Or actually make it from metal and make it adjustable.

This is probably your cheapest option OP. Just bear in mind that as the column continues to sink, the angle between the gatepost and the bricks will get more and more obvious.

Maybe a retaining wall a few feet away to at least prevent more leaning? Unless it's frostheave causing it, in which case the foundation just wasn't deep enough.

I like compression, and would have wooden or steel beams suporting the front side. A set of two on angle, so as to not overly interfere with zippers.

Well I assume that the hill is subsiding and slowly taking the column with it. I am sure the weight doesn’t help. I’d sort out the hill first in terms of drainage and perhaps a retaining wall. That is all pretty DIY. I think the right answer for righting the column is the folks that inject mud underneath. That will be pricey. If you are able to stabilize the hill and the column isn’t so bad as it is now, there may be less drastic things you could do to level the gate and or slightly right the column.

Mud jacking is the term

Well, it probably isn’t a real good idea to DIY, but if I were to give it a go, I’d rent a mini-backhoe (lots of companies in the US rent these, not sure where you’re from). I’d dig down and around the footing, then I’d use the backhoe to push the column into position to hold it there while filling the hole with additional concrete. Probably $700 or so and two days effort. But, again, not sure I’d try this. Lots to go wrong.

My friend had some driveway sections leveled, and it turned out great. This would be a lot heavier, but I'm sure the experts know what they're doing.

How heavy is the gate? Is it 1 gate or 2? Is it the weight of the gate pulling the pillar?

can you give us a close up of the hinges and how far the pillar is out of plumb. (using a 4 foot long or longer level, measure the distance from wall at the top of the level when held plumb). that will help in giving you some recommendations.

i am assuming its a steel gate. whats the length

Not the worst idea, though I'd paint it black to make it look like part of the framing for the gate.

Maybe he's thinking it's one of those anti-grav gates?

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It’s leaning away from the gate…that’s definitely not the cause. And the weight of that gate is inconsequential to the brick column.

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foundation and concrete leveling people are your friend here. I wouldnt DIY a 1/2 ton column of stone and concrete

The weight of the gate (more relevant, the bending moment exerted by the gate) is overturning the column.

Maybe fix a wheel to the end of the gate and install a quadrant track for it to run on. No more weight that's overturning the column, the weight is supported by the wheel.

You can sleeve the cable in pvc pipe or something.

I am not sure if you are in the US or where in the US, but $14k is very decent. Not only they have to build a new brick column, foundation and supports, the have to make sure to match your fence perfectly or it wont work. Maybe try to get other quotes but be careful on scope of work.

I would try with the foam companies but how are they going to match it to level and work with the electric gate? it will be very tricky.

Fancy things have fancy prices... good luck bro.

Cheap way would be to mount a piece of wood on the bricks, paint it to look like the bricks, then mount the gate hinge on that.

Check with a concrete leveling company. I know in a neighborhood near me, they used foam injections under several stone columns to correct leaning.

Wait a couple hundred years and market it as a tourist attraction

Appreciate this. I can adjust the drop with placement on the tree and the eventual termination platform. I'm just guessing at the drop right now anyway but will make proper calculations prior to eventual construction.

Oh, I see. This pole needs to be at the top. I'd still build a platform if I'm taking on a project like this. Even if it's only a platform 2 or 3 feet off the ground.

The start point doesn't need to be any higher so that doesn't need a landing platform (I'm in hill country so have plenty of fall already). I did plan to build a platform at the termination point though, but that has a tree so platform infrastructure doesn't give me anything I do not already have. Its the origination point that is tree-less.