Detroit Red Wings: 7 Best Free-Agent Deals of Ken Holland's Tenure

He's been called many things over the past 14 years—a "genius," a "wizard," the "best GM in the NHL."

Since July 18th, 1997, Ken Holland has been at the helm of one of the most successful sports teams in the world over that same period of time.

Regardless of whether or not one thinks he's deserving of some of those aforementioned aliases, and Holland would be the first to point out that he's not, there's no getting around the fact that he's one of, if not the, most effective GM's in pro sports, let alone hockey.

As GM, Holland has to keep his finger on a multitude of things, all of which impact his team in significant ways.

From hiring coaches, to managing his own staff, to negotiating player contracts and making trades, there's not a single element of Detroit Red Wings hockey that Ken Holland doesn't have some influence or responsibility over.

Of all his duties, though, signing free agents is clearly the most outwardly glamorous of the bunch.

Though an internally exhausting and nerve-wracking venture, making a big splash via free agency is something that electrifies a GM's fanbase like nothing else.

It's the highlight reel goal of a GM's performance—it's only made possible through tireless effort and continual focus, but, once it happens, it becomes a magical thing.

Over the years, Ken Holland has made a lot of magic happen.

Sure, he's made some moves that went over about as well as a fart in church (Uwe Krupp anyone?), but, dollar for dollar, Ken Holland has made some of the best free agent decisions in hockey over the past 15 years.

As you might have guessed, I'm going to highlight seven of these, but, before we begin, you may want to take notice of a few things.

First, you'll find that some of the most iconic names that played under Holland's tenure aren't on here.

Yzerman, Lidstrom, Shanahan, Zetterberg, Datsyuk, Hasek...all of these players were either drafted by Detroit or acquired via trade.

Why point this out?

Well, the more cynical among us often accuse the Red Wings and Holland of "buying championships" by securing big names over the summer.

History suggests, hell, it confirms, this simply isn't the case.

Second, not all of the names on this list are of the marquee variety.

Often the best free-agent decisions fly under the radar when they're made, only to become huge parts of a team's success later on.  You'll find a few of these on this list.

Third, you should view these selections as a single collective of "best" free-agent signings.

I haven't ranked any of these, as finding any semi-objective measurement to apply to each of these is nearly impossible.

Slide 1 isn't supposed to be a "worse" signing than Slide 5.

They are all among the best signings Holland has made to date and, should any rankings be warranted, well, I'll leave that to you, the reader, to determine.

That said, I have arranged these in chronological order, starting from when Holland assumed his GM duties.

For the more tenured Wingnuts among us, that should tip you off as to who is coming first.

Can you guess?

No?

Here's another hint, restricted free agents are included in this group.

Still nothing?

Oh well, let's just get on with it.

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Sergei Fedorov, 1998

Talk about being tossed a grenade your first day on the job.

After 42 years, the last two of these utterly heartbreaking, the Detroit Red Wings finally secured the Stanley Cup in 1997, sweeping the Philadelphia Flyers in the Finals.

One of Detroit's brightest and youngest stars was Sergei Fedorov.

Given his new championship status, added to his Hart Trophy and double-Selke Trophy wins over the previous three seasons, everyone knew this impending RFA was going to be due a large raise.

That summer was bittersweet.

The horrific limo accident that robbed another young, bright star from the Red Wings, defenseman Vladimir Konstantinov, cast a shadow over what should have been the best summer of the Red Wings' lives.  And, somewhere in the back of everyone's mind, the question of Sergei Fedorov remaining a Red Wing was, well, a question.

Fedorov felt he was worth top-dollar, and stated he was willing to wait "a very long time" to get it.

He wasn't kidding.

The 1997-98 season started without him and, as October turned to November, and November to December, the idea of Fedorov ever playing for Detroit again became less and less believable.

The tension grew among the faithful.

Some hated Fedorov for being a "selfish, Russian diva."

Some hated the organization for just not paying the superstar whatever he wanted.

Time moved forward and so did the team, without Fedorov.

Then, in February of 1998, the Carolina Hurricanes announced that they had signed Sergei Fedorov to an offer sheet that would pay him upwards of $38 million.

Now, some rookie GMs would have taken this personal and seen this more or less as a "terminable offense."

It's conceivable that, in an effort to not be pushed around, or have someone else set his prices for him, Holland would have simply let Fedorov go.

Instead, he calmly saw this event as simply the market determining the price of a product and paid that amount to secure it.

Not only did that help get his team a second-consecutive Stanley Cup, it served to retain one of the greatest players in Red Wings history.

Steve Duchesne, 1999

Don't you laugh.

Before Holland signed veteran Steve Duchesne to a one-year deal in 1999, the Red Wings were set to have a top-three, rather than top-four, defense.

With Nicklas Lidstrom already firmly ensconced as the Wings' top d-man, veteran Larry Murphy his able partner and long-time nemesis-turned-new-best-friend Chris Chelios secured, the Red Wings had a pretty good stable of rearguards in 1999.

But, the talent dropped off sharply after that.

Mathieu Dandenault, Aaron Ward and rookie Jiri Fischer were all young, serviceable defenders, but none were truly top-four d-men.

With the acquisition of Duchesne, Holland added some veteran leadership, offensive ability and a bit of grit to his blueline.

Duchesne proved a valuable addition that year as he ended the season second only to Lidstrom in blueline scoring, thus securing an extended stay in the Motor City the following summer.

Duchesne contributed to the Red Wings' Stanley Cup win in 2002 and promptly retired a champion, making him one of the best, if not overlooked, free-agent acquisitions of Holland's illustrious GM career.

Luc Robataille, 2001

There's a few reasons Holland's signing of "Lucky" Luc was a great one and, I'll admit, some are personal.

First, the Los Angeles Kings icon was part of the reason Detroit's legitimate Stanley Cup hopes were dashed in 2001.

The seventh-seeded Kings pulled off the biggest upset of the playoffs when they dispatched the highly capable Red Wings in six games in Round 1 of the 2000-01 playoffs.

Now, being a guy who lives in L.A. but roots for the Red Wings, I endured a fair amount of personal pain and torment when this happened.

The Kings lost in the very next round to the eventual Cup champs, who will, for obvious reasons, remain nameless; but, beating the mighty Red Wings was a large feather in the cap of the Kings and their fans the rest of the summer.

So, when Kings GM Dave Taylor offered his most notable player a low-ball, one-year extension to stay on, some believed Luc would stay simply based on the momentum the team seemed to be building as a result of that first-round win.

So much for momentum.

Luc rejected the insultingly low offer from the Kings as well as a few, much higher offers from around the league to join the team he and his pals beat just months prior.

His reason?

Simply, he felt Detroit gave him the best opportunity to win a Cup.

From Holland's perspective, signing Luc was a measured risk.

If he came in and performed well en route to a championship, well then, he was a key part of what would be remembered as a team for the ages and the signing was a success.

If he flopped, well, who could have predicted that?  After all, Luc was more or less a living legend and when you've got a chance to add a guy like that to your roster, you take it.

Luckily for the Wings, and Luc, the former turned out to be the case.

The 2002 Red Wings are, without question, one of the greatest hockey teams ever built and adding a player of Robitaille's stature for less than market value was a great maneuver pulled off by that team's architect, Ken Holland.

Brett Hull, 2001

In his time as GM, Ken Holland has made some good, late-summer, "bargain basement" pick-ups via free agency.

Few remember that Brett Hull was one of these.

In late August of 2001, Brett Hull, who had played the past three seasons with the Dallas Stars, winning a Cup in 1999, was without a contract and without any serious suitors.

Later, Hull would say that it was kind of a nice break as it afforded him more time to do crossword puzzles which is why he said he was, "smarter than everyone else."

Still, he wasn't ready to retire, even if the rest of the league thought he was.

The Red Wings had already made some huge splashes, the biggest being the acquisition of goalie Dominik Hasek from Buffalo, followed shortly after by Luc Robitaille.

As constructed, the Wings looked set to take the most serious of runs at the Stanley Cup in 2001-02.

Then, a few friends got together at work and decided to ask their boss if a buddy of theirs could be offered a job.

They even said they'd take a pay cut to help bring their pal on, and even their friend would be willing to take on a smaller salary to take the job.

The friends, namely Chris Chelios, Brendan Shanahan and Steve Yzerman, convinced their boss, Ken Holland, to hire their pal Brett Hull given everyone's willingness to give up a little dough to get him, and that's how one of the most prolific scorers in hockey history became a Red Wing.

Like the aforementioned Robitaille, Hull was a key component of the Wings 2002 Stanley Cup win.

But, unlike Robitaille, who more or less withered away in his second year in Detroit, Hull became a key part of Detroit's future.

Before he left the team in 2003-04, Hull had taken under his wing and helped to mold young, quiet kids named Pavel and Henrik and helped turn them into eventual superstars.

Hockeytown would literally not have a "Hank," if not for Hully, who gave Henrik Zetterberg the Americanized nickname in the 2002-03 season.

As for Datsyuk, he still credits Hull to this day for making him a better player and acclimating to life in the NHL.

Run these names by Hull himself, and he'll beam about these two players, how blessed he feels to have played with them, how great it was to help mold them and how impressed he is by how smart they are.

He'll quickly add that they're not as smart as he is, but, they might be someday, if they start doing crossword puzzles.

Chris Osgood, 2005

I promise you, this isn't a sentimental pick spurred on by Chris Osgood's retirement.

I had this acquisition in the mix days before Osgood's announced his retirement on Tuesday.

Now that I think about it, that may make it even less legitimate to some of you, than had it simply been a nostalgic selection.

Honestly, bringing Osgood back to Detroit via free agency was a very savvy move on Holland's part.

After four years away from the Wings, Osgood, like the rest of the NHL, was without work and without prospects in 2005.

As the NHL resumed its existence in the summer of 2005, the Red Wings had just completed the "Curtis Joseph Experiment" to some degree of failure and had arguably the best backup in the NHL, Manny Legace, as their only No. 1 option in goal.

Aside from a league-wide 12-month hiatus, the Red Wings faced the uncertainty of new rules, new salary structures, a new roster and a new coach.

That's a lot of unknowns to deal with.

The largest of these was Legace, who looked to have all the skills to take the No. 1 job as his own, but had yet to do it.

Given all of these factors, bringing back a goalie who not only knew the organization and the players inside and out, but, having backstopped a Stanley Cup-winning team in 1998, was perhaps the best option Holland had in front of him.

Osgood appeared in 32 games for the Wings that season, winning 20 of them.

When the playoffs rolled around, there were some who felt Legace might not have what it took to win in the postseason and, with Osgood available, perhaps he should get the nod to start in Round 1.

New coach Mike Babcock didn't see things this way and, understandably, went with his established No. 1 goalie to start the playoffs.

What could have been we'll never know, but, given Legace's mental collapse against a shockingly underrated Edmonton Oilers squad, one wonders if the Wings would have had a better fate than their six-game loss had Ozzie been tending the net.

The 2005 signing of Chris Osgood ushered in the second Osgood-era in Detroit and, eventually, the franchise's 11th Stanley Cup in 2008.

Dan Cleary, 2005

Honestly, there's some question as to whether or not this free-agent signing can truly be attributable to Ken Holland at all, as it is Dan Cleary himself who actually made it happen.

After being drafted in the first round of the 1997 NHL Entry Draft by the Chicago Blackhawks, Cleary, who was touted to be a Patrick Kane-esque savior of the Chicago franchise, failed even to resemble a serviceable NHL player.

Possessing a tremendous amount of talent, but an underwhelming amount of work ethic, Cleary went from Chicago, to Edmonton, to Phoenix in the span of six years, with several stops in the AHL between them.

He was, it appeared, a poster-boy for failed potential.

As the Red Wings opened their post-lockout training camp, they invited several players to attend as tryouts and Cleary was one of these.

Interestingly, the Wings' new coach Mike Babcock knew Cleary from a previous coaching life.

When Babcock was the coach of the Canadian World Junior team in 1997, Cleary was a tryout then as well, until Babcock cut him.

With a few years of humility and a healthy does of maturity in hand, Cleary set about doing his best to make the Red Wings by convincing the coach who once cut him that he shouldn't do the same thing again.

It worked.

Cleary made the Red Wings squad out of training camp and was signed just as the season opened to a one-year contract.

Since then, he's been perhaps one of the most versatile forwards in the league.

He can play on any line, able to perform in an offensive or defensive role and has now become one of Babcock's go-to players, often praised for his work ethic.

That's quite a journey, and quite a pick-up, for a player and a team that began their relationship on less-than-stable footing.

Brian Rafalski, 2007

On July 1st, 2007, the Red Wings appeared to be in trouble...for about four minutes.

Established No. 2 defender Mathieu Schneider had just signed on with the newly minted Stanley Cup Champion Anaheim Ducks.

Schneider was a tremendous offensive-defenseman who had fit in perfectly with the Wings since he arrived to the team in 2003.

Losing a guy of his skill set and tenure was a much ballyhooed story on that first day of free agency.

It was said that Detroit's inability to retain a guy like Schneider could signal that they were "in trouble" next season.

Then, four minutes later, Ken Holland signed Brian Rafalski to a five-year contract and all that "trouble" talk went out the window.

Like Schneider before him, Rafalski instantly fit into Detroit's system and, along with Nicklas Lidstrom, proved to be the second part of a lethal power-play blueline.

Unlike Schneider before him, Rafalski didn't prove to be as great a defensive liability and used his positioning and speed to stymie the opposition.

Halfway through the season, many pundits considered him to be the best free-agent signing of the year.

A few months after that, it would be hard to argue anything but, as Rafalski raised the Stanley Cup over his head.

Though his retirement this summer was unexpected, when weighed against his recurring injuries and the tremendous amount of success he's achieved in the NHL, the timing seems just about right.

A few weeks ago, Ken Holland signed Ian White with the hope that he could sufficiently step into Rafalski's vacated role.

It's a tall order, but, with any luck, we'll see White on a list like this in a few years.