Does it have a milky sap when you break off a leaf, like dandelions?

Welcome to RMG, Coach,
Skybird

Skybird, if you're hinting at milkweed, that was my first thought when I saw the picture as well.

It definitely has milky sap when it breaks on the stem...not sure about the leaves.
(it's like white blood...except sticky...I remember getting into lots of that as a kid...but can't remember which plant(s) it came from...milkweed I guess?)
:)

If it is milkweed...any ideas on how I can better control it?

I missed that you had come back with a reply, Coach! It sounds like you have some species of Asclepias! One of the common names is butterfly weed, and people pay money for the stuff you're trying to get rid of! Like dandelions, the seeds "float" in the air, and my guess is that some neighbor pretty close has one/some they're cultivating to attract butterflies! The most common species is A. incarnata--but I really have no way to know if that's the species that's showing up in your yard or not. Some info at the link below if you're interested in more!

In terms of getting rid of it, I recommend Weed-B-Gon. You can use that in the grass--it kills only broad leaf plants, and you can use it where there is no grass too. From my experience it works better than Roundup, and it's what I use anywhere I need an herbicide these days--works quite well at getting rid of cottonwood and aspen suckers in the grass! As far as I know all, or at least most, milkweeds have taproots, so the sooner you get rid of them the easier it will be. If you decide to try to pull them, you'll need to get all of the root out or they'll come back from anything you leave behind!

If you have a place where you want to grow some to attract butterflies (it's also a host plant for the caterpillars), you can just deadhead the flowers before any seeds form to help keep them from "filling up your yard!" Can't help with "the neighbor" if I'm right that that's where the seeds are coming from!

Skybird

P.S. The "plant" you were getting into as a kid was most likely dandelions!

Here is a link that might be useful: Asclepias incarnata