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Assume a private club located in a shopping plaza in Austin, Texas and they rent their space from the plaza's owner.

Also assume a member of the public, let's call him Larry, intends to stand outside, X feet from the club's doors, and hand fliers to their members as they leave.

What would be the required parameters, such as how many feet from the entrance could Larry lawfully stand? i.e. How much of the side walk is their premises?

Larry expects the club's staff to "sic" their security guards on him and try to "unlawfully(?)" and potentially forcefully remove him from the premises, but assuming he remains peaceful and does not intrude on their immediate entrance space, who in this situation would have the right to ask him to leave? The club, the owner of the shopping plaza or the police?

Chameleon
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The club renting space from the shopping center makes no difference; the difference is public vs. private land.

The legal controller of the land you are on - whether the shopping center, the club or private land around the shopping center - can ask you to leave at any time for any reason. There is no wiggle room. A controller is not necessarily the owner - a tenant is a controller as is an emergency service executing legitimate control.

The police are law enforcement; if you don't leave private land by request, their duty is to remove you at the request of the land owner. Private security also has the same function, though their jurisdiction is more limited off their property, as they are private hired by the shopping center or club.

Either would ask you to leave, and if you refuse, you could be arrested for trespassing.

If arrested, the local district or county attorney would have some discretion on prosecuting you for trespassing.

Dale M
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BlueDogRanch
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There were 2 cases which determined whether "pamphleteering" on walkways of privately-owned shopping malls was protected as free speech.

Every time I try to search for them, for some reason, I come up against this NY Times opinion piece from 1986 which explains it succinctly.

Hudgens v. National Labor Relations Board, 424 U.S. 507 (1976) determined that private shopping centers were not subject to Federal First Amendment constraints.

Pruneyard Shopping Ctr. v. Robins, 447 U.S. 74 (1980) determined that states enhancing freedom of speech rights by mandating access to walkways of privately-owned malls did not violate the mall owners' property rights under the Federal Constitution.

The result is that it is squarely up to the state whether this is legal or not. Some states have made it legal and some have not.

This memo, prepared for Connecticut General Assembly, reports that the 5 states which have mandated malls to allow pamphleteering on their walkways are "California, Colorado, Massachusetts, New Jersey, and Washington."

Texas is not one of those states.1 Which puts privately-owned walkways of malls in Texas on par with other privately-owned land. The owners have the same protections on that land as the stores have inside of their premises.

If a store owner can kick you out, then the mall owners can use the same means (whatever they maybe legally) to kick you out of the mall if you do not leave when asked.

1 The CGA report is from 2004. I have not been able to find if any other states have introduced similar enhancements to free speech since then. So the safe assumption is that none have (and, more specifically, Texas hasn't).

grovkin
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Trespass is a civil matter and a landowner, a lawful occupant (e.g. a tenant) or their agent (e.g. a security guard) may use reasonable force to remove a trespasser from their property. In this example, and assuming the sidewalk is on the plaza property, it would fall to the plaza's security guards to deal with.

Note that trespass by itself is not a criminal offence and the police have no power to enforce a trespasser's removal in the specific circumstances given by the OP, let alone arrest them¹.

¹There are some circumstances where trespass is an offence so an arrest may be lawful but I've not reproduced them here as they're off topic.

Community
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