Going for a run makes no sense if you ask me. Same as taking that pick into account. It's gone, they should do what's best for the franchise going forward. If they have strong inclinations that neither of those three is interested in signing a long-term contract you need to think about long-term consequences. Sure they could catch lightning in a bottle and make a run, but at what cost? Is flirting with a playoff spot, or bowing out early in the playoffs worth risking either losing all three for nothing or selling them at the deadline for pennies on the dollar? And what if they repeat the horrible season? What if any of the three gets injured for long-term (happened to Stone this last season and Matt missed plenty of games in the past) around the deadline? Deciding to keep them going into the season is playing with fire if they don't have a contract. Again what they gave up in trades is water under the bridge and it should not influence how they operate going forward i.e. refusing to sell Matt for anything short of overpayment or sticking by him going into next season without a contract in place.
I know Sens fans will point to Matt saying he believes in the plan Dorion told him at the exit interview and that he likes it there, but after that happened an entire ****storm rained down on them and how much did Dorion really knew about the future state of the Sens given the uncertainty around not one but five (EK, Stone, Hoffman, Ceci, Anderson) key players not named Chabot or Duchene? Furthermore, this is a guy who said he wants to win and not waste his career rebuilding when he left Colorado. Sure he is close to home in Haliburton now, but how much does that really weigh in when he is a pro athlete who is on the road most of the time? Not to mention that he absolutely loved Colorado as a place to live in and still choose to chase wins over comfort in terms of a place to live in. I'm not saying this to pile on, this is just my realistic take on the situation.
PS
People will also point to the Avs in an attempt to say the Sens can make a dramatic turnaround. Can they? Sure. Is it realistic? No. The Avs overturned the vast majority of the roster. They had the 1st line explode and light the league on fire after the 10 game mark, they virtually added two top 4 D in Z and Girard, through trade and progression, added another D who has been instrumental in one of the best PK units in the NHL, got rid of cancers, dead weight and malcontents in the locker room in form of Iginla, Beauchemin, Colborne, Gelinas, Wiercioch, Grigorenko, Mitchell, Tyutin and replaced them with hungry young players like Girard, Andrighetto, Compher, Jost, Nemeth, Kerfoot ... And on top all of that had a goalie who performed really well when Varlamov was injured. Will Boucher be willing to play Brown, White, Botherson, Fremonton etc on regular basis? Will they move on from useless vets like Smith and co.