I own a Winchester model 1885 chambered for the "long" cartridge case and was given some cartridges loaded on the "short" case.
I'd like to just go ahead and shoot them as is without pulling bullets and eloading into the longer cases.
What's your opinion of my doing this?

I have a CPA with the longer chamber and shoot Winchester cases in it, and they are of the short variety. Only problems I have had is a little leading. I wouldn't worry about shooting those loads as long as they are not loaded to extreme velocity.
Sam

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Best practices dictate that one should never shoot someone else's reloaded ammunition, .  .  .  unless and until, you are given and receive accurate and reliable information from the reloader as to what propellant and in what quantity it was used in the reloading process.

The 38-55 case is a black powder cartridge from the 19th century.  Your Winchester was manufactured 130 years ago.

Might I suggest that you use your press with the 38-55 shell holder installed and no die. Then run the case up, grasp the bullet in locking pliers (vise-grips) then lower the cartridge, thereby extracting the bullet.   

Next, empty the powder charge into your scale pan, making sure you have captured the entire contents.  Weight it, and most importantly, identify which propellant it is.

If you are not 100 % certain as to what powder was used, without asking or relying on the reloader, then proceed to dis-assemble the entirety of the donated 38-55 cartridges.

Safety always comes before convenience.

I agree with the Dr. Better safe than sorry.

These cartridges were given to me by a close friend and an accomplished reloader who provided me with the data he used to load the cartridges.
I have shot them in my near-hundred year old 1894 Winchester over a chronograph with average velocities of 1650 fps with no pressure signs.

There is NOTHING like something blowing up to get you attention!