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Down Goes Brown: Five players who never won a Cup thanks to bad timing

Let's look back at five players who had long and successful NHL careers that didn't include Stanley Cups, but who just missed being in the right place at the right time to win one.

You have to feel for NHL stars who never win a Stanley Cup. In most cases, their lack of a championship is hardly their fault. Hockey is a team game, and one player can only carry you so far. But that's probably little comfort to players who finish their career without ever skating a lap with the trophy. And that's especially true for the guys who just missed.

For example, Marcel Dionne is often mentioned as the greatest player to never win a Cup, and he may well be. But he also never came especially close. His team never made it out of the second round, and the three franchises he played for over his 18-year career – the Wings, Kings and Rangers – never won any Cups at all over that span.

Other players have come close in a given year. Gilbert Perrault helped get the Sabres to the final in 1975, and Roberto Luongo was one win away from a ring in 2011 with the Canucks. Brian Propp may have had the toughest luck of anyone -- he went to the Cup final on five separate occasions, but had the misfortune of running into an Islanders, Oilers or Penguins dynasty each time.

But then there's the group of star players who came close in a very different way: the guys who just had bad timing. They were great players, and they played for great teams. But they managed to be just a little too early or a little too late to be part of a Cup team, and ended up retiring without a ring despite most of their teammates getting one.

So today, let's look back at five players who had long and successful NHL careers that didn't include Stanley Cups, but who just missed being in the right place at the right time to win one.

Mike Gartner

Gartner hadn't come especially close to a Cup over the first decade-plus of his career with the Capitals, North Stars or Rangers. But in 1994, he finally found himself on a Cup favorite. By March, the Rangers were on their way to their second Presidents' Trophy in three years. With Mark Messier leading the way, Brian Leetch on the blueline and Mike Keenan behind the bench, the Rangers seemed set to finally break the franchise's 54-year Cup drought.

And as it turns out, they did. But Gartner didn't get to be a part of it. In yet another deadline deal, the 33-year-old veteran was sent to the Maple Leafs in exchange for Glenn Anderson.

Gartner and the Leafs nearly made it to the final themselves, before falling to the Canucks in the Western final. Meanwhile, the Rangers went on to win it all at Madison Square Garden (despite not getting all that much production out of Anderson along the way).

For Anderson, it was his sixth Cup ring. Gartner played until 1998, but never made it out of the first round again. He retired without a championship; in hindsight, he may have only missed by a few months.

Dino Ciccarelli

You could hardly say that Ciccarelli didn't come through in the playoffs. In fact, he began his career with the greatest rookie playoff performance the league had ever seen, scoring 14 goals for the North Stars while helping them to an unlikely appearance in the 1981 final. They lost to the powerhouse Islanders in five games, but Ciccarelli's rookie record still stands to this day.

It was another decade before Ciccarelli got to play for another legitimate contender, as he toiled for the North Stars and Capitals (after being traded for Gartner). But during the 1992 offseason, he was dealt to a Red Wings team that seemed headed toward big things. After back-to-back seasons in which the team racked up 100-point seasons only to bow out in the opening round, Ciccarelli and the Wings finally broke through with a trip to the Cup final in 1995. But they bowed out to the Devils in four straight that year, then capped off a dominant 131-point season with a disappointing second-round loss to the Avalanche in 1996.

By the 1996 offseason, Ciccarelli was 36 years old and 12th all-time in NHL goal scoring. He seemed like the kind of veteran presence the Red Wings would need to finally get over the hump. But facing a roster crunch and fearing they could lose him in the waiver draft, the Red Wings chose to trade Ciccarelli to the Lightning for a draft pick.

The feisty winger had something left in the tank, scoring 35 goals for the Lightning over the 1996-97 season. But the team missed the postseason, and Ciccarelli had to watch his former Red Wings teammates win the first of back-to-back Cups without him. He played until 1999, but never made the playoffs again after leaving Detroit.

Ryan Smyth

There aren't many better hockey stories than the beloved star player who returns home. If the player is the one who makes it happen, all the better. And if the story involves mending a relationship, well, who wouldn't want to see that?

So it's hard to get too negative over the 2011 offseason trade that saw Smyth go from the Kings to the Oilers. He'd made a stunning departure from Edmonton at the 2007 trade deadline; he seemed to be on the verge of signing an extension with the only NHL team he'd ever known when word came down that he'd been dealt to the Islanders instead. A few months on Long Island were followed by two years in Colorado and two more in Los Angeles. Now, the 35-year-old veteran wanted to come home.

And so, on June 26, 2011, the Kings agreed to Smyth's request for a trade back to Edmonton. The deal capped off days of speculation, and Smyth was greeted with open arms by Oilers fans. Captain Canada had returned, and he wasn't done – he played for three more seasons, showing occasional flashes of the skill and grit that had made him one of the most popular players in franchise history. It was all just about perfect.

Well, almost. There was that one nagging detail: the Oilers were terrible. This was right in the middle of that awful era in which Edmonton couldn't win anything other than draft lotteries, and they missed the playoffs in each year of Smyth's return. Meanwhile, the Kings went on to win the Stanley Cup twice in that time, including the very next season after Smyth asked to be dealt away.

Would the longtime Oiler want a do-over? Maybe not – there are bigger things in life than winning a Cup, after all. But purely in terms of championship odds, moving from the 2011-12 Kings to the Oilers was probably about as bad as it gets.

Bernie Nicholls

Best known for his ridiculous 70-goal season in 1988-89, Nicholls actually found himself leaving a team on the verge of a Cup twice. Most fans probably remember that he went from the Rangers to the Oilers as the key piece in the Messier trade in 1991. That's really not all that much of a near-miss; not only did it come nearly three years before New York's title win, but the Rangers almost certainly don't claim the Cup if Messier doesn't arrive to lead the way.

But what's sometimes forgotten is that Nicholls nearly managed to stop his old team from getting that 1994 Cup. He was playing for New Jersey that year, and was a factor in the legendary conference final showdown between the Devils and Rangers. In fact, Nicholls scored two goals in the 4-1 win that put the Devils up 3-2 in the series, forcing the Rangers to the brink of elimination and spurring Messier's famous Game 6 guarantee.

Stephane Matteau's Game 7 overtime goal broke hearts in New Jersey, but the good news was that the Devils turned out to be just a year away from a championship of their own. But Nicholls didn't get to be a part of it; he headed to Chicago as a free agent that summer. That was a pretty good fit; Nicholls led the Blackhawks in scoring and the team made the conference final before losing to Ciccarelli and the Red Wings. The shifty center played until 1999, but didn't make it out of the second round again.

Pat Lafontaine.Image by: Getty Images

Pat Lafontaine

We've covered four guys who left just before their team won the Cup. Let's finish off with a Hall of Famer who was on the other side of the equation.

When LaFontaine arrived on the scene with the Islanders in 1983, it seemed almost unfair. The team was already a dynasty, having won four straight Stanley Cups while icing a roster packed with superstars. Now, thanks to a 1981 trade with the Colorado Rockies, they also had the third overall pick in the draft, which they used on the ridiculously talented LaFontaine.

And while he didn't have much impact in 1983-84, LaFontaine did indeed go on to develop into one of the league's top offensive threats. Unfortunately for him, the Islanders' Cup years were already over by the time he walked in the door. They made it back to the Cup final for a fifth straight year in 1984, but lost to the up-and-coming Oilers. It was a passing of the torch, with Edmonton winning five of the next seven titles while the Islanders didn't get past the second round again until 1993.

By then, LaFontaine was in Buffalo (and racking up a career-best 148-point season). His career ended early due to concussions in 1998, and he went down in history as one of the best to never win it all. You can hardly blame him for that. But you have to wonder if he sometimes felt like the guy who showed up late to a legendary party, only to find out it had already ended.

Sean McIndoe has been writing about the NHL since 2008; you may know him from Twitter as @downgoesbrown. His e-book, The 100 Greatest Players in NHL History, is available now. He appears weekly on


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