Signing free agents can be a crapshoot at the best of times.

Usually, the back lot at the annual NHL free agent auto sale in July is full of late model jalopies. Some are still running in good order, while others turn out to be lemons.

In the past 20 years or so, the free agent frenzy dominates the summer headlines, with teams forking over king’s ransoms to get their hands on what they believe are game-changers.

Once in a while an in-his-prime player is made available, but that isn’t the norm. For that reason, we think John Tavares won’t make it to free agency in 2018, as the Islanders would be foolish not to extend him. The Oilers made sure Connor McDavid won’t be up for auction anytime soon, inking him to a lavish deal this summer.

All that aside, there have been some very astute signings — of the under-the-radar or surprising type — that have helped teams gather steam and in a lot of cases, win Stanley Cups because of the contributions of those free agents.

Here are the 15 best, and under-rated signings in NHL history, in no particular order.

15. Charlie Huddy – Edmonton Oilers 1980

On just about every dynastic hockey club, there are those “glue” guys who contribute in small, but significant ways to the team’s overall success. Defenceman Charlie Huddy was one of those guys for the powerful Edmonton Oilers of the 1980s. The Oshawa native went undrafted after putting in two pretty good seasons with the hometown Generals of the OHL in the late 1970s. The Oilers took a chance on him in 1980, signing him to a contract to join Wayne Gretzky et al in Edmonton. Huddy was a jack-of-all-trades on the Edmonton blue line for over a decade, tallying 368 points in 694 regular season games, and 77 points in 138 playoff games. He was also a collective +251 in his career, winning the plus-minus award in 1982-83 with a +62. Huddy was also one of seven Oilers to be on the franchise’s five Stanley Cup winning teams.


14. Brad Richards – Chicago Blackhawks 2014

By the summer of 2014, former Stanley Cup winner Brad Richards was considered over-the-hill and only to be signed as a complementary piece to a new team. The two-time All-Star and Conn Smythe winner for the 2004 champion Tampa Bay Lightning wasn’t exactly involved in a bidding war for his services. The Chicago Blackhawks, who turned their roster over significantly after winning titles in 2010 and 2013 and were coming off a loss in the Western Conference finals in 2014. Richards was signed to a cap friendly one-year, $2 million deal after scoring 51 points in 82 games for the New York Rangers in 2013-14. He had a pretty fair season in a third line role, notching 37 points and winning 48.4 percent of his face-offs. Come the playoffs, the man with 90 points in 118 previous post-season contests contributed nicely to Chicago’s third Cup in six springs, scoring three goals and 11 assists in 23 games.

(AP Photo/Nam Y. Huh)

13. Joe Nieuwendyk – Dallas Stars 1995

Joe Nieuwendyk was in his prime in 1995 when he spurned the Calgary Flames offer of a three-year, $6 million offer while trying to negotiate a long-term deal. In his case he wasn’t a “true” free agent, as held out until December 1995 and was traded to Dallas for then unknown Jarome Iginla. However, the Stars didn’t hesitate to sign him to a new contract worth $11.3 million over five years. The two-time 50-goal scorer and 1988 Calder Trophy winner had a Stanley Cup ring on his resume, but his production had slid from the early halcyon days. However, by the 1997-98 season, a 31-year-old Nieuwendyk fired 39 goals (his highest total since 1990-91) and then helped lead the Stars to the Western Conference finals. In 1998-99 he registered 55 points in 67 games for the resurgent Stars and saved his best for last. He had his best post-season ever, scoring 11 goals and 10 assists in 23 games, winning the Conn Smythe trophy for the first-time champion Stars.

(CP PHOTO/Chuck Stoody)

12. Marian Hossa – Detroit Red Wings 2008

For many seasons, Marian Hossa was a good player on some decent but not great teams. He reached a high of 100 points for the Atlanta Thrashers in 2006-07, but found limited success in the playoffs with them or with the Ottawa Senators teams he toiled with earlier. In 2008, after being acquired by Pittsburgh at the trade deadline, he finally was able to showcase his considerable skill, scoring 26 points in 20 playoff games as the Penguins reached the finals, only to lose to Detroit. Hungry for a title and nearing 30, Hossa opted to sign with the Red Wings, turning his nose up at a five-year, $35 million contract from Pittsburgh to ink a one-year, $7.45 million pact in the Motor City. It turned out to be an interesting move, as he could be a great second line option in Detroit, instead of counted on to play big minutes in Pittsburgh. He scored 40 goals that year for the third and last time in his lengthy career and followed it up with 15 points in 23 playoff games, getting the Wings within a whisper of a title repeat against his old team, the Penguins. He would later be a great pick-up and win multiple Stanley Cups in Chicago.

(AP Photo/Paul Sancya)

11. Ron Francis – Carolina Hurricanes 1998

The lure of playing for the franchise that drafted him fourth overall in 1981 was too much for Francis not to consider in the summer of 1998. The veteran forward was the face of the Hartford Whalers franchise for nearly 10 seasons when he was included in a blockbuster deal to go to the eventual champion Pittsburgh Penguins in the spring of 1991. Ronnie Franchise would win two straight Stanley Cups with the Pens, scoring 44 points in 45 games over two post-seasons. The great two-way player and centerman remained with Pittsburgh until 1998 and opted to re-join his original team, freshly moved to Carolina. Well into his 30s, Francis put in yeoman’s work with the ‘Canes, winning a Lady Byng and Clancy trophy in 2002 after scoring 77 points in 80 games (at the age of 38). He was also instrumental in instilling a winning tradition in Carolina, helping take the team to its first Stanley Cup final and registering 16 points in 23 games.


10. Luc Robitaille – Detroit Red Wings 2001

Lucky Luc Robitaille was enjoying a career renaissance with the Los Angeles Kings in the late 90s/early 00s, when he decided to gamble on a shorter term deal worth less money to join the Red Wings in free agency. The Wings gave him $9 million over two years and he was coming off three straight seasons of 30+ goals for the Kings. Having never won a championship, taking less money and term was his saving grace. Robitaille scored 30 goals for the fourth straight year (and last time in his Hall of Fame career) on a deep, deep team. At 36, he wasn’t as nimble as he was earlier in his career, so Robitaille didn’t get as much ice time in the post-season, but he still managed to fire four goals and add five assists in 23 games (13:16 average ice time).

(AP Photo/Jack Dempsey)

9. Bryan Trottier – Pittsburgh Penguins 1990

By the time the summer of 1990 rolled around, former four-time champion, league MVP, Smythe Trophy winner and NHL scoring champion Bryan Trottier was a shadow of his former robust self. His two-way play was still appreciated on Long Island, but his scoring prowess had all but left him, as he posted a career low 24 points in 59 games for the Isles in 1989-90. The Islanders, wanting to get younger up the middle, released Trottier from his contract, making him a free agent. He signed with Pittsburgh, which could use his leadership and strong defensive play. Trottier would play a vital role on a Mario Lemieux led team hungry for a championship. He was a strong checking center and penalty killer for Pittsburgh and was rewarded with two more Stanley Cup rings in 1991 and 1992.

(AP Photo/John Swart)

8. Brian Rafalski – Detroit Red Wings 2007

Rafalski flew so far under the radar that after four decent seasons with the University of Wisconsin, the undrafted defenceman had to travel to Sweden in 1995 to play pro hockey. He shifted to the Finnish league and put up 53 points in 54 games with HIFK Helsinki in 1998-99, catching the eye of New Jersey Devils scouts in the process. Already 26 in May of 1999, he signed with the Devils and was a key piece to two championship teams in Jersey (2000 and 2003). Rafalski had his best season with New Jersey in 2006-07 (55 points) and in free agency after the season was deemed too expensive. Yet, Detroit had faith the 33-year-old rearguard still had lots left, signing him to a five-year $30 million deal. With the Wings, Rafalski was second banana to Nicklas Lidstrom, like he was to Scott Niedermayer and Scott Stevens in Jersey. But, he was instrumental in Detroit’s 2008 Stanley Cup run, registering 14 points in 22 games.

(AP Photo/Gene J. Puskar)

7. Martin St. Louis – Tampa Bay Lightning 2000

Like Brian Rafalski above, tiny forward Martin St. Louis got no love from the NHL despite scoring nearly two points per game in four seasons with the University of Vermont. He found no takers as a free agent and toiled in the minors for parts of two seasons before the Calgary Flames brought him up in early 1999. Ice was in short supply for St. Louis and after 69 games in Calgary, he was left unprotected in the 2000 expansion draft, where he was again passed over. Tampa Bay took a flier on him and the rest is history. By the 2003-04 season, he was the NHL’s leading scorer, winning the Hart and Pearson trophies as well. St. Louis was pivotal to the Lightning’s first and only championship, too, scoring nine goals and a post-season high 15 assists in 23 games. In all, he would be named to four second All-Star teams, a First All-Star team, win three Lady Byng’s and another Ross Trophy as leading scorer.

(CP PHOTO/Frank Gunn)

6. Chris Osgood – Detroit Red Wings 2005

When the names of the top goaltenders ever to play in the NHL are argued, seldom does Chris Osgood’s name pop up. Rather, it would be his former teammate, Dominik Hasek and a host of other netminders. But, all Osgood did was win in his two tenures with the Red Wings. Drafted 54th overall in 1991, he wold play eight seasons with Detroit initially, winning Stanley Cups in 1997 and 1998 (as a starter, going 16-6), before spending three seasons elsewhere after 2001. In 2005, the Wings brought a more seasoned Osgood back, signing him to a very cheap two year, $800,000 contract. In 2007-08 he platooned with Hasek and won a Jennings Trophy, logging a career best 2.09 goals against average (also NHL best) in 43 games. The 35-year-old veteran then usurped starting duties in the 2008 playoffs, winning 14 and losing four and recording three shutouts to backstop the Red Wings to another title.

(AP Photo/Carlos Osorio)

5. Petr Sykora – Pittsburgh Penguins 2007

For many years, Plzen, Czech Republic born Petr Sykora was a steady point producer for the New Jersey Devils after being drafted by them in the first round (18th overall) in 1995. A great playmaker who was also astute defensively, Sykora piled up 394 points and a +91 in 527 games with New Jersey, winning a Stanley Cup with them in 2000. He would bounce around after that, helping the Mighty Ducks of Anaheim to a finals appearance in 2003 and then having stints in New York and Edmonton, before signing as a veteran UFA with Pittsburgh in 2007. He scored 63 points in 81 games for Pittsburgh during the 2007-08 season and had a good playoff run, firing six goals and three assists as the Pens went to the finals. Injuries would crop up on him during the 2008-09 campaign, where he tallied 46 points in 76 games. While he didn’t play much in the post-season due to a shoulder injury (just seven games), Sykora did get his name on a second and last Stanley Cup.

The Canadian Press/Frank Gunn

4. Teemu Selanne – Anaheim Ducks 2005

The Finnish Flash set the hockey world on its ear by scoring a rookie record 76 goals in 1992-93 with Winnipeg. It would take him a few more seasons to crack the 50-goal barrier again, with 51 in 1996-97 and a league best 52 in 1997-98, both times with Anaheim. The popular Finn, who will be inducted into the Hall of Fame this year (coincidentally with former teammate Paul Kariya), found much personal success in his first 12 seasons (including stops in San Jose and Colorado) but played little in the post-season. That all changed with a return to the Ducks in 2005 at the age of 35. Dogged by recurring knee problems, Selanne recorded just 32 points with Colorado in 2003-04, and seemingly washed up he got just a one-year, $1 million contract to return to Anaheim in 2005 after the lockout year. He didn’t disappoint his owners in 2005-06, scoring 40 goals and 90 points, followed by 14 points in 16 playoff games. Selanne upped the ante in 2006-07, scoring 48 times and assisting on 46 others in all 82 games. He was critical to the Ducks fortunes in the 2007 playoffs, registering 15 points as Anaheim won a championship.

(AP Photo/Mark J. Terrill, File)

3. Adam Graves – New York Rangers 1991

Adam Graves was strictly a spare part during his days with the Detroit Red Wings, who drafted him 22nd overall in 1986. A lopsided trade in November 1989 to Edmonton changed his career. He didn’t pile up massive numbers with the Mark Messier led Oilers, but did win a Stanley Cup with them in 1990, scoring 11 points in 22 games. He spent just one more season in Edmonton before free agency beckoned in 1991. He signed with the Rangers and was reunited with Messier and Jeff Beukeboom. Graves point production steadily crept up for the Blueshirts, from 59 points in 1991-92 to 65 in 1992-93, but that team didn’t make the playoffs. In 1993-94, Graves broke out in a big way, scoring a career high 52 goals, then a franchise record. Graves would top it off by firing 10 more in 23 playoff games to help the Rangers win their first Stanley Cup in 54 years.

(AP Photo/Bill Kostroun)

2. Sergei Gonchar – Pittsburgh Penguins 2005

Until signing with Pittsburgh in 2005, Sergei Gonchar toiled in relative anonymity with the Washington Capitals for 10 seasons and then 15 games with the Boston Bruins late in the 2003-04 campaign. A great puckmover and powerplay point specialist, Gonchar tallied 416 points in 654 games with the Capitals, but played in only 51 playoff games, followed by seven in Boston. So, at age 31 in 2005, Gonchar put his signature to a five-year, $25 million contract to play in Pittsburgh. It would prove to be a transformation point, as the talented Russian defender gave the Penguins the kind of play from the backend they hadn’t had since Paul Coffey called the Igloo home. The young Penguins had Sidney Crosby in the line-up, too, but failed to make the post-season in 2005-06. For his part, Gonchar scored 58 points that season, followed by a career high 67 points in 2006-07. His personal post-season breakthrough came after playing just 25 games in 2008-09 (19 points). He scored three goals and 11 assists in 22 games as Pittsburgh hoisted the famed chalice for the first time in 17 years.

(AP Photo/Gene J. Puskar)

1. Arturs Irbe – Carolina Hurricanes

There isn’t much call for diminutive goaltenders in today’s NHL. Six feet is considered short, so guys like 5’8″ Latvian netminder Arturs Irbe wouldn’t get a second look. Despite his small stature, Irbe was drafted 196th overall by Minnesota in 1989. He debuted with the San Jose Sharks during the 1991-92 season and for the first seven seasons was a journeyman, also putting in stints with Dallas and Vancouver. In 1998, Irbe signed with Carolina and everything clicked. He would play 75 games with the Hurricanes in 1999-00 and a career high 77 in 2000-01. In six years with the ‘Canes, Irbe would post 20 of his 33 career shutouts, as well as 130 of 218 lifetime wins. His most important contribution was backstopping the Hurricanes to their first Stanley Cup final in 2002. He went 10-8 in 18 games, with a sterling 1.67 goals against average and .938 save percentage.

(CP PHOTO/Frank Gunn)