It depends. Let’s fast forward 5-10 years. Did the guy with the failures just fly the line and go home? Or did he use those years bettering himself, both personally and professionally? Did he volunteer for union positions? Did he volunteer in his community? Did he gain leadership roles in each of those activities? Did he attend safety and professional development seminars and apply them to his flying? Did he earn more type ratings, or get through another initial or upgrade without a hitch? Did he earn airline accolades like Instructor/LCA/CP, etc? Did he earn any awards, from either his company, the FAA, or both? Does he have stellar recommendations from people around him? Does he own up to his failures? And does he have no additional failures since?
If yes, then absolutely, I’d take the guy with the five failures. Especially if they were at the beginning of his career/primary training.