The decision to sacrifice a highly touted prospect’s potential rarely rests easy with a team’s fanbase, let alone its management, which assumes responsibility for each trade’s success or failure. The line between “going for it” and “mortgaging the future” is a narrow one, and GMs (understandably) often have trouble accomplishing the former without succumbing to the latter. A substantial amount of effort has been devoted to prospect valuation (though further work remains to be done), and as a result of that research, we can now attach an approximate dollar value to any given prospect’s pre-free-agency future. These figures don’t guarantee success, but they should make us stop to think before wantonly suggesting that a team trade one of its most valuable (albeit unproven) assets for a known quantity whose impact might ultimately make itself felt to a lesser degree.

We’re all familiar with at least a few prototypical “win now” trades from the past, which tend to be trotted out as each deadline approaches: Jeff Bagwell for Larry Andersen, for example, or John Smoltz for Doyle Alexander. In each of those cases, a team traded a top prospect for a quick fix, and the quick fixes worked out as well as could have been expected. Unfortunately for the teams that surrendered them, so did the prospects. Both the 1990 Red Sox and the 1987 Tigers qualified for the playoffs with two games to spare (thanks largely to the efforts of Andersen and Smoltz, respectively), but both clubs suffered early exits from the ALCS. Even division title flags can fly forever, but is raising one worth surrendering a Hall-of-Fame talent?

Of course, most top prospects exchanged for veteran help don’t go on to become franchise players at any point down the road. Fewer still go on to become productive performers without delay, immediately eclipsing the players for whom they were traded. When the Yankees dealt Austin Jackson (along with Ian Kennedy and Phil Coke) for Curtis Granderson last December, Brian Cashman succinctly expressed what one would presume to be the typical GM’s emotions after consummating a top-prospect-for-established-veteran swap: “We’re excited about what we're getting, and we're distraught about what we gave up at the same time. It’s not like I’m doing handstands. It’s a tough decision. You’re trading the future for here and now.”

Trading the future for the here and now may have been the Yankees' intent, but the swap hasn’t worked out exactly as planned. Had Jackson not been traded, he would have begun the season as the Bombers’ second-best prospect, according to Kevin Goldstein; he started the season ranked as baseball’s 76th-best prospect by Baseball America. However, his 2009 in Triple-A was marred by a distinct lack of power, and appeared to have been propped up by a .392 BABIP, giving rise to concerns that he wasn’t suited for a starting job anywhere in the majors, let alone for a strong contender. Meanwhile, Granderson was coming off of two consecutive seasonal declines, but still sported an impressive three-year average of 5.7 WARP. In short, this trade (which one wonders whether the Yankees would’ve chosen to make, could they have been sure of the emergence of Brett Gardner) had all the makings of an exchange that the team could one day come to regret, but that seemed unlikely to backfire anytime soon.

However, instead of reaping the rewards in the present, the Yankees have thus far come out on the losing end, even without factoring in the future value of the players involved. Put Kennedy and Coke aside for the moment; this trade occurred because the Yankees needed a championship-caliber center fielder, and (quite reasonably) didn’t think that Jackson was ready for prime time. With the first half and more completed (wouldn’t it be nice if each "half" actually comprised half of the season's contests?), the “here and now” has accumulated 1.6 WARP, while the “future” has 2.0 WARP to his name. For the Tigers, this has been the “Now and Later” of baseball trades, allowing Dave Dombrowski to relish some of the proceeds in 2010, while saving plenty for further enjoyment in subsequent seasons.

I don’t intend this as a critique of the Yankees’ decision to part with Jackson, which I didn’t deem ill-advised at the time, nor do I think that we should evaluate trading decisions based on their results (which shouldn’t prevent us from evaluating those results independent of the decisions that spawned them). I'm also confident  that the short-term results won't look quite as ugly from the Yankees’ perspective at season’s end: Jackson has been stellar on defense (though no better than Granderson), but although he may be a high-BABIP guy, as suggested by his career .361 minor-league mark, his MLB-leading .415 figure in that department is bound to fall (just as Ian Kennedy’s .267 BABIP and Phil Coke’s 2.1 HR/FB% are bound to rise), and his power has still failed to materialize. We also can’t say whether Jackson would have cracked under the strain of manning the position once held by the likes of DiMaggio, Mantle, and the illustrious Bubba Crosby had the Yankees thrust a starting role upon him this season.

All I’m really saying is this: what we’ve seen here thus far seems unusual. Teams don’t often trade away youngsters with no MLB experience for proven veterans with plenty, only to have those departed youngsters outperform the older acquisitions not just in the long run, but immediately. The Mark Mulder/Dan Haren and Matt Holliday/Carlos Gonzalez swaps might come close to qualifying as trades of this type, but at least Haren and Gonzalez had gained substantial major-league seasoning before they became trade fodder. Can anyone come up with some other recent (or not-so-recent) precedents?

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A classic would be the Cards' acquisition of Willie McGee for Bob Sykes in 1982. McGee was coming off his third season in AA in the Yankees' system, but was worth 0.8 WAR for the Cards in '82, while Sykes never played in the majors for the Yankees. By the time the Cards traded McGee in 1990, he had accumulated ~20 WAR in 9 seasons.
Bobby Abreu for Kevin Stocker is always the one that sticks in my mind. Abreu put up a 4.5 WARP versus Stocker's 0.9.