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Find one of the old Lincoln hand pump grease guns, they will put out 10,000 psi against a dead head. We used them for breaking the fittings and shackles loose on heavy trucks when they would not take grease from the air grease gun. They are easy to spot, with a long barrel and a long handle. You might find one in an old truck repair shop.
If you can get a helper with a long pry bar to jiggle the shackle bolt, this will help the grease to flow while you are pumping.
Consumer grease guns that are in the automotive stores do not put out much pressure.
I am guessing the fittings are pressed in. If you ever get the trailer jacked up, pull the bolts/pins, knock out the fittings, drill and tap 1/4-28 with a tapered tap, and screw in new fittings. If 1/4-28 is not big enough, just go bigger with the new fittings and tap.
Something to look for, in the past I have found "wet" shackles with fittings, but the bolt/pin was not through drilled for grease flow. A screw up in the manufacturing of the bolt.
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1999 7.3 F450 Cabriolet Crew Cab with Aluminum hauler bed (love the side storage!), Banks Power Pac, Donaldson Air Filter, Set up for Fifth Wheel, Gooseneck and bumper pull. ATS Billet Transmission, ATS Five Star Torque Converter, ATS Co-Pilot. Pulling a 34 ft. Silverado Aluminum Horse Trailer with Living Quarters.
This F450 will be replaced with a heavier truck, maybe a Freightliner or a Peterbilt around 25,000 GVW. AND with a big manual transmission.
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