Pens fans keep saying that Crosby and Malkin have been given third line wingers, but to me the group of Hornqvist, Perron, Kunitz, Dupuis, and Bennett are decent wingers. Kunitz has slowed down this season but has been a bona fide top 6 winger for years. I'll admit Dupuis is both aging and injured, but come on, Hornqvist and Perron are legitimate top six guys, and Bennett would likely be one of not for all his injuries.
BB is the only legit winger Shero drafted during his entire tenure, and injuries have slowed him as you said. Shero obsessed over the blueline and never rounded out his farm with proper fwd depth.
Crosby played the last playoffs with an aging Kunitz and Gibbons as his wingers. This year he started the playoffs with Winnik, and then they switched Kunitz back there. Kunitz can barely handle the puck now and kills the play every time he touches the puck.
Malkin played with every third liner on the team this season before they settled on Comeau and whatever warm body they could give him. He went into the playoffs with a carousel of wingers, which was fitting for how the entire season went.
When the Pens won the cup, Malkin's winger were Talbot and Feds.
So yep, Malkin and Crosby have spent most of their careers playing with third liners and leeches (Kunitz/Neal) disguised as top six wingers. They have never had the benefit of playing with creative wingers that can carry the puck and generate offense on their own.
Hossa is the only legit creative winger either has played with their entire careers. That was for 2.5 months in 2008.