If it's like the 53MY rudder glands, yes it's a press fit which is so tight it holds itself up, and it's a pain because there is a flange around the top of the case which prevents you from reaching it from the top using a drift to get the old one out after it is cut. I think the guys that had set screws were for propshaft bearings, not rudder bearings. You said "cutlass" when you asked, which is only on a propshaft. You can't reach rudderports to put setscrews into them, because they're surrounded by hull. Here's what I did to fix the top flange access problem and replace my rudder bearings, which are 2" rudder shafts on a 53MY:
1. Buy a 2" propshaft bearing from SAMs and cut in in half (machine shop type cut, not a hacksaw, or at least file the edges perfectly). The rudder bearings are exactly the same as 1/2 of a propshaft cutlass bearing.
2. Remove the rudders, like you already have,
3. cut the old bearings in half with a sawzall, being careful about that top flange, which can break your saw blades when you hit it coming up from the bottom. Since the bearing to sleeve fit is not a moving part, it doesn't matter that you'll nick it a lot with the saw blade when it goes through the bearing. You do have to cut it on both sides or the bearing will be too strong to get out. At least one side has to be all the way through the bearing from top to bottom.
4. Drill a hole at the bottom of the bearing on one side, which you'll use to pull it down. After it's cut and drilled, it'll look like the picture "cut & drilled" below. If it's completely cut through on 2 sides, it may just fall out. I could only get it completely cut through on one side.
5. Use a punch or drift to lever it out a little, as in picture "punch removing". I hit the punch with a hammer after I had it set with a wood block to act as a lever. I only needed to get it out 1/4 inch.
6. Grab it with ViseGrips as shown and pull or lever it out.
7. Clean and smooth the inside of the sleeve. This is important! The press fit new one won't go in if there are any dings or cuts with edges or bumps sticking out past the original round tube surface. I just filed the cuts with a round metal file until the edges were below the sleeve tube sides. Also file and smooth the outside edge of the top of the new bearings a little so you can start them into the sleeves easier. Oil both the bearing and the inside of the sleeve.
8. Get a big honking jack, like they lift boats with. Put a big strong wood block on the jack and put the bearing on top of the wood block. Use the jack to press the bearing upwards into the sleeve. I put the original chamfered rubber ends down so it's easier to get the rudder back in the new bearing, but I don't think it matters. Be careful not to jack your boat off it's braces when you do this. The bearing takes a lot of pressure to press fit it in. It goes all the way in until it's even with the sleeve end.
Good Luck,
Doug Shuman