I don't know how you could've missed it, but in case you did, the Ottawa Senators traded Shane Prince and a 7th-round pick to the New York Islanders in exchange for a 3rd-round pick in the dying minutes of trade deadline day. Thus ends a very strange tenure with the team. By all accounts, Prince should've been loved by the organization. He was picked up in the second round of 2011, Ottawa's biggest draft in a long time, and he played his junior hockey locally for the Ottawa 67s. He came to the Binghamton Senators as soon as he was eligible, and over three seasons increased his point totals from 35 to 48 to 65. That last season, 65 points led the Binghamton Senators and had him named to the AHL's second all-star team. In other words, he was named one of the best six forwards in the entire AHL for 2014-15.
There were also rumours following Prince. The big rumour was that he wanted an NHL contract, and if he didn't get one he would've bolted to the KHL. There were also rumours about a behind-the-scenes offer-sheet from Tim Murray for one of his favourite players to come join the Buffalo Sabres. But both of these past summers, Prince has said all the right things publicly and re-signed with the team.
The first sign that management wasn't so high on Prince came during last year's stretch run. Prince was called up for two games as part of prospects getting a chance to play down the stretch to show what they could do. Matt Puempel would get the next call-up, and he stayed for 13 games because the Sens weren't messing with a winning roster. When Puempel's season ended to a high-ankle sprain, Prince didn't get the spot. It confused many that Prince didn't get a shot despite playing better than Puempel in the AHL and the NHL.
This season, Prince started with the big club because he was no longer waiver-exempt. To not risk losing him for nothing, the Sens kept him up, just like Chris Wideman. Except Wideman has eventually managed to work his way into the team's long-term plans, while Prince has continued to get scratched. Prince had a breakout game in November against the Avalanche in which he scored two goals, and it looked like he was finally going to get his shot. But it fizzled out too. We've watched Puempel, Dave Dziurzynski, Max McCormick, Ryan Dzingel, and now Nick Paul all get called up and get more chances than Prince. We've watched Alex Chiasson continue to get played, sometimes on the Mike Hoffman line, despite his inability to handle a pass. Considering Prince led the team in 5v5 shot attempts, and was fourth in 5v5 points-per-60 (among forwards with at least 20 games), he probably deserved more ice and better linemates.
The big question this trade brings up was why it had to happen now. Probably the best-case scenario you can think of for a third-round pick is a player like Shane Prince: offensive skill, NHL-capable after a couple years in the minors, able to help out the fourth line or contribute in the top six. Prince will be an RFA for a couple more seasons, so it's not like he was going to be priced out of the team's range in a hurry. Even if his salary demands were ridiculous, his RFA rights would be as valuable in a couple summers as they were now. Last summer, the team traded Eric Gryba essentially for a fourth-round pick. Gryba was more of a sure thing than a fourth-rounder, but the Sens already had enough bottom-pairing defencemen. Conversely, with Clarke MacArthur out, Mike Hoffman was the team's only bona fide top-six left winger. After him, there were a whole lot of unknowns, and to me it makes sense to hold onto Paul, Dzingel, Puempel, and Prince in the hopes that one can consistently fulfill that role. The 3rd-round pick won't help the Sens for years, if at all, meaning the Sens now have fewer lottery tickets they hope work out in the top-six LW role. If the team's best shot at a Cup is any time in the next 5-6 years, Shane Prince would have been in his prime and could have been a contributor. If Dzingel and Paul passed him for sure on the depth chart in a year, not just based on a four-game sample, I highly doubt Prince's return would have decreased. It was unnecessary to trade Shane Prince this season.
I can only think of a couple reasons this trade makes sense. One is if Prince was disliked in the dressing room, and trading him was the best way to maintain cohesion. Another was if the team knew they were never going to play him again, and decided it was better to get something for him. I guess there's a possibility that he would've gone to the KHL after this season's treatment, but that's a pretty weak argument considering it's based on unproven rumours.
In the end, I don't get why you trade him for what at best is a wash, at worst is a huge loss. If the team needed to offload someone, why not Puempel who has been more disappointing in both the AHL and NHL and has a higher draft pedigree? Why not Alex Chiasson, who likely would've got a better return and reportedly was asked about but Bryan Murray refused to deal? I give this trade a solid D. It hurts the team short-term without likely having any kind of future benefit.