While working on the C&O under the Chessie banner I transfered from the Big Sandy SD to the Cincinnati SD..After completing my required student trips to qualify I was called to protect the job as a head brakeman on a transfer run to a rail to barge trans-loading facility at South Shore Ky about 30 miles from the Russell yard.This should be a piece of cake-easy money.Take the loads,drop them off,pick up the empties and return to Russell. The engineer and I went to get the unit consist while the conductor and rear brakeman was taken to the train.The first sign of trouble was the unit consist make up..We had 3 Chessie GP40 the lead unit was a B&O unit..We would need to switch that out as a B&O unit could not lead on C&O track due to the signal system in the cab unless it had the C&O type of signal pick up in the cab which this unit did not.It had the straight B&O signal pick up(apparently this unit was a trailing unit on a train off the Northern SD or the Cincinnati SD) we switch this unit out and made it the second unit in the consist with a C&O unit on both ends.The DS,conductor and rear brakeman was advised of the new lead unit number.After coupling on to our train pumping up the air and making a inspection we was ready to high ball and that we did after getting clearance out of the yard and lined up for the main. We made it as far as the first bad dip in the track about 7 miles out of Russell -then WHAM! the train goes into emergency.Well nothing to do but walk the train to see what happen..The rear man would begin his walk from the caboose..About 73 cars deep we found a air line pop loose.Ok..No real problem so we thought. Before recoupling the cars we noticed that the coupler on the both cars was CLOSED!!! What?? Ok,so I open the coupler and told the engineer to ease her east and was good for 12-14 cars before making a joint.We made the joint and notice we had about 1/4 of a coupler doing the work due to a very low coupler on the car we just coupled on to.. Well,Lets try it and see what happens we might make it to South Shore.Again the air was pump up and the train was inspected..Off we go.2 miles down the line outside of Greenup Ky-WHAM! back into emergency.Again the same problem this time the conductor came to look over the situation.Not please he radioed the DS and told him about the problem and that he would like to sit the car off at Limeville so the carmen could fix it..No dice-if you are that close to South Shore after you get to Limeville you just it take on to South Shore. So we repeated our steps as above and headed off on down the line and made it as far as Limeville before we went back into emergency.Well the old conductor had enough of this problem..He started to walk down the track..He was gone about 20 minutes before he return carrying some spikes.He said, Larry left up on that coupler and I will fix the problem.The rear brakeman had been sent to protect the rear of our train.The conductor wedges the spikes in the coupler box under the coupler and raised the height of the coupler where we could make a fairly good joint and that we did..We finish the run without any more problems and return to Russell in about 9 hours..If all went well we would have returned in about 4 or 5 hours depending on Limeville(the junction where the Cincinnati SD,the Northern SD and the Russell SD join together) and getting clearance into the yard. The Russell SD runs from Limeville to Russell.