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Wade Redden, right, seen during a Rangers game this season, has a contract that has many observers wondering what Glen Sather was thinking when he signed the free-agent defenceman last summer.

Jim McIsaac/2008 Getty Images

The NHL's highest-paid player is the Washington Capitals' Alexander Ovechkin, but it's hard to argue that he isn't giving good value for the 13-year, $124-million (all currency U.S.) contract he signed with the team last year.

Not only does Ovechkin produce offence night in and night out, he also enthralls and entertains on pretty much every shift. Nowadays, any team that surrenders both term and dollars to players in contract negotiations wants a complete package in return.

Thus, no one begrudges Ovechkin his money; or Sidney Crosby or Evgeni Malkin theirs. And you'd have to think that the Detroit Red Wings are satisfied with the return on their investments in Henrik Zetterberg, Pavel Datsyuk and Nicklas Lidstrom, given that they are in the Stanley Cup final for the second consecutive year.

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Calgary is getting good value from the multi-dimensional Jarome Iginla at $7-million per season; and although it was Bryan Murray who drafted the pair in his days as the Anaheim Ducks general manager, Brian Burke did the organization a big favour prior to his departure for the Toronto Maple Leafs when he signed Ryan Getzlaf and Corey Perry to multi-year contract extensions with the identical (and attractive) salary cap charge of $5.325-million.

Burke never liked the fact that he needed to pay them those sums coming out of their entry-level contracts. On the plus side, both have evolved into big-time money players. In today's NHL, when you pay the talent at the highest end of your payroll less than $6-million per season on average, that leaves a few extra dollars on the table to pay a supporting cast.

Once in a while, these long-term commitments between team and player develop into a happily-ever relationship that works for both parties.

On a great many other occasions, however, the marriages don't work out the way they imagined - and the price of divorce is high.

In the next fortnight - or from the time of Friday night's seventh game of the Stanley Cup final until the first day of the entry draft in Montreal two weeks from now - NHL trade talks will heat up.

Increasingly, virtually every one of these possible transactions is going to be filtered through money, money invested in the flush of the last two free-agent frenzies that has not paid good dividends.

Contracts that were signed amid great hopes and expectations and - for reasons of injury, underperformance, or just the simple lack of a good fit - have backfired will now be shopped around the league, to see if there's a willing trading partner. Teams will need to get creative - and if the return that Ottawa eventually gets on the trade that Dany Heatley demanded this past month doesn't seem high enough, well, the answer will be found in the five years and $35-million that remain on his contract.

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But Heatley's isn't the worst - or the hardest-to-trade - contract in today's NHL. In the spirit of the-more-things-change, the-more-they-stay-the-same, the three most unwieldy contracts all belong to those free-spending New York Rangers, a team that couldn't figure out how to operate in the pre-salary cap NHL and a team that hasn't figured it out in the post-salary cap NHL either.

In an era when the salary cap will flatten this year and shrink next year, one man's view of the 10 worst contracts in the NHL right now.

1. Wade Redden, Rangers: His six-year, $39-million contract would not have been unreasonable compensation for an in-his-prime Redden who - for a five-year period between 2001 and 2006 - was a cumulative plus-123, while playing 25 minutes or so per night. But Redden's play fell off dramatically in his final two years with the Senators and everyone imagined he'd be looking at a hefty pay cut, until Rangers' GM Glen Sather came along. Don't these guys scout any more?

2. Scott Gomez, Rangers: Gomez's annual salary-cap charge of $7.357-million is ninth-highest in the NHL - he will earn $8-million in each of the next two seasons, before the numbers drop off to $7.5-million, $5.5-million and $4.5-million in the final three years of the contract. The Rangers signed Gomez, who led the league in assists in '04, to act as a set-up man for Jaromir Jagr, but the two never found any chemistry - and there isn't a pure sniper on either the current roster or in the system that would help maximize what Gomez brings to the table.

3. Chris Drury, Rangers: About the only saving grace with Drury's contract is its term - five years, which means there are only three years remaining. A cap charge of $7.05-million, any team interested in Drury would pay him $8-million in each of the next two years and then $5-million in the final year, a lot to pay for a player that has never scored 70 points in the NHL and conveniently managed his one-and-only season above 30 goals in his contract year with the '07 Sabres.

4. Brian Campbell, Blackhawks: At least, GM Dale Tallon was honest with reporters on the conference call announcing Campbell's signing, noting that he overpaid and saying: "On July 1, you always overpay." Did he ever. With an annual cap hit of $7.14-million for eight years, Campbell was, at best, a No. 3 on the Blackhawks behind Duncan Keith and Brent Seabrook, and had they been able to predict Cam Barker's improvement, might have given Campbell a pass.

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5. Shawn Horcoff, Oilers: His new six-year, $33-million contract is going to start next year with a $7-million payout, or what Iginla will earn with the Flames - too much in other words, for a player coming off a so-so 53 point season. Edmonton is paying him like a No. 1 centre - his cap number is higher that both Getzlaf's and Perry's - on contracts with similar terms. Presumably, Horcoff will get a chance to prove he is that under new coach Pat Quinn.

6. Daniel Briere, Flyers: The annual salary-cap hit is $6.5-million, but that's because the final two years of the eight-year, $52-million contract are cheap - $3-million and $2-million respectively. But any team interested in Briere's right would need to pay him $8-million and then three years at $7-million to get to that light at the end of the tunnel. Small and coming off abdominal surgery that limited him to 29 games, Briere will be difficult to move, and not just because he has a no-movement clause in his contract.

7. J.S. Giguere, Anaheim: With the emergence of Jonas Hiller, Giguere - a Cup winner in '06 - becomes superfluous in Anaheim; and if they could ever find a way of moving him, they might be able to hang on to Chris Pronger. Problem is, Giguere is the one player on the team with a no-movement contract - awarded by Burke for humanitarian reasons so the Gigueres could be close to the UCLA facility that treats his son, who was born with an eye disorder. Even if Giguere were to agree to the move, is there a market for a goaltender whose GAA jumped a full goal, year over year, who'll earn $6-million and $7-million respectively in the final two years of his deal.

8. Vincent Lecavalier, Tampa: Lecavalier differs from others on this list because he continues to play at an elite level, even last year when he was hampered all season by a bad wrist. The problem: An 11-year contract that kicks in on July 1, in which the first seven years pay him $10-million per season before steadily declining as it winds down (to $8.5, $4, $1.5 and $1-million). At 29, and with 10 full seasons under his belt, can Lecavalier deliver $10-million worth of production for the next seven years?

9. Ryan Smyth, Colorado: Smyth spurned the Oilers' 11th-hour contract entreaties back in the spring of '07 and found a willing buyer for his services in Colorado, who agreed to a five-year deal worth $31.25-million and an annual cap hit of $6.25-million. That's a lot to pay a heart-and-soul player who is not a true first liner. Three years remain on the deal at $6.5-million, $5.5-million and $4.5-million. With the Avalanche's fortunes declining, expect him to be an attractive commodity at next year's trading deadline if he is still performing well.

10. Ryan Malone, Tampa: Of interest because there was talk that Toronto might take on his contract in a possible swap for the second overall choice in the draft. Problem is, with a cap hit of $4.5-million and six years remaining at $4.25-million, it is a lot of money and term for a player with a career average of about 45 points per season.

FLYING BLIND: With the signing this past week of goaltender Ray Emery to a modest one-year, $1.5-million contract, the Philadelphia Flyers sent a signal on two fronts - that they are harkening back to their Broad St. Bullies days (brawling goaltenders actually came in the person of Ron Hextall in the mid-1980s); and that they will be a test case for fiscal prudence in an era when the NHL's salary-cap is about to flatten and then shrink.

Much of what the Flyers did correctly in executing a neat about-face in the NHL standings had to do with all the money GM Paul Holmgren threw at various free agents, a year after they finished dead last in the overall NHL standings. It worked too.

The continuing development of two young stars, Jeff Carter and Mike Richards, supplemented by expensive additions such as Kimmo Timmonen, Daniel Briere and Scott Hartnell fast-tracked their turnaround. In one year, they went from 30th overall to a spot in the Stanley Cup semi-finals.

Of course, all that's coming home to roost for the Flyers now, going into the 2009-10 season. Even before getting Emery to agree to terms on a new deal, they had $53.96-million committed to 16 players - and reasonably need to upgrade their defence by at least one top-four player.

Briere is probably not tradable. Simon Gagne had a bounce-back season (74 points in 79 games), although there'll be lingering concussion fears there. His contract is reasonable for his production (two more years at $5.25-million), but he has a no-trade clause as well. Joffrey Lupul (50 points in 79 games, but a defensive liability) is another player they could gladly do without - but again, for what cost? Holmgren clearly has his work cut out for him.

AS THE CROW FLIES: For a few years now, the NHL's Western Conference has had a few 'tweener' franchises - teams that did well for long periods of time, but inevitably became susceptible to the ebb and flow of pro sports.

The three teams that fit the category most prominently: Detroit, Colorado and Dallas, which dominated the landscape in the West for a decade. Detroit was able to sustain that excellence in the post-lockout era; last year, the bottom fell out on an Avalanche team that had clearly lost its way. Dallas stayed right on the cusp.

As recently as two years ago, the Stars made it all the way to the Stanley Cup semi-finals, and en route, upset a couple of heavy hitters, the Ducks and San Jose Sharks, to do so. Devastated by injuries and distracted by Sean Avery, they eventually ran out of gas in the final month and missed the playoffs - at which point new GM Joe Nieuwendyk gave the highly competent Dave Tippett his walking papers and replaced him with a far more risky choice, Marc Crawford, who has not been able to sustain the early success he had in his coaching debut with Quebec/Colorado in subsequent stops.

The Stars' thinking is clear: If their injured players all come back and goaltender Marty Turco proves that last year was just an off year, they could vault right back into the playoff picture with an experienced head coach who is tough on players and not renowned for his teaching skills.

It will be interesting to see if Nieuwendyk's first major move is an inspired choice - or fails miserably.

ETC ETC: Prediction for what happens next in Detroit: Marian Hossa signs a long-term contract extension, despite a so-so playoff. Jiri Hudler, Mikael Samuelsson, Brad Stuart and possibly even Tomas Holmstrom all leave, in trades, or as restricted and unrestricted free agents, opening up permanent spots for Ville Leino, Justin Abdelkader, Jonathan Ericsson and Darren Helm on next year's roster. Ken Holland wins his first annual GM of the year award, after managing his dollars so effectively … The larger mystery is what the Sharks do after finishing first overall in the regular season but stumbling out again in the playoffs. Heatley might be an option for them if Ottawa took Patrick Marleau in return. The dollars would be relatively comparable; and while Marleau had an effective 71-point season for the Sharks, the prevailing thought is that maybe they need a change in the captaincy to move forward . . . This just in: Ovechkin will be the cover athlete and spokesman for the video game, NHL 2K10. Some of the video that will be used in the game will be shot, outdoors, in Las Vegas, two days before next week's award show, on an artificial ice surface laid down at Caesar's Palace, starting at about 8:30 p.m. You hope the temperatures have dropped by then from an expected high in the 90s (Fahrenheit). Ovechkin is a Hart Trophy finalist; the Canucks' Ryan Kesler, a Selke finalist, will also be involved in the shoot.

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