The Red Sox have a bit of a 40-man roster crunch. A player who has to be protected is significantly less valuable to them. So Epstein says "Okay, you can have A or B." Cherington says "We prefer A, but he's Rule 5 eligible and we don't have a spot for him. Can you wait until after the draft? If he clears, we'll take him, otherwise B will do." But if A gets taken when otherwise the Cubs would have rostered him, suddenly they've lost A and B. Would they take that gamble just to pacify Boston? If they are offering him to Boston, then presumably they don't like him enough to roster him.