When the Chicago Black Hawks (then two words) acquired Tony Esposito from the Montreal Canadiens in the intraleague draft on June 15, 1969, the move received almost no attention. After all, the Black Hawks had finished last in the East Division in 1968-69, and Chicago sports fans were focused on the first-place Cubs.
But Esposito turned out to be one of the best investments general manager Tommy Ivan ever made. For $25,000, he got a franchise goaltender for the next 15 years and a future Hockey Hall of Famer. Esposito, whose older brother Phil had been traded by Chicago to the Boston Bruins two years earlier, won the Calder and Vezina trophies in his first season with the Black Hawks, who went from last place to first in the East. He finished the 1969-70 season with 15 shutouts, a total unmatched since then, and a 2.17 goals-against average to help Chicago go from worst to first in the East.
Unlike his older brother, Tony Esposito opted to play college hockey and was a three-time First-Team All-America selection before turning pro with the Canadiens. He was also among the early practitioners of the butterfly style of goaltending, which fit his athleticism and ability to quickly get up and down, side to side.
Esposito got the Black Hawks to the Stanley Cup Final in 1971 and 1973, though they lost to the Canadiens each time. When he retired in 1984, Tony owned the Black Hawks' records for wins (418) and shutouts (74), marks that still stand.
Video: Tony Esposito won Vezina, Calder in 1969-70
In his NHL100 profile of Esposito, author Bob Verdi writes about how he turned a rocky start with the Black Hawks into a season for the ages.
"It did not begin well. Esposito was raked 7-2 by the St. Louis Blues in the season opener. The Black Hawks started 0-5-1 and fans were restless. But the Black Hawks went to Montreal, Esposito shut out his former team and the transformation in Chicago began to gain traction. The Black Hawks, just a .500 team by early January, embarked on a remarkable streak, losing three games in February and only one in March.
"On the final night of a frenetic regular season, the Canadiens visited Chicago Stadium in a state of desperation. They had to either win or score five goals to secure the last playoff berth via the tiebreaker. After the Black Hawks opened a 5-2 lead, Montreal coach Claude Ruel sporadically pulled [goalie Rogie] Vachon for a sixth skater. But it was the Black Hawks who feasted, scoring five empty-net goals for a 10-2 romp to complete an unprecedented worst-to-first finish.
The story of the winter, however, was Esposito. He was superlative, registering 15 shutouts -- still a record for any masked or unmasked man since the 1920s. He earned the Calder Trophy as best rookie and Vezina Trophy with a 2.17 goals-against mark. The Black Hawks had found a worthy successor to Glenn Hall."
Esposito was a special player to Harris.
"I was a goalie because Tony Esposito was my favorite player, and in a way, I owe my career as an artist to Tony as well," he said. "Esposito was my main subject from Grade 3 all through high school, and I would continuously draw him trying to perfect his pads and the Blackhawks logo. Needless to say, painting his portrait as one of the top 100 players of all time was a great thrill."
Like Esposito, Oates took the college route to the NHL. The Detroit Red Wings signed him as an undrafted free agent on June 28, 1985, after he excelled during three seasons at Rensselaer Polytechnic Institute, the only NCAA team that pursued him. He was a two-time First-Team All-America and helped RPI win the NCAA championship in 1985.
But on June 15, 1989, the Red Wings traded Oates and forward Paul MacLean to the St. Louis Blues for center Bernie Federko and forward Tony McKegney. It's a trade that still haunts then-general manager Jim Devellano, now a senior vice president of the Red Wings.
Oates wound up centering for Brett Hull, and one of the NHL's most dangerous scoring tandems was born. Hull scored 72 goals in 1989-90 and 86 in 1990-91, when Oates finished with 90 assists. Although Hull was on the way to a 70-goal season in 1991-92 and scored 50 goals in St. Louis' first 50 games, the Blues traded Oates to the Boston Bruins on Feb. 7, 1992.
The trade didn't slow Oates' production. He had NHL career highs of 45 goals, 97 assists (tops in the League) and 142 points for Boston in 1992-93. He also led the NHL with 69 assists while playing for the Washington Capitals in 2000-01, and again with 64 in 2001-02, which he split between Washington and the Philadelphia Flyers.
Video: Adam Oates NHL's fourth all-time assists leader
Oates is one of four players, along with Wayne Gretzky (13), Mario Lemieux (four) and Joe Thornton (two) who've had multiple 90-assist seasons. Since the draft era began in 1963, only Gretzky (2,857) had more points than Oates (1,420) among undrafted NHL players. Only three centers in League history -- Gretzky (1,963), Ron Francis (1,249) and Mark Messier (1,193) -- had more assists than the 1,079 Oates had in 1,337 NHL games.
In his NHL100 profile of Oates, author Bob Duff talks about the effect the trade from Detroit to St. Louis had on the NHL's great playmakers.
"Once Oates got over the shock of the move from Detroit, it proved to be the wake-up call he needed.
"'When I got traded I was really upset,' Oates admitted. 'It was heartbreaking. Detroit was my first team. You're sentimental. You don't think you're ever going to leave. (Red Wings owner) Mr. [Mike] Ilitch was fantastic the way he treated the team.
"'But it gave me the chance to go to St. Louis and play with Brett and really establish myself in the League. I think it jump-started my career.
"All the way to the Hockey Hall of Fame, where Oates was inducted in 2012."
Oates played for seven NHL teams, but Harris said he ultimately decided to paint him in the colors of the Boston Bruins.
"Adam Oates is another top 100 player who had a great run with several different teams. In the end, I was happy to paint him in a Boston uniform," he said. "His days with the Bruins playing alongside Ray Bourque were some of the most exciting hockey I can remember."