Simpson: No Oilers Cup as special as 1988

Mark Messier (left) and Wayne Gretzky celebrate their last Stanley Cup together in 1988. (AP/Rusty Kennedy)

On May 26, 1988, 25 years ago this weekend, the Edmonton Oilers won the Stanley Cup. It was their fourth Cup in five years. They would win another in 1990. But, to me, nothing was quite as special as that ’88 Cup win.

It was the fourth and final Stanley Cup Wayne Gretzky would win in his Hall of Fame career. It was the first of two Cups my brother Craig would win in his 10-year NHL career — and, because of that, I had a front row seat. It also marked the renewal of a hockey tradition that continues to this day.

For Craig, that season began in Pittsburgh. After being chosen by the Penguins as their first pick in the 1985 draft (second overall to the Leafs’ pick of Wendel Clark), Craig was just beginning to establish himself as an NHL player when, on Nov. 24, 1987, he was traded to the Edmonton Oilers as part of a package for Paul Coffey.

The shock of being traded was quickly replaced with awe when Craig found himself playing left wing on a line with Mark Messier and Glenn Anderson. Pretty heady stuff for a 20-year-old. He learned that the expectations of this band of brothers were quite different from that of the Penguins in those days. Anything less than a Cup was unacceptable in Oil country. And while the Calgary Flames finished the 1987-88 regular season as the Presidents’ Trophy winners, Wayne Gretzky would say this was the best Oilers team ever assembled.

The Oilers would beat the Winnipeg Jets handily four games to one in the first round of the playoffs before facing the rival Flames in Round 2. When Gretzky’s slapshot beat Mike Vernon in overtime of Game 2 – shorthanded no less – the series was effectively over as the Oilers won the next two for the sweep. The Oilers would later say that once they had beaten the Flames, they knew they had the Cup won.

Next they beat the Detroit Red Wings in five games, setting up a Stanley Cup final between Edmonton and the Boston Bruins.

The Oilers won both games at home before the series swung to Boston. After winning Game 3 at the old Boston Garden, my parents, brother and I flew to Boston for Game 4 in hopes of witnessing a sweep and Craig’s first chance to sip from the Stanley Cup. Seated in the row behind Walter and Phyllis Gretzky, along with Wayne’s then-fiancée, Janet Jones, I remember the excitement in the air was almost as thick as the fog. Old barns like this weren’t exactly built for hockey in late May.

And then it happened.

Craig had scored with 3:23 left in the second period to tie the game 3-3. But just as the team began to celebrate, a power failure plunged the arena into darkness. The fans as well as the players were stunned, not quite sure what to do next. After a few moments of darkness, the players retreated off the ice and we decided to follow the Gretzkys down to the Oilers dressing room. In the dark glow of the emergency lighting, we waited and wondered. Were the lights coming back on? Would the game resume? The players started coming out of the dressing room stripped of their jerseys and skates but still in their equipment, waiting for NHL president John Ziegler to announce what would happen next.

But the Stanley Cup party for the Edmonton contingent, arranged at a local Boston hotel by Oilers scout, the late Ace Bailey, would have to wait as Ziegler finally determined that, with no chance of the lights coming back on, Game 4 would be suspended. Disappointed, we flew to Edmonton for the replay of Game 4, where the Oilers would finally “sweep” the Bruins.

We all watch the Stanley Cup celebration on TV each spring. We have come to expect the brutal beauty of watching bearded, battle weary men, exhausted and exhilarated, kissing a giant hunk of metal while using their last bit of strength to raise it over their heads. I’ve since been witness to this annual rite of spring numerous times as a member of the media covering the Cup final. But there’s nothing quite like the feeling of watching a family member, someone you’ve watched work for this moment their entire lives, finally see that dream come true.

And then something else happened.

The other special part of the 1988 Stanley Cup celebration was what Wayne Gretzky did next. In the midst of the euphoria, he grabbed the Cup and took it to centre ice. He plopped it down on the ice and started yelling at his teammates to come gather around it. Then to the coaches, management, trainers, equipment staff, scouts. And there they all were, in the organized chaos of a frat house keg party, Wayne Gretzky wanted to make sure everyone involved with the team that year was part of a photo that is now as much of the tradition of winning the Stanley Cup as sipping champagne from it is (which, I can tell you, has never tasted so sweet).

Twenty-five years have passed since that night. In interviewing Wayne for this feature I had assumed that Oilers team had started the tradition of the group photo, but was told by him that wasn’t so. Wayne said he had seen photos from the ’50s and ’60s Cup championship teams who had done it before. He wanted to renew a tradition that had been lost.

He said he had no idea then that it would be his last game as an Edmonton Oiler, let alone his last Stanley Cup. But what a fitting way to capture a special moment, frozen in time.

Watch behind the scenes footage from the 1988 Stanley Cup celebration inside the Oilers dressing room.

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