Illustrator takes Bruins fans on ‘Historic 100’ nostalgic tour

One of Boston’s greatest hits was “Don’t Look Back.”

There’s ironic genius and simplicity in Tom Scholz’s signature anthem.

His band was named in honor of a Hub entrenched in history.

Past revolutions. Past glories. Past heroes.

There’s been a great deal of looking back these days in and around Boston.

Why not?

It can hurt to look at the present.

Tom Brady delivered his victory speech at Gillette Stadium last Sunday at halftime. After the
Patriots trailed 16-0 in the first quarter.

It was as if Luke Skywalker came “home,” claimed his NFL birthright, and declared final victory
over the Evil Empire/former coach.

Yoda approved. The Patriots played just well enough to lose.

Brady, at 46, is now the most wanted man in Gotham City since Bane thanks to the four-snap-
and-out departure of Aaron Rodgers.

Gang Green is littered with millions who would happily trade their first born (pet or person) in
exchange for Brady joining the Jets.

Red Sox and Yankees fans – the few who showed up at Fenway Park this week – had no choice
but to embrace the past as these former titans of the diamond fought for last place.

The Red Sox and Yankees once literally slugged it out for playoff berths and pennants. The cost
of tickets that could be had at Fenway Park often flirted with four figures.

The get-in price this week bottomed out at $1, according to Boston Herald baseball muse
Gabrielle Starr.

Inflation drove that figure to $3 by Wednesday. Freebies proliferated on social media.

When Chaim Bloom was put out of our misery, the name Theo Epstein immediately proliferated
across talk radio and social media.

Sam Kennedy told us, sadly, that Theo is not walking through that door on Jersey Street.
The Celtics flaunt their addiction to the past. It’s an all-purpose crutch whenever someone
mentions they’ve added just one banner since “Crocodile Dundee.”

The Bruins, however, are poised to win the “About Face” prize this fall.

This is the Bruins Centennial.

Every seat at TD Garden comes with its own rear-view mirror.

The 2023-24 season will be Boston’s 100th in the NHL. Given the Bruins’ catastrophic exit from
the playoffs last spring, and the unceremonious gutting of the roster this offseason, 1924 looks
a lot more appealing than 2024.

The Bruins loaded the 2023-24 calendar with banner events throughout their milestone season.

None include another Stanley Cup banner being raised to the rafters.

The Cup was busy crisscrossing the Bay State this summer, thanks to Las Vegas coach Bruce
Cassidy and center Jack Eichel.

The Bruins unveiled their “Historic 100” Tuesday. This, by the way, is just a precursor to the All-
Centennial Team. You’re going to have to wait for the Centennial Gala on Oct. 12 for those
names to be unveiled.

Any list of 100 anything is impressive. This one was the product of an expert panel of which I
was not a member.

There were pockets of feigned outrage over some obscure omissions. Not here.

Beyond the talent of the players honored, what made this list exceptional was the manner in
which the Bruins chose to present it.

Fitting a list spanning the past 100 years, the Bruins opted to go old school.

Each player chosen to the “Historic 100” was hand drawn and illustrated by Winchester artist
and TD Garden usher Dave Olsen.

There were no computers in 1924. And there were no computers used in creating the images of
the “Historic 100” in 2023.

“Pen, ink. Watercolor markers,” Olsen told me when asked for his tools of choice.

Olsen began sketching hockey players for the Woburn Daily Times in 1977 while he was still in
high school. His work appeared in multiple newspapers over the ensuing years.

He drew the covers of several Bruins media guides. He’s been an usher at TD Garden for 10
years and took the job, in part, to get his work in front of the right people in the Bruins front

Olsen was tasked to draw the players on the “Historic 100” by Bruins Creative Services Director
Mark Majewski.

The Bruins had nearly a century to create this list. Olsen only had about two months to individually
draw each of the 100 players honored.

On his busiest days, Olsen was able to knock out five players: “I started drawing at 9 a.m. and
went until midnight.”

He realized this wasn’t an insane or impossible task about the time he finished his 50th drawing.

When he began drawing in the spring, he did not have the complete list.

He knocked off the obvious choices first.

Bobby Orr. Phil Esposito. Patrice Bergeron. Ray Bourque. Derek Sanderson. Stan Jonathan.

The Bruins gave Olsen reference photos of each player. But some choices were left to the artist.

His image of Orr features a thick, busy head of brown hair straight out of “The Partridge

“I like the years Orr had that look. Orr had a crew cut when he started with the Bruins. I wasn’t
going to draw Orr in a crew cut,” Olsen said.

Heresy avoided.

The dark mane on Sanderson sits above a face featuring the slightest of winks.

Perhaps Turk was headed home at 5 a.m. after another night of “sensational fun” (his words,
not mine) at Daisy Buchanan’s.

Of course, there are critics. “Someone posted, ‘Who drew this picture of Bergeron?’ ” Olsen said.

Drawn illustrations are not meant to be a perfect likeness, but rather the best depiction of each
player in his era.

Olsen scored 33.33 hat tricks this time.

“I am putting my artwork out there, for sure. It’s a close representation,” he said. “They are
hockey players. Some of these guys are beat up. They’re not exactly George Clooney’s.”

Bill Speros (@RealOBF and @BillSperos) can be reached at

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