This past summer, I wrote an article about the cap consequences of the Reinhart trade. I thought it might be worth taking a look at how things have played out to this point for the players with bonuses, and how that might impact Chiarelli's thought process heading into the trade deadline. Now, without seeing the actual contracts it's difficult to know exactly which bonuses each player is eligible for, and exactly what the triggers are, but I'll list the bonuses it looks like each player has a reasonable chance at hitting. It's not impossible that others could be hit, but this is a look at those more seemingly attainable at this point in time.
Klefbom - max 350K in performance bonuses: He has a very good chance at hitting the TOI/game threshold provided he gets healthy enough to play in 42 games this year, and a half decent chance to achieve either of the plus minus bonus or the 0.49 points per game bonus. Could potentially max out his 350K, depending which bonuses he's eligible for.
Nurse - max 850K: Has a reasonable chance at plus minus bonuses and TOI. I don't think he would be voted for the all rookie team ahead of Gostisbehere or Parayko. Maybe 425K?
Reinhart - max 2.35M: He is unlikely to receive any performance bonuses.
McDavid - max 2.85M and Draisaitl - max 2.475M: Both of these players are grouped together as they have pretty similar outlooks relating to their bonuses. Both McDavid and Draisaitl look reasonably well positioned to achieve 3 or 4 of their Schedule A bonus triggers, with 4 likely hitting the limit of their 850K . The Schedule B bonuses are of particular interest. The only bonus that either player looks like they have a chance at hitting is top 10 in points per game among forwards BUT both have a decent chance. There is a minimum of 42 GP required, so McDavid in particular has to stay healthy, but McDavid is currently 2nd among forwards in points per game. Draisaitl is 12th and only 0.01 points per game behind 10th (Hall, interestingly enough). It's possible both could hit all their bonuses, which would be 5.325M combined.
There is a reasonable chance 6.1M in bonuses could be earned between the five players. So what does that mean? Well, that means the Oilers are looking at the potential for a significant overage penalty on their 2016/17 cap. According to general fanager, the Oilers are ~2.8M below the cap at the moment, so assuming that to be accurate, that nothing changes on the roster, and that those 6.1M in bonuses are indeed achieved, the Oilers would have a performance bonus overage of ~3.3M for the 2016/17 season. I would argue it doesn't make a lot of sense to keep an unlikely playoff team together if it results in carrying an overage penalty forward into a potential playoff season, so I think it would be a good course of action to dump as much money as they can prior to the deadline to avoid as much of that potential as possible*.
In terms of the deadline, the two players seemingly most likely to be on the potential trading block (making significant money) are Schultz and Purcell. It sounds like Edmonton will look to move Schultz, and assuming no money is retained that will save them some money against the salary cap. There has been some talk of keeping Purcell and signing him to a new contract for less money. In a vacuum I don't think that's a horrible idea, but the potential of a bonus overage charge changes the picture. It's not just choosing between keeping/re-signing Purcell and trading Purcell for a pick. If the Oilers move Purcell now, it probably saves them something like 1.3M against the cap, so keeping him and re-signing him for 2M (not a given he'd sign that, but let's assume he does for the sake of argument) might have an effective cost of 3.3M factoring in the potential bonus overage penalty that could have been reduced by moving him at the deadline. I think that means the best approach would be to move both Schultz and Purcell by the deadline. The earlier they are moved, the more cap space saved, and while retaining money to improve the quality of pick might ordinarily make some sense, I don't see that as being the best option here if either/both player can be moved without retaining salary, even if the quality of return is somewhat reduced.
* It would also save some money to carry 7 defensemen instead of 8. The combination of extra playing and development time in the minors with some cap space saved probably makes it prudent to demote either Nurse or Reinhart.
If money has to be retained in Purcell and Schultz trades, the Oilers might well choose to look at moving other players in addition to those two, at least partially in an effort to reduce potential bonus overages.