I am having a gardener trim a tree on my property. If I have him sign a waiver and release of liability should any problems arise as I safe?

No, A person cannot waive their legal rights. If the gardener is injured because of your negligence, a waiver won't prevent him suing. That's why you should only deal with someone that carries insurance.

There are two types of liability here:

your liability should he or third parties be injured; and
his liability in case you, your property, or third parties be injured.


Make sure the release covers both (although, as ScottGem said, it is questionable whether that would completely shield you), and that his insurance does the same.

Generally when you hire someone who is self employed to do work on your property, you ask for a state license number for that profession (so that he is on file on a publicly accessible database, for one thing) and for proof of his own liability insurance.
Many one person operations have neither, or only the license, because insurance is very expensive. You will pay a lot more for that.
I don't think that a waiver will do much good in court if he is injured on your property and uninsured.

I work these case all the time. No, a release does not protect you, same as a release when you have a trampoline or (even more bizarre) a sign in your car that you are not liable for injuries to your passengers. Yes, I've seen those.

In NY the homeowner is also responsible for providing a safe working environment. I've investigated a number of "tree" guys and roofers, painters, who fall from various heights and the homeowner bears some responsibility, among other things, for an unsafe work environment. I've discussed the situation more than once - I'm not a roofer. You are and you tell me this is what you are going to do and how you're going to do it and I'm supposed to know if that plan is safe? Unfortunately, the law does not agree with me.

What do I do? I carry a rider on my homeowners' insurance that covers people who do work for me, however casually, I never pay off the books, I make sure they are licensed (if necessary) and insured (with proof) so that they don't get injured and end up living in my house (tongue in cheek).

Yes and the relationship of how they are hired, as a employee, as a contractor can all make a difference of how far that liability can go.

Our church ( many years ago) hire a man to mow the grass using our mowers. He fell off the mower, got part of his foot cut off. He sued, Church, the maker of the mower and I believe the church member who had hired him.
He got paid for his injury, any money he lost while he could not work and more.

Had they hire a company who had insurance including workers comp on employees, that would not have happened.