This week, the portraits of center Max Bentley and defenseman Brad Park are unveiled in the 20th installment.
Bentley played his first five seasons in the NHL with the Chicago Black Hawks (then two words), winning the Hart Trophy as most valuable player in 1945-46 and leading the League in scoring twice (1945-46 and 1946-47). But six games into the 1947-48 season, he was traded to the Toronto Maple Leafs for five players.
Bentley played six seasons in Toronto, helping the Maple Leafs win the Stanley Cup three times. Chicago didn't make the playoffs until 1952-53.
Bentley, who played his final season (1953-54) with the New York Rangers, finished his NHL career with 544 points (245 goals, 299 assists) in 646 games.
In his NHL100 profile of Bentley, author Bob Verdi details the shocking trade that sent Bentley from the Black Hawks to the Maple Leafs.
Video: Max Bentley won two scoring titles, Cup three times
"The monumental deal, transformational for the Chicago Black Hawks and Toronto Maple Leafs, reverberated throughout the NHL. Even President Clarence Campbell weighed in, saying he was 'astounded.' Bentley, after all, excelled in Chicago over five seasons, earning the Hart Trophy as most valuable player for the 1945-46 season and leading the League in scoring twice (1945-46 and 1946-47).
"Bentley, an electric performer, enjoyed immense popularity in Chicago. Nobody realized that more than Bill Tobin, president of the struggling Black Hawks. As Edward Burns reported on the big news that day in the Daily Tribune: 'The swap was broached more than a week ago in Toronto when Connie Smythe, managing director of the Leafs, suggested the deal after Tobin had gone there, screaming for help. Tobin was reported to have said that he wanted to 'talk it over with his mother.' At the time the reply was interpreted as a facetious comment by Tobin, who had been waving $100,000, not the deed to Bentley, in his belated effort to strengthen his cellar Hawks. Then he went to Ottawa and conferred with his mother.'
"The Maple Leafs sought the man, not the money, and the Black Hawks received forwards Gaye Stewart, Gus Bodnar and Bud Poile plus defensemen Bob Goldham and Ernie Dickens -- an entire unit, sans goalie. Stewart had won the Calder Trophy as best rookie in 1943 and Bodnar followed with the Calder in 1944. So the Black Hawks acquired quality and quantity, and needed both. Still, they would not make the Stanley Cup Playoffs again until 1952-53, by which time Bentley won the Cup three times in Toronto: 1948, 1949 and 1951."
Harris said painting Bentley in the blue and white of the Maple Leafs was a great experience.
"Max Bentley is a player that my father [a lifelong Maple Leafs fan] would talk often about when reminiscing about Toronto's past glory," he said. "My resource material was a black and white promotional photo, and bringing it to life with color was a lot of fun. The old felt Maple Leaf logo and woolen sweater were particularly rewarding."
Park, a physical presence at 6 feet, 200 pounds, was an excellent passer, puck-handler and shooter during 17 seasons with the Rangers, Boston Bruins and Detroit Red Wings.
Park made the NHL First All-Star Team five times and the Second All-Star Team twice. He was an eight-time runner-up for the Norris Trophy, finishing second mostly because of the one defenseman who was second to none and who also inspired him; Bobby Orr of the Bruins.
Video: Brad Park retired as leader in assists by defensemen
Park reached one Stanley Cup Final with the Rangers, but New York lost to Boston - its fiercest rival - in six games in 1972.
Three seasons later, Park, loved in New York and loathed in Boston, was traded to the Bruins.
Author Stu Hackel details the shocking trade in his NHL100 profile of Park.
"As Orr's knees weakened, causing the Bruins to seek a replacement, Boston GM Harry Sinden wanted Park. On Nov. 7, 1975, Sinden and [Rangers GM Emile] Francis engineered one of the biggest trades in NHL history, sending Park from the Rangers to the team he detested the most, meaning he'd play -- and star -- for fans who had detested him the most. (Jean Ratelle and Joe Zanussi also went to Boston in the trade, for Phil Esposito and Carol Vadnais.)
" 'There never was a hockey player so beloved in one city and so hated in another, only to have the roles reversed after eight years,' wrote hockey historian Stan Fischler.
"That isn't the whole story; Rangers fans had turned on Park prior to the deal, believing he was, as Sports Illustrated's Jerry Kirshenbaum described their dissatisfaction, 'overweight, overpaid and -- though only 27 -- maybe even over the hill.' Before that, they certainly had adored him since his rookie season."
Park went to the Stanley Cup Final twice with Boston, losing to the Montreal Canadiens in 1977 and 1978. He played his final two seasons in Detroit, making the playoffs each time, meaning he reached the postseason in each of his 17 seasons.
When he retired after the 1984-85 season, Park was the all-time assist leader among NHL defensemen with 683 and ranked third in goals (213) and points (896).
Harris said it was Park himself who chose to be painted in a Bruins jersey.
"Brad Park is a player who could be presented in either a Rangers or Bruins jersey," he said. "He had an amazing career representing both clubs, but ultimately he chose the black, gold and white of the Bruins."