Some others' thoughts...
THN's selections for Conn Smythe (from Great Debates, 2004)
1918 Alf Skinner
1920-21 Jack Darragh
1922 Babe Dye
1923 Punch Broadbent
1924 Howie Morenz
1925 Jack Walker
1926 Nels Stewart
1927 Alex Connell
1928 Frank Boucher
1929 Tiny Thompson
1930 George Hainsworth
1931 Johnny Gagnon
1932 Charlie Conacher
1933 Ivan Johnson
1934 Lionel Conacher
1935 Baldy Northcott
1936 Normie Smith
1937 Marty Barry
1938 Gordie Drillon
1939 Bill Cowley
1940 Phil Watson
1941 Milt Schmidt
1942 Syl Apps
1943 Sid Abel
1944 Toe Blake
1945 Frank McCool
1946 Elmer Lach
1947-48 Ted Kennedy
1949 Turk Broda
1950 Chuck Rayner
1951, 1953, 1958 Maurice Richard
1952 Terry Sawchuk
1954 Red Kelly
1955, 1964 Gordie Howe
1956 Jean Beliveau
1957 Bernie Geoffrion
1959 Marcel Bonin
1960 Jacques Plante
1961 Pierre Pilote
1962 Tim Horton
1963 Johnny Bower
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TDMM followed up with this...
Different selections by the Retro Conn Smythe Project
1919: Lalonde (THN doesn't list anyone, I assume because the finals were cancelled)
1933: Cecil Dillon
1943: Jack Stewart
1945: Ted Kennedy
1953: Ed Sandford
1954: Terry Sawchuk
1962: Stan Mikita
1964: Bob Pulford
The HHOF project has been criticized for including a player from the losing team too many times - Normie Smith in 1936, Gordie Drillon in 1938, Chuck Rayner in 1950, Maurice Richard in 1951, Ed Sandford in 1953, and Stan Mikita in 1962. The THN list gives the 1953 and 1962 Smythes to players on the winning team which is probably more realistic.
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Now, me: I remember years ago someone said the Retro Conn Smythe thing was being taken off of wikipedia and maybe off of somewhere else too...I'm certain that we have it memoralized somewhere...but with the board migration, I'm not sure where or if we care...