GM 2500 and 3500 have 8 lug wheels, all the newer Escalades i have seen have 6 lug (light duty)1500 axles. If you have 8 lug wheels than its an H/D, with H/D suspension. I have never seen one, not saying that its not possible though. Also if you have the standard Escalade versus the ESV that is a short truck. I wouldn't pull the boat your talking about, its not the actual "will it pull it" but the "can the truck handle stopping, turning and an emergency if needed".

Truck most times will determine the boat.

Way too much boat for a escalade. Any 4 cylinder car could move it. It's the stopping and turning you have to worry about.

Pretty sure GM never made a 2500 Escalade. Even if it did, I think it would only be rated at 10k like the Suburban. (Yes, previous generation was 12k with towing package, but no longer offered). Those ratings are there for a reason and in reality, it really should be hauled with a diesel pickup.

I think there's a video out there somewhere of a Tundra pulling a space shuttle, but unless you plan on going 20ft at 2mph on a dry flat surface, I wouldn't attempt it. A wet ramp is all you need to lose your Escalade. With your current vehicle, I wouldn't be pulling anything bigger than 27-28' or you might find yourself in some hairy situations more often than not.

Check with your Ins. company, bet they tell you that you won't have Ins when towing. Check your hitch limits, I would think you will be over that also.

All that and you will most likely damage the "Auto Ride Air Suspension" the first time it tries to level out the hitch load.

NO way. You need a minimum 3/4 ton truck. That setup is definitely over 11,000 lbs, on the trailer, likely over 12K.
All that weight behind the axles (fulcrum) of the trailer will whip that SUV (and it's contents including your family) all over the place, especially with that spaghetti suspension rear end.

Can it? Yes.

Should it? Probably not.

Joe- I dont think it has the 2500 frame and axles. That would mean 8 lug axles. The Escalade is a rebadged Tahoe/Suburban 1500.

The Suburban 2500 has the upgraded frame and axles. Your Escalade will pull it, stopping and control is the issue. Good Luck!!

Took a while for your "no tow" radar today lol.