I didn't find anything on the search but I'm sure it has been answered before.
I pulled the rubber out of the chrome track at the rear of my driver side window. I can't get it back in without messing it up.
Does in slide in from one end or do you have to compress it to get it back in the track?
I even tried using some soap to lube it up.
Any tips or tricks would be appreciated.

No sliding...

Put one side into the chrome then use a blunt object to push the other side into the chrome.

Quick and easy.

Thanks Andy. I guess when I tried that technique my object wasn't blunt enough. I will give it another go in the morning.

I find Silicone spray works great for installing rubber weather strip.

I did this little job awhile back. IIRC, it looked like the factory intentionally dented the channel a little bit to hold the seal in place. I straightened out these dents a bit before putting in the new seal. I used a silicon lube on the seal and a wall paper seam roller as my "blunt object". Start at the top or bottom and use the seam roller to press the seal into place. I think it took me about 15 minutes to do one door-glass-to-targa-pillar seal. You could carefully "dent" the channel to hold the new seal in place but it seemed like such a tight fit that I did not do this.

I've done mine a few times, if you have a problem bring it by I'll give you a hand.

Jeff

I would recommend glycerine over silicone. Glycerine (can still be found at your local drug store) helps condition rubber, while silicone actually helps the rubber degrade over time.

--DD

Just don't use the glycerine over nitric acid, that would be bad!

Alright here is the answer to my question if you need to squeeze 40 year old rubber back into its channel use a window screen roller. It worked perfectly. No lube or blunt object needed. Once you get the right angle and pressure it zipped it right in with one continuous pass. Simple. I knew there was a trick! Thanks toadman yougot me the right track with wall paper seamer technique. Click to view attachment Click to view attachment

Nice.
Yes, rubber has memory, stretch it with vibration and hot/cold cycles, it will shrink back.