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in every jurisdiction i'm aware of you do not have to be a formal employee to be considered an agent/servant/representative/under the control of a business. in a lot of construction litigation the contractor, subcontractor, reality trust, and property management companies end up as defendants for this very reason (thats why most of their contracts have subrogation clauses).
Big difference here is that we're talking an intentional tort and not a construction defect type case where it isn't clear whose faulty work among a cluster of contractors/subs whose work is closely intertwined caused the defect at the outset of a lawsuit. While independent contractors are, like employees, agents of the person who hired them, scope of their agency is extremely attenuated as compared to a conventional employee because of the legal nature of that relationship. The general rule remains that independent contractors use their own discretion in how to complete the work they were contracted to perform. So, in the absence certain rare exceptions, there is no liability by one who hires a contractor for the contractor's negligence. That goes double for intentional torts, which require the extra element of ratification (advance approval of the tortious conduct or failure to subsequently address it) before holding employers liable for employee's conduct while in the course and scope of employment. So at minimum, the slim chance that Thrasher/High Speed ratified the conduct would be required for liability, and that's assuming he were to be considered an employee (even more unlikely).
The case against the building is bad, too. He's almost certainly an employee of a contractor who provides security services for the defendant building/property management, he's aware that altercations are possible in the course of his job, and the duty to warn, if any, would likely fall on his employer. Since his employer is a contractor of the building/property management company, they (very much by design) aren't liable for the acts of independent contractors any more than Thrasher/High Speed. Vieira is the low-hanging fruit, but he's judgment proof and the judgment could or would be discharged in bankruptcy anyway.
I'm just spitballing and could be mistaken about something important, but still, I see lots of reasons to feel bad for this dude and his prospects of getting any money this way. Even though I would quite literally be out of a job if it were any different, this is why civil lawsuits and liability insurance are no substitute for a nation simply treating its citizens humanely by providing for their essential needs through generous social programs.
there are plenty of examples of a a party being held liable for an intentional tort committed an independent contractor:
bar/bouncer cases, Uber assault cases, sexual harassment cases, day cares & summer camps, private security cases, really weird malicious destruction of property claims that sounds like movie but are not.
if the depositions break right i actually really like the case against the building. plus strategically it makes a ton sense. i would have made the same call.
Sure, it happens, but it's even less common than employer liability for employee intentional torts, which is already fairly uncommon. At minimum it would take establishing an increased degree of control over the contractor sufficient to make them a de facto employee and foreseeability that the tort might be committed.
I suppose the best shot is liability against the building, since they might have directed the security to do something specific regarding skateboarders, but like you said, that's why good discovery is really important there. I think it's a reach against High Speed/Thrasher, since it's not clear how exactly Vieira is legally tied to them or GX for that matter, but that's small potatoes compared to the building.
And none of this is to say that he won't see a payday, just that the best outcome is to find an angle early and settle against the parties with good liability policies before they drown him with motion practice.