The Yankees currently have an 9.8% chance of making the wildcard game and a 3.7% chance of winning the division. The season is not over, but the odds are heavily stacked against the Yankees in 2016. Whether or not this should be surprising is an interesting topic to debate, but we should probably accept it as fact at this point. The Yankees are far from the best team in the AL East, and it's obvious.
The last time the Yankees were in a similar position was the 2013 season. In the middle of July, they were hovering above .500, six games back of the Red Sox and Rays. There was hope, but not a lot of hope. They possessed arguably the best hitter and reliever potentially on the market at the trade deadline in Robison Cano and Hiroki Kuroda. Instead of selling, they bet on another miracle playoff run. It failed. Instead of jump starting their rebuild, the Yankees have been limping along with an old roster full of overpriced free agents ever since.
The Yankees have another chance to jump start their rebuild. They will go into the trade deadline with arguably the two best relief pitchers, the best starting pitcher and the second best catcher on the market, along with a bunch of other complimentary pieces. Arguably, they have the best portfolio of sellable assets among non-contenders in baseball., While the Yankee farm system is looking reasonably productive, it isn't going to produce a winning team (even complimented with free agents) on it's own in the near term. The Yankees need reinforcements.
What is the alternative? The roster as currently constructed is not going to make the playoffs in 2017. The free agent class is weak. Other than Gary Sanchez and Greg Bird, there are no imminent young players coming up by Spring Training. Other than Brian Cashman crossing his fingers and praying to Lou Gehrig, there is no plausible route to building a playoff team this season or next. An infusion of young players will allow the Yankees to reset and prepare for future free agent classes.
The Red Sox followed a very similar plan after their 2011 team fizzled, and they built a powerhouse on it. The Yankees have more money than the Red Sox have right now, and arguably better trade assets than they did in 2011.
Who Can the Yankees Trade (and get some return)?
The easy ones
Let's start with the easy ones, barring some unforeseen event in the next 30 days, in a rough order of trade value: Masahiro Tanaka, Dellin Betances, Andrew Miller, Aroldis Chapman, Brian McCann, Nathan Eovaldi, Ivan Nova, Andrew Miller, Carlos Beltran, Brett Gardner. Unlike in 2013, the Yankees have a bunch of guys performing reasonably well on decent contracts.
All of these guys are either old or will reach free agency before the next chance at a Yankee contender with the exception of Dellin Betances. Should Betances be on the trading block? Assuming he fixes his current funk, Betances could be a valuable member of the Yankee bullpen through the 2019 season. However, Betances is older (28) than he seems. His best years are probably behind him. He has real long term value though, so the Yankees should probably wait to pull the trigger for a decent return.
In my book, every player here should go, either at the deadline or early in the offseason.
The under-performers: Pineda, Castro, Gregorius
At least three Yankee players have crushed our hopes and dreams this season: Michael Pineda, Starlin Castro, and Didi Gregorius should have been a part of an effective young core. Collectively, they have been worth -0.1 bWAR in 2016 so far. All are on reasonable contracts and have enough talent for an interested team to work with.
When is the right time to trade someone like that? On one hand, if they continue their current track, they each hold more value now than they will in the future. On the other hand, they could turn it around and be more valuable (both to the Yankees long term and on the market) in six months. I think I stand pat if I am Cashman, unless some team blows the Yankees away.
The Contract-Eaters: Ellsbury, Sabathia, Headley
I think the Yankees could trade any of Jacoby Ellsbury, CC Sabathia, or Chase Headley if they are willing to eat some of the contracts. Ellsubry, as Dave Cameron argues today, has actually been pretty good in 2016. When not playing injured, he's proven to be about a 4-win player at this stage in his career. Arguably, that justifies his salary, although teams will price in some decline. I don't know what the Yankees would have to eat to get a team to take him, but have plenty of outfielders in the system to take his place.
Sabathia and Headley are more complicated. Sabathia is grossly overpaid for this season and next, but is probably an improvement in a number of contending rotations. I'm looking at you, Detroit and Pittsburgh. Headley has just been bad, but has been improving over the last month, and could look like an upgrade to some teams with bad third base situations if the Yankees take most of the cost.