So recent years got me thinking about the longterm vision and strategy to success, if recent WS winners had something had in common that could help the Yankees. There were different stragies and philosophies to winning, as teams like the Giants (Ace dominance), Royals (super bullpen), Dodgers (depth; platooning and versatility), Cubs (rebuild). As a copycat Cashman tried all those philosophies; acquisition of Cole, no runs BMC, signing of DJ to be utility and retooling to let the Baby Bombers play. This hasn't lead to a WS winner(or appearance) yet, but hopefully this can be the year. In some cases there were perennial LCS contenders involved; Dodgers, Astros, Braves. So what are the things they do, that makes them perennial LCS contenders? Of course there are multiple factors involved, but I'm going with the easy answer: they acquire (rental) talent that can make a difference for them in the stretch run and playoffs. The Dodgers did it with Machado, Turner and Scherzer; the Astros did it with Verlander, Cole, Greinke; the Braves did it with Pederson and Rosario, Greene and Melancon.
Besides that those players are difference maker, they also were acquired as a rental or for one and a half season. The costs (usually) for these type of players is lower than for instance; the Red Sox trading for Sale or the Yelich and Ozuna deals departing Miami. The result of the rental type of deals is that you can keep (most of) your blue chip prospects to infuse in your MLB team in the near future, and still manage to acquire (short term) MLB caliber talent to help your team, with the depth pieces in the system. In a way, we saw this tactic last year in the deals with Rizzo and Gallo, but that also had to do with the Cubs and Rangers paying down their salaries. So, if you don't acquire the players with multiple years of control the chance are, that you can keep your blue chips. However, because you can't keep them all, you need to identify where your strengths are in the system and which players are blocked to the MLB level, but still hold value to other clubs. So for instance, if the Yankees have any idea or indication that they can sign Judge longterm, they should trade their OF prospects close to the Mayors as they still hold value now in deals with other teams. If you want to deal them after you re-sign Judge, you lose leverage as the other team knows that the player is blocked. That could also be a sign to Judge' camp and other teams that you are serious in re-signing your star player.
Cashman tends to hug the prospects too much that they lose value. In case of Andujar and Frazier, both were exciting young talents who had a cup of tea and got injured. The team acquired other players in their absence or others stepped up, which limited their chances moving forward causing their values to slide. The Yankees need to avoid this same outcome with other promising players, who hold value now as trade chips but only as depth for Yankees. The Yankees have tons of talent, which can also walk out of the organization in the upcoming Rule 5 draft. They already dealt some depth pieces in the Benintendi deal. I expect some combination of Breaux, Weissert, Lockridge and/or Sauer to be dealt as they are eligible for the Rule 5 draft. I see them mostly as throw ins but these guys have some intriguing skillsets.
Cashman has already shown that he can work around the edges with acquiring talent which can be developed or triggered (Voit, Urshela, Trevino, Carpenter). So no need to worry about AAA depth. Now please step up to make the push for the World Series, because we've waited too long for (even an appearance in) the World Series! If not now, when?!
Side note: I wanted to add at the bottom that Cashman should have Hoyer on speed dial, as they have some intriguig players on their roster (Hendricks, Robertson, Hoerner, Effross) but they just traded for Effross. Maybe he could have a look in Cleveland then, on his way to Oakland.