The Pittsburgh Penguins and their star captain Sidney Crosby have agreed to a new monster, 12 year $104 million contract. It keeps Crosby in a Penguins sweater for years to come, but is it worth it? The Penguins are investing a lot of money and time into a player that at any moment can suffer another blow to the head and end his career. Crosby is a great player when he is healthy, but those years, I fear, may be gone. It would cripple the team if Crosby doesn't play games on end if he gets hurt again because they have invested all this money in a very fragile player. Pittsburgh may have locked up their star player, but in the process may have hurt their chances at getting some depth and this roster and everyone knows that one player does not make a team. Another red flag is Evgeni Malkin. The reigning Art Ross and Hart Trophy winner will now want a massive $100+ million contract of his own. And he is completely deserving of one. More so than Sidney Crosby in fact. Malkin, for the most part, is a durable and reliable player. After missing half of last season, he only missed seven games this year and won the Art Ross and the Hart Trophies, while Crosby labored through another season with lingering effects from his concussion. The Penguins just don't have the money to afford two $100 million contracts and with the NHL's CBA ending this fall (Yes, another lockout is looming) and its going to squeeze the cap and I'm finding it hard to believe that both Malkin and Crosby could play on the same team with bloated contracts. It wouldn't surprise me in the least if Malkin gets traded before his contract is up. How often do 10+ year contracts work out well? Not very. It all started with Alexei Yashin and his 10 year, $87.5 million deal with the New York Islanders in 2001. Yashin's numbers declined and he never reached over 80 points in a season. You expect your big signing to put up some big numbers, but Yashin just couldn't do it. Yashin didn't even complete the entire length of the contract and spent up five seasons with the Islanders before he hightailed it to Russia. Yashin's Islanders teammate Rick DiPietro topped Yashin's contract with his own 15 year, $67.5 million deal with the Islanders in 2006. Ever since he signed that contract, DiPietro has pretty much been nonexsistant on Long Island. In the past four seasons, DiPietro has gotten only 14 wins. 14 WINS?! A lot of money to invest in what is now looking like a backup netminder. The list could go on and on. Mike Richards (not even in Philly any more), Roberto Luongo (can't win in the postseason and is a streaky player), Alexander Ovechkin (numbers keep going down every year), and so on. Pittsburgh may have put their eggs all in one basket with Crosby and its way too early to see if it'll work out, but I just don't see it ending very well for the Pens.