With Anthony DeAngelo‘s demotion to Hartford, the June trade the New York Rangers made to acquire him doesn’t look so promising after all.

On June 23, 2017, the New York Rangers traded center Derek Stepan and goaltender Antti Raanta to the Arizona Coyotes for defensemen Anthony DeAngelo and the 21st overall pick in the 2017 NHL Entry Draft, which turned out to be center Filip Chytil.

As of this afternoon, both DeAngelo and Chytil are in the AHL playing for the Hartford Wolf Pack. This is not how the team thought things would go when the summer began.

Chytil had a great training camp for the Rangers and he won a spot on the opening night roster. After two games and little ice time, he was sent down to the AHL. The speed of the NHL game seemed to be too much for the 18-year-old, and the organization felt some time in the minors would help him gain some confidence as he adjusted o the North American style of hockey. He was injured this past weekend and his status remains unclear.

DeAngelo has struggled throughout his time with the Rangers. He played in eight games, recording one assist and was a minus-4 on the season. He played the part of a seventh defenseman in each of the past two games and only got on the ice when the Rangers were on the power play.

As for Stepan, he is having a good start to his career in Arizona, scoring two goals and four assists in eight games. One of the team’s assistant captains, he’s averaging 20:46 of ice-time and his faceoff percentage is at 47.9 percent.

Raanta, meanwhile, has gone 0-1-1 with a 3.33 goals against average and .911 save percentage in three games for the Coyotes.

So how does the trade made back in June look today? Not great.

Sure, the success or failure of a trade doesn’t appear immediately. Chytil could turn out to be the steal of the deal. He has all the tools to be a great NHL player, but for now, he’s just another prospect. DeAngelo was always the question mark of this deal. The Rangers are the third team he has played for in his short career, and the issues that many pointed out before—a lack of confidence and poor decision-making—remain.

It’s unclear what the future is for DeAngelo. Being sent down to the minors could benefit his development for the future or it could be a permanent move on a team that is already strong at the defense position. He could also be even less motivated by the demotion.

The Rangers start to the season at 2-6-2 is unacceptable. They had to do something in an attempt to improve the team so that they can get back to winning hockey games. This is probably not the last move to be made as the team didn’t really improve. Perhaps they are making room for another player to join the team, either from recalling a player from the Wolf Pack or by making a trade.

Coincidentally, the Coyotes will be in town to play the Rangers at MSG on Thursday night. The only players involved in that trade who will take the ice—Raanta and Stepan, the guys the Rangers traded away.