There's a couple of reasons, I think: Managers and GMs largely want to limit doubt as much as possible. With unproven young players, there's doubt as to whether they can perform at the ML level. With a Punto or Miles, you have certainty. You know you're not going to get great numbers, but you also feel comfortable that you know the level they'll produce at and, therefore, eliminate doubt from that position. If you fill that position with an unproven player, you question whether he'll produce worse, the same or better than the veteran and for a GM/manager (especially one whose job is in doubt) that's a bad thing. Second, many managers value intangibles because they provide security. "Winner", "gritty", "plays the right way", "smart", "does the little things" are all comments you'll hear from managers describing players like Punto and Miles. It can't be proven that those intangibles exist, but you also can't prove they don't exist either, so it's easy for a manager/GM who has been brought up believing in those things to fall back on them when they sign an unproductive player. Since many fans also buy into those as legitimate attributes, those moves become highly popular among the fanbase and upper management (who also largely believe in those things), thus providing even more security for the manager/GM.