How many times do you hear announcers say the winning team won because they wanted it more. But "wanting it more" often just becomes synonymous with weird bounces that come your way, giving the impression of extra-effort and more desire.
I always cringe at that comment.
I think the only question really worth asking is, has Dipoto used his available resources (salary/prospects) to put together a team that can win on a consistent basis, over a series of years? If we win 87 games, missing out on the WC on the final day of the season, only to win 76 games each of the next two seasons, then where are we?
Segura, Haniger, Gamel, Vogelbach, Ford, Gordon, Marco, Healy were all short, mid and long-term acquisitions, or ideally so. Some of those guys cost use S-M-LT guys to get them. Ultimately, the proof is in the pudding: Dipoto at least needs to deliver in the short and mid-term areas. Did he pick the right talent, trading lesser players for more?
If not, he's gone in two years.
Everybody wants to win (even Derek Jeter "wants" to win this season), but if you're not making best use of your resources then you're relying a bit on more than a bit of luck. I can't find much overall fault with Dipoto's use of MiLB prospects, simply because the jury remains out (Tank vs. Marco, for example), but I can whine if I feel he hasn't grabbed impact players (that fit) off the FA list. MLBT-R reported today or yesterday that we had made a 3-yr bid for Jon Jay, and only when he rejected it did we go out to grab Gordon. If that is the case, then Dipoto was lucky, then good....all at the same time.