If only we could find a modern-day Bert Olmstead to help get the Leafs over the top….

In recent days (well for longer than that, really) we’ve chatted here at VLM about what the Leafs need to get to that next “level”—you know, where they become a team that is a legitimate contender to win their Conference year after year.

Most of us agree that there are pieces in place, some pretty good pieces at that.  There is a sprinkling of young players already on the roster—or in the pipeline that will be here soon, as well.  But how close are we, really, to contending?

A few of us have opined here that the Leafs are maybe three or four key pieces from being in the rarified air of those legitimate annual contenders.  Of course that ‘number’ (of necessary pieces) can change with defections, injuries and poor performance, or on the positive side of the ledger, through the sudden emergence of young players or other unforeseen circumstances.

Regardless, most of us would agree that the Leafs aren’t there quite yet, despite the hopeful moments they gave us in that dramatic series with the heavily-favoured Bruins earlier in May.  A few people have commented in this space that they would like to see the Leafs acquire or find (somehow) a player with skill and toughness, someone who could score, make plays, fight for the puck and also drop the gloves if required.  We’ve had guys like that in the past, including Gary Roberts during the Pat Quinn era. Roberts brought a lot to the Leaf lineup, no question.

But because old memories are sometimes the best memories, on this kind of subject, I often harken back to a player of my youth, a time when I was just beginning to understand, appreciate and fall in love with hockey.  That was the late 1950s, which just happens to be a time when Punch Imlach arrived on the scene in Toronto and cobbled a team together.  It was a Leaf squad (some were castaways from other organizations, others made the jump from the Leaf-sponsored junior ranks) that had some elite young players along with a few tough two-way performers.  He also made sure the squad had a huge dose of experience and playoff savvy. 

That team became, in the 1960s, a four-time Stanley Cup champion.  And one of the players who helped the Leafs get to that championship level was a hard-edged winger by the name of Bert Olmstead (shown at right with the Habs in the early to mid 1950s).

I've written about the former Hab here before but a bit of background always helps.  In those golden days of hockey, the NHL was comprised, of course, of only six teams.  Don’t be fooled, however.  The competition was fierce, and while there were virtually no Americans in the league and no imports from Europe, Canadian players from across the country fought to earn one of the maybe 100-120 or so (17-18 players to a team in those days, I seem to recall) regular jobs available in the league.

It wasn’t any easier back then for aspiring players.

For his part, Olmstead had played on several Cup winners with the Montreal Canadiens by the time he joined the Leafs for the 1958-’59 season.  (I think he had played for a time with Chicago before joining the Canadiens.)  He put up a lot of points in Montreal, but was also known as one of the toughest (and meanest) players of his day.  He was Montreal’s Ted Lindsay—not the biggest guy in the world, but afraid of no one.

I remember at the time that Olmstead was looked up to in the Toronto dressing room because of his experience and championship pedigree with the Habs, and also due to his ‘take no prisoners’ approach to playing the game.  While I’ve heard some former Leafs (like the late Carl Brewer) dismiss the notion, many young Leafs of that time credit Olmstead with bringing a winning attitude to the dressing room.  He was known to hold teammates accountable, calling them out as necessary when they did not give their all.

Interestingly, Imlach named Olmstead an assistant coach at one point (while the winger was still a player) but Olmstead stepped away from that gig because he felt Imlach was not actually consulting with him in any meaningful way.

Olmstead helped the Leafs in a big way.  He was the ultimate corner man.   The club had some excellent veteran players in the late ‘50s like Tim Horton, George Armstrong, Allan Stanley, Bob Pulford and of course the then relatively unknown Johnny Bower. None of those guys had ever won a Cup, but when you combined that group with youngsters such as Frank Mahovlich, Dickie Duff, Carl Brewer and Bob Baun, you had the core of a heck of a team that was about to emerge as something special.

When Dave Keon and Bob Nevin joined the team in 1960-’61, those additions, along with the arrival of longtime Red Wing mainstay Red Kelly, made the Leafs a team to be reckoned with.

The Leafs made it to the finals in Olmstead’s first two seasons in Toronto, but they lost both times against Bert’s old club from Montreal.  But by 1961-’62, it was the Leafs year.  They worked their way past the Rangers in 6 games in the first round, and then beat the defending champion Blackhawks in the finals in 6 games as well, with Don Simmons filling in admirably in net for the injured Johnny Bower. (That was one of my happiest moments as a young Leaf fan, the night they won the Cup in Chicago in a nerve-wracking finish. I well recall watching that game on our little black and white television...)

Perhaps a tad ironically, Olmstead’s impact in that Cup year (at least in the playoffs) was modest, in part because he was hurt at the time.  (He played in only four playoff games and earned a single assist.)  But in reality the grizzled veteran was also on his last legs, though he was “only” 35 at the time.  (In those days, it was the relatively rare player who played until they were in their late 30s…)

He was placed on waivers in the summer of ’62, and picked up by the Rangers.  But rather than start over again in a new city, Olmstead retired.

He later re-surfaced as the head coach of the expansion Oakland Seals in that franchise’s first NHL season in 1967-’68, and in fact coached a number of ex-Leafs including Kent Douglas and Wally Boyer, as well as former teammates Bobby Baun and Billy Harris, if I’m not mistaken.  But he was not built to be behind the bench.  Too intense, too unforgiving of mistakes, perhaps.  I really don’t know.

Why this bit of nostalgia from me today?  Well, as many of you know, I love writing about my memories of Leafs of the past from my youth.  But I genuinely believe the Leafs could use a player much like Olmstead today.  A true veteran—and a winner.  Someone who could and would hold younger teammates accountable.  Someone who was not just a “goon” who played three minutes a night, but a versatile, skilled player who also would crash into the corners, use his elbows and fight for the puck.

His career point totals (just over 600, and about 60 more in the playoffs) may seem modest by today’s standards, but in the context of the time, he was a marvelous player, and tough as they came.

Where can we find a guy with five Cups as well as skill, toughness and leadership on his resume now?  I don’t know, but if the Leafs ever find someone like Olmstead, they should run to grab him.  That’s the kind of guy that can teach you “how to win”.