The Yankees are having a bad season. In the rotation, CC Sabathia and Masahiro Tanaka have been great, but the offense has struggled far too often to score enough runs to hand a lead over to their dominant bullpen. The team isn't awful though, and that puts them in a position that good arguments can be made to try to acquire both young talent for the future and talent that can help them win this season.
This isn't a new position for the Yankees to be in. At this point of the season in the last two years, the team was in contention for the division or close enough to go after a wild card birth. The moves in June and July of both seasons show a pattern that might help predict how the Yankees will approach this season as well. Here are the major moves made during the past two seasons in the two months before the trade deadline.
Brandon McCarthy for Vidal Nuno and cash
Chase Headley for Rafael De Paula and Yangervis Solarte
Chris Capuano for cash
Martin Prado for Peter O'Brien and a player to be named later
Stephen Drew for Kelly Johnson
Tony Renda for David Carpenter
Dustin Ackley for Ramon Flores and Jose Ramirez
In both years, the Yankees made moves that could be classified as both buying and selling. In 2014, the acquisition of McCarthy, Headley, and Prado is a clear win-now upgrade. In 2015, Carpenter went to the Nationals for a second base prospect (side note: Renda eventually was involved in the trade for Aroldis Chapman.) Although Carpenter was struggling at the time, the move can still be considered a sell because Renda wasn't ready for the majors yet. In acquiring Ackley, the Yankees hoped to get a versatile, left handed bat that would help them compete for a playoff spot. They had wanted him for awhile and felt he could be a contributor in future years, too.
If this pattern continues in 2016, it is unlikely that the Yankees will commit to a full rebuild or a win-at-all-costs strategy. If the Yankees thought they were several years away from contention, they might consider trading everyone of value. Players with a lot of value would be traded for prospects. Aroldis Chapman, Andrew Miller, Aroldis Chapman, Dellin Betances, and Carlos Beltran would be traded quickly. Nathan Eovaldi, Didi Gregorius, and Starlin Castro might go, too. The Yankees would probably even consider giving away as much cash as it would take for a team to take CC Sabathia and try to convince Masahiro Tanaka to waive his no-trade clause. The team would then call up every prospect that could handle the majors and wait for them to develop while collecting high draft picks.
On the other hand, if the Yankees thought they were on the verge of competing for the World Series, they would start trying to upgrade at every position of weakness. Prospects like Luis Severino, Greg Bird, and Aaron Judge would be traded for an expensive first basemen, and third basemen, and a starting pitcher. Even players like Eovaldi and Michael Pineda, who have been on the active roster but are still developing, would potentially be traded for a veteran who is better right now.
Neither of these scenarios seem very likely. The best word to describe the Yankees recent pattern is opportunistic. When the Yankees have found an opportunity to upgrade their current roster for cheap, they've done it. When they've been able to acquire young talent for older players, they've done that too. As the season gets closer to the trade deadline and presuming they are not completely out of it, the Yankees will most likely make moves like this that put them closer to the playoffs while not giving up any top prospects.
At the same time, any player that is valuable and not under contract for next season, might be traded. Beltran and Chapman both fit this profile, and are probably the players most likely to be traded. It wouldn't be a surprise if the Yankees move either of both of these players in addition to acquiring younger assets who could help the team this season and in future seasons.