Greetings,
Are you referring to the hole for the #61 Taper Pin?
If so, the #58 Column Shaft and #60 Crank Shaft Bearing would have been machined as a noninterchangeable unit.
If you were forced to use repair parts from non-matching units a #7 Taper Ream "may" clean up both pieces and a new taper pin installed. Here again, the alignment of the machine would have to be maintained. Just running a reamer to clean up the holes is not an adequate fix. The repair would have to be done on a milling machine where the parts can be clamped in proper alignment.
This may be a repair for Cunningham, if he has the proper jigs from the old factory.
Cheers,
Dave