“Show Me The Money!” is not a worn out catch-phrase, where high profile free agents are concerned.

Every summer, the elites in NHL boardrooms pony up big dollars to sign free agents of quality — as well as dubious over-achievers.

Some years produce great finds on the open market, while others, like this year’s crop, are long on past-their-prime stars.

Who, then, will be this year’s free agent busts? The Leafs signed soon-to-be 38-year-old star Patrick Marleau to a rich, three-year $18.75 million deal. He was indicative of the greybeards available and will join the kiddie corps in Toronto with visions of rejuvenating a career on the downslope. We believe it won’t take long to see if this deal is boom, or bust.

The Leafs weren’t alone, either, handing cash to aging former superstars.

Since summer free agency became more of a thing in the 1990s, numerous teams have rolled the dice on expensive talent and come up snake eyes.

Here are who we consider to be the worst summer free agent signings ever, in no particular order.

15. Kelly Hrudey – San Jose Sharks 1996

The Sharks were still trying to find their footing in the summer of ’96 and needed a no. 1 goalie to supplant de facto starter Chris Terreri, who struggled mightily in 1995-96. Hrudey, a good but not great netminder, was coming off two OK seasons with the Los Angeles Kings, who he had played with for eight seasons and went to a Stanley Cup final with in 1993. Already 35, Hrudey was inked to a two-year, $5 million contract, which was pretty good money then. As it turned out, Hrudey would be strictly mediocre in Sharks’ teal. During his first season, he posted a 16-24-5 record with a .889 save percentage and 3.19 goals against average. The Sharks missed the playoffs, too. In 1997-98, Hrudey lost the starting job to Mike Vernon and registered a 4-16-2 mark and .897 save percentage. He retired immediately after that season and is now a talking head for Hockey Night In Canada.

Source: goaliesarchive.com

14. Sean Avery – Dallas Stars 2008

Past practice is the best indicator of future behavior, or something like that. The Dallas Stars should have thought twice in 2008 about signing super-pest and oft-maligned winger Sean Avery to a rich four-year, $15.5 million pact in the summer of 2008. Sure he brought plenty of grit and a knack for smack talk to a Dallas line-up in need of some sandpaper, however, he was never a big scorer and the 33 points he put up in 57 games with the New York Rangers in 2007-08 was an aberration. Former Detroit Red Wings roommate and then co-GM Brett Hull could be blamed for this blunder, too. Avery played all of 23 games, scoring three goals and seven assists along with a whopping 77 penalty minutes. He was suspended for six games for yet another foul-mouthed transgression that he was notorious for, leading to being put on waivers in February, 2009.

(AP Photo/Tony Gutierrez, File)

13. Chris Gratton – Philadelphia Flyers 1997

In the early 90s, Chris Gratton was a prototypical big centerman who could score and throw his weight around. The Tampa Bay Lightning drafted the sizable native of Brantford third overall in 1993 and watched as he slowly matured. By 1996-97, he recorded career highs in goals (30), assists (32), points (62) and penalty minutes (201). Philadelphia was only too happy, then, to sign the free agent in the summer of 1997 to a huge five-year, $16.5 million contract that included a $9 million signing bonus. As Gratton was a restricted free agent, the Flyers had to surrender Mikael Renberg and Karl Dykhuis to the Bolts to complete the deal. He performed admirably in his first season in the City of Brotherly Love, matching his point total from the previous season. He chipped in two goals in five playoff games, too. The bloom came off the rose in 1998-99, when Gratton managed just eight points in 26 games and was -8. He was promptly dealt back to Tampa midway through that campaign.

(AP Photo/Dan Loh)

12. Sheldon Souray – Edmonton Oilers 2007

Buyer beware should have been ringing in the ears of Oilers management in 2007 when they though about signing Elk Point, AB native Sheldon Souray. A good, but not great defenceman with size, Souray was coming off a career year with the Montreal Canadiens in which he scored 26 goals and 38 assists in 81 games. However, he was defensively deficient, also posting a career worst -28. Yet, they signed the 30-year-old to a massive five-year, $27 million contract. His first season, Souray was often injured, playing in just 26 games, with 10 points and a -7 rating. He gave the team hope by turning it around in 2008-09, logging 53 points (20 goals) and a +1. The injury bug bit again in 2009-10, when a concussion and hand injury limited him to 37 games. He registered 13 points and was a dismal -19. A bun fight ensued about how the Oilers handled his injury and eventually he was waived, never to return.

THE CANADIAN PRESS/Darryl Dyck

11. Martin Lapointe – Boston Bruins 2001

The Detroit Red Wings thought enough of rugged right winger Lapointe in 1991 to draft him 10th overall after several great seasons in the QMJHL with the Laval Titan. As has been the team policy with most players, he percolated well in the AHL with Adirondack before finally sticking with the big club in 1995-96. Lapointe started slowly but built enough momentum to score a career high 27 goals and 57 points (+3) in his free agent year of 2000-01. The Bruins, seeking a shooter down the right side that they lacked the season previous, ponied up for four years and $20 million — something owner Jeremy Jacobs rarely did. In quick time, Lapointe became known as one of the most overpaid players in the league. For that princely sum, the Bruins got 40 goals, 43 assists and a -12 in 205 games.

(CP PHOTO/Aaron Harris)

10. Bobby Holik – New York Rangers 2002

We’re not sure what Glen ‘Slats’ Sather was thinking in the summer of 2002, but it must have been muddled with hubris. After missing the playoffs in five straight seasons and seeing his Blueshirts take a licking on the scoreboard and in the corners, he figured his best bet was signing big, but aging center Bobby Holik. The solid two-way player put up solid but not spectacular numbers (472 points and a +134 in 786 games) and won two Stanley Cups with the New Jersey Devils before hitting free agency that year. Sather figured five years and $45 million for a 31-year-old pivot sounded about right. How wrong he was. Doomed to fail, Holik had 35 point in 64 games in his first season, and the Rangers missed the post-season again. He managed 56 points in 82 games the next season to redeem himself, yet his team again failed to make the playoffs. Seeing enough, Sather bought out the three remaining years on the pact.

(AP Photo/Shawn Baldwin)

9. Cristobal Huet – Chicago Blackhawks 2008

Perhaps it was the novelty of signing a goalie from France and the fact he was actually decent during the 2007-08 season that clouded the judgement of Hawks’ brass in the summer of 2008. Cristobal Huet, a native of St-Martin-d’Heres, was quite good in a 2007-08 season split between Montreal and Washington, recording a career high in wins (32) along with a 2.32 goals against average and .920 save percentage. Believing he might be the answer to a 47-year Cup drought, Huet put his signature on a whopping four-year, $22.5 million contract. In the first year of that deal, he allowed Nikolai Khabibulin to get the lion’s share of games, going 20-15-4 with a 2.53 GAA. With Khabibulin gone after that season, he won back the starter’s job, playing in 48 games, winning 26 but registering a poor .895 save percentage. He would get his name on the Stanley Cup in 2010, but only as back-up to Antti Niemi. The Hawks buried him on a team in Switzerland the next season and he’s been there ever since.

(AP Photo/Paul Beaty)

8. Mark Messier – Vancouver Canucks 1997

The same year the Philadelphia Flyers gambled and lost on dynamic, but young, center Chris Gratton, the Canucks swung the other way and inked 36-year-old legend and pivot Mark Messier. Vancouver believed, to the tune of three years and 20 million smackers that Mess could lead them back to the promised land, along with former coach Iron Mike Keenan, who he won a Cup with in 1994 (playing against the Canucks). Right off the bat, the popular Messier became unpopular. First, he demanded his no. 11, even though it had been retired in honor of the early death of Wayne Maki (who passed unexpectedly in 1974). Then he went out and had the worst season, points-wise, in a full season with just 60 in 82 games. Age and injuries slowed him considerably and he wouldn’t push past the 60 mark in two more seasons, as well as being a double-digit minus each year.

(CP PHOTO/Chuck Stoody)

7. Sergei Samsonov – Montreal Canadiens 2006

Little guys sometimes get short shrift when it comes to respect and money, but Muscovite and height challenged winger Sergei Samsonov cashed in on both counts in 2006. For years a dynamic presence down the wing in Boston (376 points in 514 games), Samsonov rose to prominence after being acquired at the 2006 deadline by Edmonton. He had 16 points in 19 games there (after 37 in 55 for Boston), before helping the Oilers attack in an ill-fated run to the finals that year, recording another 15 points in 24 games. Edmonton couldn’t match the Montreal Canadiens offer to Samsonov in free agency that summer, a two-year, $7.05 million deal. Unfortunately, Samsonov became a huge disappointment, tallying just nine times and adding 17 assists in 63 games. The Habs waived him during that horrible season and later traded him to Chicago.

(CP PHOTO/Paul Chiasson) Canada

6. Wade Redden – New York Rangers 2008

The Rangers have made so many dubious deals over the years, they could have their own list of bad signings. Wade Redden’s play was so mediocre after signing with New York that they had to bury his contract in the AHL for two seasons before he could be rid of. Now, the Blueshirts could be forgiven for throwing a six-year, $39 million offer Redden’s way in 2008, as he was one of the best rearguards in the league for Ottawa 11 seasons running. However, there was the rumor of substance abuse issues regarding the former no. 2 overall pick, but GM Glen Sather ignored it. His first season on Broadway, Redden tallied his lowest point total since his sophomore season, a meager 26 points, along with an uncharacteristic -5 in 81 games. He followed that up with an even more tepid campaign, just 14 points in 75 games. Eventually, he was exiled to Hartford of the AHL, where he and his monster contract languished until 2012.

(AP Photo/Paul J. Bereswill)

5. Zigmund Palffy – Pittsburgh Penguins 2005

With the NHL coming out a season without hockey in 2004-05, there was optimism in Pittsburgh as the Penguins welcomed lottery pick Sidney Crosby to their club. Owner Mario Lemieux, looking to augment the phenom’s offence and jumpstart a moribund franchise, signed free agent and point-per-game man Palffy to a nice three year, $13.5 million contract. The former New York Islander and Los Angeles King stayed true to form in Pittsburgh, scoring 42 points in 42 games and was a responsible +5 for a team that wouldn’t make the playoffs that year. However, after game 42, Palffy surprisingly called it a career, allegedly due to a shoulder injury. His “retirement” didn’t last all that long though, as Ziggy returned to his hometown club team in Skalica in time for the 2007-08 season.

(AP Photo/Terry Gilliam)

4. Ville Leino – Buffalo Sabres 2011

One good season does not a star player make. Little wonder, too, that the Sabres have been such a bad team since signing flash-in-the-pan Ville Leino to an unwarranted six-year, $27 million pact in the summer of 2011. They made the playoffs that spring and haven’t been there since. The Finnish forward broke out with the Philadelphia Flyers in 2010-11, recording 53 points in 81 games, just after a superb 21 points in 19 playoff games with the team a year previous. He chipped in an additional five points in the 2011 playoffs as the Flyers went two rounds (beating Buffalo in the first one). Terry Pegula was way too desperate for scoring, then, when he tossed all that cash at Leino, who had all of 20 regular season points in 68 games before his breakthrough. He was an absolute dud in Buffalo thereafter, scoring just 10 goals (including zero in 58 games during the 2013-14 campaign) and 36 assists in 137 contests. He was a compliance buyout by the summer of 2014.

(AP Photo/Gary Wiepert)

3. Ilya Bryzgalov – Philadelphia Flyers 2011

There have been flaky goalies in the NHL and then there was Ilya Bryzgalov. The Philadelphia Flyers have had their fair share of goaltending woes over the last couple of decades, exacerbated by the fact they have thrown good money at suspect netminders. Bryzgalov was typical of the team’s myopia, inking him a whopping nine-year, $51 million contract. To clear the fiscal decks to accommodate the goofy puckstopper, the Flyers had to jettison Jeff Carter and Mike Richards in separate deals that summer. Once in a Flyers uniform, Bryzgalov’s play was as erratic as his pronouncements. After getting beat for nine goals in a 9-8 loss to Winnipeg early in the 2011-12 season, Bryzgalov said, “I have zero confidence in myself right now” and added he was “lost in the woods.” Hardly ringing self-endorsement for his new employer. His play was so up and down for two seasons that the Flyers used a compliance buyout in 2013 to rid themselves of the remaining seven years on the contract.

(AP Photo/Tom Mihalek)

2. Scott Gomez – New York Rangers 2007

Glen Sather only saved his bacon on the horrible contract he gave Scott Gomez in 2007 by convincing the Montreal Canadiens to trade for him in 2009. Slats, though, can’t be entirely forgiven for inking the two-time Stanley Cup champ to a whopping seven-year, $51.5 million deal. A reliable scorer with the Devils who was still just 27 when he signed with the Blueshirts, Gomez was to be counted on for good two-way play. In 2007-08, Gomez was right on point, piling up 16 goals and 54 assists in 81 games, followed by 11 points in 10 playoff games. However, his play slipped in New York the following season, a no-no for a high-priced athlete in the Big Apple. He slid 12 points to 58 and was a minus player (-2) for the first time in six seasons. Added to that was the fact the Rangers were ousted in the first round of the playoffs, with Gomez chipping in five points in seven games. After the trade that summer of 2009, his contract became an absolute albatross around the necks of Montreal management.

(AP Photo/Evan Vucci)

1. Jeff Finger – Toronto Maple Leafs 2008

Remember how we said this group was in no particular order? Well, that isn’t entirely true. If there is a poster boy for bad, bad free agent signings, long forgotten defenceman Jeff Finger would be him. The four-year, $14 million contract that he signed in 2008 will forever stain the usually astute Cliff Fletcher’s career resume. Trader Cliff and the rest of the Leafs’ brass chirped at length about Finger’s so-called shutdown ability, despite the fact he’d played just 94 games in the NHL with Colorado. He tallied 24 points and a +22 in an Avalanche jersey, while dishing out 121 hits and blocking 117 shots in his free agent year. In Toronto, though, he became yet another chapter in the sorry Leafs history of the time. In two seasons in blue and white, Finger played 105 games, recorded 33 points and was a -18. So much for being a “shutdown guy.” He and his fairly lucrative contract were sent to the Toronto Marlies, where he played until the 2011-12 season. He hasn’t been heard from since.

THE CANADIAN PRESS/Frank Gunn