Part of being a shitty team that is ascending is cutting ties with marginal talent that the fanbase and the team get attached to.
I will use the Blues as an example. in 2006, the Blues were the absolute laughing stock of the league. Horrible attendance, worst record in hockey, and rapidly declining as our talent got older and more oft injured.
The team featured guys like Eric Boguniecki, Peter Cajanek, Lee Stempniak, Ryan Johnson, Jay McClement, and the list went on and on. However, the Blues used high draft picks to draft the TJ Oshies, David Backes', Jaden Scwartzs, David Perrons, and Vladimir Tarasenkos and slowly but surely the team was pruned of the marginal talent for actual talent.
Austin Pettis is a throwback to those bad teams. He was there for Sam when no one else was, but now he needs to be pruned for superior talent. Sure, Lee Stempniak scored a few goals for the Blues, but he was eventually traded for Alexander Steen, a guy who is a bona fide star in the NHL now.
Its hard, it sucks, but for this team to continue to ascend, guys like Pettis need to go away and real NFL players like Stedman Bailey need to take his spot. Its all part of the game.