I posted this in another thread already, but I think it will be a worthwhile addition here as well.
If a deadline acquisition plays for your team, does not win the Cup, and leaves in the offseason, then you have lost your prospects and/or picks for nothing. Many teams make deadline deals every season, but ultimately only one team wins the Cup. As for prospects, the team has nine (Sproul, Ouellet, Tatar, Nyquist, Sheahan, Frk, Pulkkinen, Jurco, and Mrazek) that at present would be foolish to give away. As others have said---and it is true---this is a team that is rebuilding on the fly. Buying success is no longer possible. The teams that have won the Cup in the past four seasons have done so mainly on the strength of players whom they drafted and developed, and they drafted many of those players from high picks that were achieved from bottom-feeding seasons.
I'll list these players (first-rounders noted):
Pittsburgh (2009): Crosby (1st overall), Malkin (2nd overall), Staal (2nd overall), Fleury (1st overall), Orpik (18th overall), Letang, Kennedy, Scuderi, Talbot
Chicago (2010): Kane (1st overall), Toews (3rd overall), Seabrook (14th overall), Hjalmarsson, Keith, Brouwer, Byfuglien, Bolland
Boston (2011): Bergeron, Krejci, Seguin (2nd overall), Lucic, Marchand
Los Angeles (2012): Kopitar (11th overall), Brown (10th overall), Doughty (2nd overall), Voynov, Lewis (17th overall), Bernier (11th overall), Quick, King, Martinez
The above players, most particularly (italicized for emphasis) those drafted high in the 1st round, provided the meat for those Stanley Cup-winning teams. The contributions of Toews, Kane, Kopitar, Brown, Crosby, and Malkin require no explanation, and the highest pick used to select one of those was #11. For that matter, the lowest 1st-round-drafted player I listed above went at #18. In contrast, the highest pick that Holland has had (Kindl) since he has been with the Wings was #19. The highest pick that the Wings had before that? 10th overall... in 1991.
That's just how things go now. Want the Wings to remain successful? Great, but be aware that it'll come at the cost of never having any of these superstar draft picks unless KH and his team get very fortunate (as they often have). That's something the organization will always need to contend with. But in the salary cap era, it's doubly vital to develop the good prospects that the team does obtain. On that subject, consider if Datsyuk, Zetterberg, or Kronwall had been sent away as a part of a deadline deal when they were still prospects. This team would look very different now, almost certainly for the worse. And at this stage of time, KH can even more not risk sending away the next potential superstar prospect, because there's no longer the buffer of higher spending.
Like it or not, that's how it is. KH & company have been able to maintain the team's momentum since the lockout better than any other team in the league, but the system is constantly working against them in this.