The Greatest

Greatest NHL signings that almost happened

10 greatest NHL signings that almost happened, but didn’t Wayne Gretzky 10 greatest Stanley Cup playoff series of the 1990s 10 greatest NHL conference finals of all time
The Great One caused Leafs Nation great agony in the 1993 postseason. He did it again a few years later in the offseason. (Photo by Graig Abel/Getty Images)

In a rocking requiem for their home-state Hartford Whalers, The Zambonis lamented the moves of other NHL teams. Appropriately, one line mentions “Quebec’s Nordiques and the Golden Seals” in succession.

Both of those bygone brands have a key common thread. They had a chance to sign a No. 1 overall draft pick, but let him get away. Within another decade, they were in another time zone or defunct altogether.

High-profile unfinished NHL signings include ones of almost every player who contends for the greatest-of-all-time title. Those legends may have influenced championship runs and dynasties, or a lack thereof. Less debatably, they denied a fan base sentimental value by spurning a team’s offer.

In others cases, a restricted free agent inked an offer sheet, only to have his previous employer match it. As a result, the external transaction was as good as fantasy.

Based on a combination of a player’s legend, the affected franchises’ fortunes and marketing implications, the following potential-but-vetoed NHL signings are the most momentous in league history. All statistics and award information are according to the Internet Hockey Database.

10. Sergei Fedorov to Carolina
In the pre-salary cap era, matching an offer sheet was easier for more privileged teams. So when their two-way speedster held out for the first five months of 1997-98 before fielding an offer from the Hurricanes, the Detroit Red Wings took action.

Upon negating the pact, Detroit started suiting Fedorov up again, and soon repeated as Stanley Cup champions. The franchise won its next Cup four years later by vanquishing none other than Carolina in five games.

In 2015, Hurricanes owner Peter Karmanos reminisced on the deal and series with Yahoo!’s Greg Wyshinski. He recalled how the teams had split the 2002 final’s first two games in Detroit. Back home, the Hurricanes almost regained the upper hand, but fell in triple-overtime after Fedorov helped avert a regulation loss.

“First of all, if we had won that game, it really would have put the pressure on the Red Wings,” Karmanos told Wyshinski. “Had they not matched (the offer sheet), we would have won another Cup.” Namely, another one four years before Carolina’s only title to date in 2006.

9. Eric Lindros to Quebec
The year after going first overall at the 1991 NHL Draft, Lindros withheld his ink from the Nordiques. Multi-year deals ranging between $50 million and $55 million were reported, but never signed.

By the next draft, Quebec relented and swapped Lindros’s rights to the Philadelphia Flyers. Without their prized pick, who openly slighted the French-Canadian community, the Nordiques ultimately transferred to Denver.

As it happened, Lindros was at his peak concomitant with the Nordique faithful’s nadir. He won the 1995 Hart Trophy, and helped the Flyers to their first of three conference finals in six years.

Of course, pointing to Peter Forsberg, many conclude that the other party won the deal long-term. But that was only after the Nordiques morphed into the Colorado Avalanche. Historians are thus left to imagine what could have been for Quebec if the more readily marketable Lindros signed there.

8. Joe Sakic to NY Rangers
Ranger detractors, especially Islanders and Devils fans, love to remind their rivals of the Stanley Cup scoreboard since 1940. The elder franchise has mustered one title (in 1994) in the past 78 years. Meanwhile, the crosstown rival established in 1972 has won four in that span. More recently, the cross-Hudson River foes who came in 1982 have taken three.

But maybe a winning leader like Sakic could have helped the Blueshirts sustain their power longer. While the team that unsuccessfully pursued him ended his (and the NHL’s) Quebec era in 1995, he has had the more recent triumphs. With Colorado, he accepted the 1996 Conn Smythe Trophy and Stanley Cup from Gary Bettman.

That would end the first of six deep playoff runs in seven years for Sakic’s Avs. Four culminated in close conference-final losses, while the other ended in another title in 2001. The captain was that year’s regular-season MVP as well.

In between, Colorado secured his continued services by matching the Rangers’ offer sheet in 1997. Had New York won that footrace, Sakic could have filled the Vancouver-bound Mark Messier’s void and joined Wayne Gretzky for The Great One’s final two seasons.

7. Ray Bourque to Los Angeles
Together with fellow future Hall-of-Fame defenseman Rob Blake, Bourque was a key piece in Colorado’s 2001 Cup run, tangibly and intangibly. But if not for one draft-day deal, the two might have gone to a previous final together.

The Boston Bruins signed Bourque after obtaining him with the eighth overall pick in 1979. Had they held back, the future five-time Norris Trophy winner would have been wide open for the Kings.

By 1993, Bourque was one year away from his fifth Norris in eight seasons. He was also saturating the scoresheets with more than a point per game. Meanwhile, L.A. was at its own peak, entering its first Stanley Cup Final, though it lost in five games to Montreal.

Would Bourque have made the difference as the blue-line anchor behind an offensive leader named Gretzky? If nothing else, he would have made that series more competitive. Instead, he and Blake would famously defeat L.A. in their only actual playoff encounter.

6. Guy Lafleur to California
In the NHL Draft’s formative years, Montreal fans had to adjust to not automatically seeing Quebecois-born prodigies stay home. And as 1971’s reigning champions, the Habs could only access provincial hero Guy Lafleur via trade.

Lo and behold, the California Golden Seals made it happen by sacrificing their right to the first pick. In a blockbuster deal, the most prominent piece went to the established hockey market.

Fellow rookie Joey Johnston would join the Seals that year, and tallied 185 points in four seasons. That was good for California’s all-time lead, as the team would move to Cleveland in 1976.

Back in Quebec, Lafleur amassed 163 points between 1971-72 and 1974-75. He started sizzling after that, leading the Habs to four consecutive Cups to close the decade.

Oh, what could have been for Bay Area hockey if Lafleur formed a dynamic duo with Johnston?

5. Gordie Howe to NY Rangers
Remember when your crush said they weren’t ready for a relationship, then started dating someone else soon after? The Rangers felt that sort of pain upon failing to secure Howe’s rights after his first amateur training camp. He later joined the Red Wings when he turned NHL age, and stayed until 1971.

New York’s 54-year championship hex enveloped all of Howe’s off-and-on playing career. Their closest whiff during that time came in 1950, when they lost Game 7 to Detroit in double-overtime.

Incidentally, Howe missed that series after sustaining a scary head injury in the preceding round. But under different circumstances, he could have been healthy and sporting a Blueshirts sweater. A player of that magnitude would have had that rare ability to make all the difference.

Besides breaking up a drought, Howe could have had a greater media impact in New York. His time there would have overlapped with those of Yankee greats Joe Dimaggio, Mickey Mantle and Roger Maris. Fans who leaned National League had Jackie Robinson of the Dodgers and Willie Mays of the Giants for a time. The Mets eventually replaced those NL tenants in 1962.

Imagine the unifying force Howe could have been in baseball’s offseason, when the Rangers were the only local hockey ticket.

T-3. Bobby Orr to Montreal or Toronto
When the Canadiens and Maple Leafs still had de facto territorial rights to local prospects, Orr’s region was fair game for all of the Original Six. But the pride of Parry Sound could have stayed in Canada, if not in Ontario.

As Orr noted in his autobiography, the two Great White Northern franchises took notice. But neither team was too eager to pursue him when he was barely an adolescent.

With that loose puck, the NHL’s longest-running U.S.-based team pounced. Orr would subsequently go to Boston at the earliest possible age. He spent the next decade fully reinvigorating the Bruins and reinventing the blueliner’s job description.

As it happened, by winning two Cups with Orr, the B’s were the only team keeping Montreal from claiming six in a row. The Habs won four in six seasons right after losing the final to Toronto in 1967, Orr’s rookie year.

The Maple Leafs have infamously failed to reach another Cup final since that title. But what if they had the foresight to put Orr was on their side for 10 years?

T-1. Wayne Gretzky to Vancouver or Toronto
Orr or not, the Leafs did start a half-century (and counting) of futility after 1967. Another otherworldly Ontarian is considered responsible for one of Toronto’s most agonizing letdowns.

Between a non-call for high-sticking Doug Gilmour and clinching goal in Game 6, then a hat trick in Game 7, Gretzky catalyzed the 1993 Campbell Conference final’s dramatic twist ending. With that, the Kings made their aforementioned first appearance in the championship round.

Three years later, as a free agent coming off a stint in St. Louis, the Brantford boy had a chance to join his nearest childhood team. But the Rangers won out, and rostered Gretzky for his final three seasons.

Incidentally, whereas New York missed the 1999 playoffs, Toronto reached its next conference final the month after Gretzky retired. Could he have made a difference and at least made the Buds replace Buffalo as the Dallas Stars juggernaut’s last victim?

Mortal hockey fans will never know. Likewise, Western Canadian fans will never know how the Canucks and The Great One might have fared together. The man who started with the rival Oilers nixed an offer from Vancouver as part of his 1996 summer search.

After they failed to sign No. 99, the Canucks failed to make the 1997 playoffs by a mere four points. But even without a winning finish, odds are Canadians at large would have loved to see their involuntary gift to the U.S. return north before he retired.

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