Pittsburgh vs. Detroit: Who has the better general manager?

Puck Daddy's Sean Leahy and Greg Wyshynski are previewing every facet of the Stanley Cup finals between the Pittsburgh Penguins and the Detroit Red Wings -- on the ice and off the ice. You can find all of our Stanley Cup Playoffs coverage here.

Every Stanley Cup team is built in a different way. Some are built on toughness (2007 Anaheim Ducks), some on defense (name any New Jersey winner) and some on phenomenal offense (any Edmonton club from the 1980's). It's the job of the general manager to piece together the parts in order to have a deep, successful run in the playoffs. It's a job with long hours, some stress, plenty of worry, and a job that could make one have plenty of sleepless nights pondering a completed or potential move.

Ken Holland and Ray Shero are very much mirrors of their own teams. Holland is the veteran here in his 11th season as Detroit GM. Shero is only in his second season as GM of the Penguins. Both have taken different routes that have found themselves head-to-head in the Stanley Cup Finals.

After being an assistant GM with Ottawa (1993-98) and Nashville (1998-2006), Ray Shero was ready to make his mark on the National Hockey League. He took over a Pittsburgh club coming off a 58-point season, but with a lot of young talent and promise. Oh, and a kid named Sidney Crosby as well. His first draft pick was Jordan Staal, who has become a solid third-line center at the tender age of 19.

The draft was not a crutch on Shero or the Penguins. From their tough times between 2002-2005, they stockpiled top draft picks that later developed into core players like Brooks Orpik, Ryan Whitney, Max Talbot, Marc-Andre Fleury, Evgeni Malkin, Kris Letang, and Tyler Kennedy. It would be the free agent and trade market that Shero would piece together a Stanley Cup contender.

It began with the signing of pest Jarkko Ruutu, continued with a trade for bodyguard Georges Laraque, and ultimately came to a head at the beginning of last summer.

There's an old adage that when a new GM is hired, the current head coach doesn't stand a chance. Shero didn't think twice about bringing in his own guy. He saw the amount of change that the Penguin organization was going through and decided some sort of stability was needed, keeping coach Michel Therrien. Last July, when Shero extended Therrien's contract through the 2008-09 season, it was a stamp of approval as well as a reward for a coach who guided his team to a 47-point increase in 2006-07.

The son of the legendary Flyers coach Fred Shero, understood he had a special team in front of him and locking up certain players would be key to a long, successful go at the Stanley Cup. He locked up Ryan Whitney to a 6-year deal, Sidney Crosby to a 5-year extension, brought in underrated MVP of the season Ty Conklin, and stole Petr Sykora off the free-agent market for a mere $2.5 million a year. Sykora contributed 28 goals and 63 points this season on the wing.

With the Penguins in the middle of a mid-season revival thanks to the work of Conklin and the emergence of Evgeni Malkin in Sidney Crosby's absence, Shero made his biggest splash at the trade deadline and threw a warning shot across the Eastern Conference and NHL: Pittsburgh was making a big-time run at the Cup.

After weeks of speculation that Marian Hossa was going to Montreal and here and there and everywhere, it was the Penguins that acquired the Atlanta forward on Feb. 26, along with Pascal Dupuis for a heavy price. In giving up Colby Armstrong, Erik Christensen, prospect Angelo Esposito, and a 2008 1st-round draft pick, Shero understood that in a salary-cap era, you don't get many chances at the Stanley Cup, but he was doubted by many pundits who said the Penguins gave too much for a rental player.

Right now, the Penguins are four wins away from raising the Stanley Cup. Somewhere, those doubters might be proved wrong over the next two weeks.

While the Ray Shero molded the Penguins through the free agent and trade markets while already having a deep system thanks to the NHL Draft, Ken Holland and his scouting department deserve medals for their work in finding players through the Draft:

Pavel Datsyuk, 6 th round, 171 st, 1998
Henrik Zetterberg, 7 th round, 210 th, 1999
Johan Franzen, 3 rd round, 97 th, 2004
Valtteri Filppulla, 3 rd round, 95 th, 2002

Detroit has only one first-round pick under Holland's command since 1997: Niklas Kronwall, who was drafted 29th in 2000. The Red Wings roster is full of bargains in this day and age of big contracts. Zetterberg is on the books for $2.7 million this season and $2.9 next season before becoming a free agent in 2010. Tomas Holmstrom, the crease crasher himself, makes a mere $2.25 million for two more seasons. "The Mule," Johan Franzen, who had a coming-out party through the first three-rounds, is earning $1.15 million this season. Finally, Chris Osgood might be the biggest bargain of them all with his $800K contract for this season.

Holland knows how to build a squad, create that locker room and on-ice chemistry by adding the right guys, and keeping them in Motown with the lure of being Stanley Cup contenders every season. Over the years, he's brought in guys like Brett Hull, Luc Robitaille, Dominik Hasek, Chris Chelios and Robert Lang, and they've all won in Detroit.

When the NHL implemented the salary-cap beginning with the 2005-06 season, everyone thought that would the end of the Red Wings as perennial contenders. The team also lost stars like Brendan Shanahan and Steve Yzerman to free agency and retirement, respectively. "No way could Detroit just throw as much money around that they wanted anymore" many thought.

Guess again. With tremendous drafting and keen free agent signings (Dan Cleary, Dallas Drake, Brian Rafalski) three years running they've won the Central Division and the President's Trophy two of the last three seasons. Just when you think Detroit is dead, they get stronger and stronger.

And that's to the credit of Ken Holland.

ADVANTAGE: Detroit. Holland is a three-time Stanley Cup winner and has been able to keep the Red Wings successful despite the salary cap. His ability to find quality players in the later rounds of the Draft gives him the edge here. Shero is just getting started and his biggest challenge is yet to come: keeping this Penguins team together.