Booger, if you can't kill them with a 270, you aren't likely to do better with a different caliber.
603, unless I completely missed my guess, it sounds to me like he did kill both deer ...they just did not drop DRT..... one ran 200+ yards .....
I shot a doe one time that when hit, ran close to 300 yards before slowing to a walk, walked in a circle and lay down ...... upon field dressing, I found that the bullet had punched a neat hole in both shoulder blades right above the joint with the upper leg bones, and had trashed both lungs and the large vessels atop the heart ..... she was dead the moment she was hit, but it wasn't until her brain ran out of blood pressure and O
2 that she was convinced of it ..... another, similar sized doe, just a year later, with the same rifle and load, at a similar range, hit the ground so fast I did not see her fall, and thought I had missed ......
I hit a nice buck at a range of about 15 yards, broadside and splattered a goodly portion of both his lungs on a tree behind him- the exit wound made by the 150gr SGK was big enough to put 3 fingers in- he went over a hill a good 150 yards and piled up ..... but he was easy enough to find ...... again, very dead, but running until he could not ....
I hit a button buck (led him a bit too far) as he was running by at a range of maybe 25 feet - he kept right on running until he hit a tree a couple of bounds later .... and fell down and kept right on running, legs furiously pumping the air as he lay on his side ..... I ran up and put my revolver to the base of his neck and hit the off switch .... and then noticed that my shot from the rifle had hit him in the head, blowing most of his brains out the side that now lay on the ground ...... again, very, very dead, just not aware of the fact.....
Then there's the other extreme - this year's buck (probably the biggest bodied deer I've ever taken) dropped to the shot, I doubt he knew what hit him- hit high behind the shoulder, the bullet passed through the very top of the lungs and just across the bottom of the front end of the loins/backstraps .... I've hit deer there before and had to track them quite some distance ...... but he said, "Nope, I'm done. Night-Night." BANG! (flop)
You just never can tell ...... all these were with a .270 WIN and a 150gr SGK ..... but I doubt that the caliber mattered all that much ..... though the first two does I mentioned were out past 400 yards, so hitting them with something ..... not as flat shooting as the .270WIN might have been a bit trickier .....