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I just did that today!
I just repaired the antenna on my wife's '87, which should be similar to yours. Because I didn't know what the problem was (the antenna would extend only one "segment" before stopping), I removed the entire assembly so I could take it apart. Also, the rubber seals were damaged/missing so they had to be replaced.
After I took the assembly apart, I figured out that the problem was a jammed mast, so I replaced the mast with a new one. Once the antenna was working properly, I put the thing back in the car, which is where you are now. I replaced both the "lower" and "upper" rubber seal pieces.
First, I pushed the "lower" piece through the body of the car, pushing the seal from the outside towards the inside (sounds backwards) until the sheet metal of the body fit into the groove in the rubber seal. Next, I pressed the top part of the seal onto the lower part until the top popped into place on the bottom.
The antenna cable screws onto its socket and the power wire plugs into a socket on the antenna. Connect those before putting the antenna in place as it's much easier to get at them first. You can also test the antenna before installing it. Connect the braided ground wire to the car body with a clip lead and have someone hold the antenna so the mast doesn't get stuck on something as it extends. I hope your wiring has survived intact!
Then I carefully inserted the antenna into the rubber seal (from the inside of the trunk) and slowly pushed it through, rotating it back and forth to help it go through without popping the seal out of the sheet metal. You might want to put a little soap-and-water or Armor-All on the rubber to help the mast slip through smoothly -- I didn't have to do that.
The mast is far enough through when the bracket (has a captive nut) on the bottom of the antenna assembly lines up with the hole in the inside of the body. A screw holds the bracket to the body. That's the only thing that holds the antenna to the car -- that and friction. The antenna is at a 20 or 30 degree angle leaning back -- it's not straight up and down.
There is another captive nut up near the top of the antenna, which is for the braided ground wire. Attach the ground wire to the captive nut with a screw.
That's all there is to it. I apologize for failing to take pictures.
Jeremy
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"Buster" in the '95
Our all-Diesel family
1996 E300D (W210) . .338,000 miles Wife's car
2005 E320 CDI . . 113,000 miles My car
Santa Rosa population 176,762 (2022)
Total. . . . . . . . . . . . 627,762
"Oh lord won't you buy me a Mercedes Benz."
-- Janis Joplin, October 1, 1970
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