,
Activity 040. This information should also be included on the Cost of Removal portion of the
removal Authorization so that Headquarters Traffic Operations Division can bill the violator for
removal of the display

Did the misinterpretation of sign removal regs come from the Director level?