I have no idea if Brian Cashman has ever seen Pirates of the Caribbean or its sequels, but it is a hard thing these days to be a Yankees fan and not be obsessively thinking about Pirates. Although there are four teams which have interest in A.J. Burnett, it's the Pirates who have garnered the most attention. Since both Brian Cashman and Neal Huntington have been general managers of their respective teams for some time, we can take a look at a past trade the two conjured together, but why does a past trade matter? The answer is that much of the time, no matter how important a trade might seem at the time, it ends up being insignificant—good teams remain good, bad teams remain bad. It is seldom, if ever, that any one player can change his team's fortunes that much. For instance, consider the trade that sent Xavier Nady and Damaso Marte to the Yankees for Jose Tabata, Dan McCutchen, Jeff Karstens and Ross Ohlendorf.
The trade in question occurred in July 2008, and although the Yankees were immediately considered deadline winners, the trade was not successful enough to get the Yankees over the hump; as of today, 2008 remains the only season since 1995 in which the Yankees have not made the postseason. The Pirates were non-contenders in 2008; though they had a successful first half last season, they are still considered non-contenders by most, although, in finishing fourth last season, they may not be quite as hapless as they once were.
If we break it down further, looking at what has become of the various players involved, it becomes much harder to say that the Yankees won the deal.
In terms of a bust, it's hard to find a bigger deadline one than Nady. He'd had a brilliant first half in 2008 for the Pirates, but his second half with the Yankees was, well, not good, at least, certainly not good enough to justify the price paid for him. He was supposed to be the starting right fielder for the Yankees in 2009, but injured his throwing elbow in the season's first two weeks and would eventually need Tommy John surgery. Had someone other than Nick Swisher been the Yankees' back-up right fielder at the time, Nady might have gotten another chance, but Swisher was simply too good. Nady played just seven games for the Yankees in 2009; 66 in pinstripes total; he has since played for the Cubs and Diamondbacks.
The funny thing here is that the year before Marte was traded to the Yankees, the best available reliever was traded to the Red Sox, a trade that proved to be as close to a disaster as any such trade can be for a team that goes on to win the World Series. In some ways, Marte proved to be remarkably similar. While Gagne's career with the Red Sox was derailed by post-surgical ineffectiveness, Marte's days in pinstripes were curtailed by injuries; even after signing a three-year extension after the 2008 season, Marte only appeared in 76 games between that year and 2010. Marte's saving grace, if it can be called such, is that the Yankees, good as they were, might not have been able to win the 2009 World Series without him. If you wanted to debate whether the mantra "flags fly forever" is a perfectly valid reason to excuse any other on-field shortcomings, Marte could be your test case.
Originally one of the non-pitcher jewels of the Yankees' re-stocked farm system, Tabata's major league career got off to a hot start, but he was nothing spectacular in 2011, and his off-field life has involved some rather bizarre stories. He was also coming off a suspension for leaving the team without permission. While the Yankees probably weren't expecting Brett Gardner to become their everyday left fielder at the time, they haven't exactly missed Tabata, either. Tabata's still young—only 24 this season; even though the trade is now four seasons old, the Pirates may still have yet to reap all of the benefits their outfielder might offer.
Rated by Baseball America as the team's 14th-best prospect, the profile in that year's Prospect Handbook remarked on McCutchen's "aggressive" demeanor, and that there was no overall consensus as to whether he would end up as a starter or reliever. After acquiring him in the trade, the Pirates tried him first as a starter who made his major league debut in 2009. The experiment resulted in him almost pitching himself off the roster last season, and McCutchen's team has only belatedly switched him to long relief. He had some more success in that role, but he'll turn 30 this year, making it unlikely the Pirates can expect anything more out of him in terms of development.
If Karstens' career with the Yankees is remembered for anything, it will be for throwing five pitches, and then walking off the field with a broken leg. In that sense, Karstens was perceived as the anti-Pavano, but he too could not stay healthy in pinstripes. As a Pirate, Karstens has been more successful with each passing season, though in this case 'success' is relative: for some pitchers success might mean a Cy Young; for others it might mean staying healthy and an ERA below 4.00.
Ross Ohlendorf is still smarter than you. The former Princeton scholar had limited time with the Yankees at the major league level, but had some success in Pittsburgh in 2009 before injuries began to get in the way. He missed 62 games with a combination of back injuries in 2010 that bookended the season; a shoulder injury last season caused him to miss 108 games. Ohlendorf might have been the most promising of the three pitchers that were sent to Pittsburgh, but unrealized promise will remain just that if one can't stay healthy.
The Yankees may not have lost any All Stars in the four players they sent to Pittsburgh (the jury's still out on Tabata), but the reason they lose the trade here is because, whatever their struggles, with the exception of Ohlendorf, the acquired Pirates have managed to stay on the field, giving their team something. The Yankees did get a World Series ring with both Nady and Marte on the roster, but the former didn't appear on the field after April of that season and the latter managed a giant contract (for a reliever, and a LOOGY at that) that he couldn't fulfill.
Of course, as Marc Carig tweeted, it's a topsy-turvy world when the Yankees are looking at the Pirates to take on some salary relief, instead of the other way around—which was primarily the circumstance involved in the Pirates being willing to trade Nady and Marte in 2008. The Pirates could and perhaps should be better than the Cubs and Astros in 2012, but even if they did add Burnett, whether or not they could actually contend for the NL Central crown would still be doubtful. The Reds and Brewers will still be good, and the Cardinals managed to win the World Series even without having Adam Wainwright available.
On the other hand, the Yankees, with Burnett on the roster or without, would still be favored to win the AL East. The team would still be on the hook for the majority of Burnett's remaining salary, so the cash relief would only be so much, but an available roster spot is not always easy to come by.
The Yankees and Pirates have been around the majors long enough to have traded players with each other since 1915; Willie Randolph might be the single biggest name involved in any one of those transactions (a historic steal for the Yankees in which they got an all-time great second baseman, Dock Ellis, and Ken Brett for Doc Medich) . A Burnett trade would garner attention simply because of the size of Burnett's contract and the appearance of a reversal of fiscal fortune, but barring a sudden change in Burnett's pitching ability, it's probably not going to be a deal that moves mountains. The Nady/Marte deal was considered the biggest trade at the deadline when it happened, but the fortunes of the teams involved were not altered in any significant way because of it. CC Sabathia, Nick Swisher and Mark Teixeira were much more important to the Yankees' 2009 title than Marte was, and the Pirates are still waiting for their first .500 season since the original George Bush was in office.