*Deceased
| 1931-1933 | Homer Hiderbrand * | National Life of Vt. . |
| 1933-1935 | A.R.Ferguson* | Phoenix |
| 1935-1936 | J.A. Norris* | N.W. National |
| 1936-1937 | Andy Palm* | State Farm |
| 1937-1939 | Earl Lemonds* | Equitable Life/Iowa |
| 1939-1941 | Art Mitchell* | Penn Mutual |
| 1941-1943 | W.K. Beck* | New York Life |
| 1943-1944 | Martin Beckers* | Equitable/New York |
| 1944-1940 | Guy French* | New York Life |
| 1945-1947 | Edward H. Downs * | Midland National Life |
| 1948-1949 | George Lucas* | New York Life |
| 1949-1950 | M.O. Lee* | Midland National |
| 1950-1951 | Harry Denny* | The Travelers |
| 1951-1952 | Loftus H. Ward* | Bankers Life |
| 1952-1953 | John J. Stoia* | N.W. Mutual |
| 1953-1954 | Don Blumer* | Equitable of NY |
| 1954-1955 | Herman Ulrich* | Lincoln National |
| 1955-1956 | Webb Weir* | Equitable of NY |
| 1956-1957 | Ricahrd Kettering* | N.W. Mutual |
| 1957-1958 | Harold Grant | Central Standard |
| 1958-1959 | Norman Stordahl* | Lutheran Brotherhod |
| 1959-1960 | Viorel Stoia* | N.W. Mutual |
| 1960-1961 | J.D. Estes* | Western States Life |
| 1961-1962 | Jack Berghuis* | Provident |
| 1962-1963 | Paul K. Flanagan* | The Travelers |
| 1963-1964 | Elmer Bartling* | A.A.L. |
| 1964-1965 | Ralph Stiles* | Western States Life |
| 1965-1966 | Robert E. Richmond | Cont'l Assurance |
| 1966-1967 | M.A. Hoellwarth* | Provident |
| 1967-1968 | George F. Merkel | Lutheran Mutual |
| 1968-1969 | John K. Beegle* | N.W. Mutual |
| 1969-1970 | Howard Winstead* | Woodman Life |
| 1970-1971 | Thomas M. Seiler* | N.W. Mutual |
| 1971-1972 | Marvin Winter* | Nat'l Farmers Union |
| 1972-1973 | James E. Dardis* | Dardis-Richmond Inc. |
| 1973-1974 | Lyle F. Martin* | Western State Life |
| 1974-1975 | Dean Myers* | A .A.L. |
| 1975-1976 | Robert L. Goeman* | W. States |
| 1976-1977 | William B. Tyler* | N.W. Mutual |
| 1977-1978 | Dale Oleson* | Oleson Insurance |
| 1978-1979 | Philip N. Hegg* | Fidelity Union Life |
| 1979-1980 | Darrel D. Anderson* | State Farm |
| 1980-1981 | Jerome H. Gau | W. Mutual L & C |
| 1981-1982 | Thomas Larson* | Prudential |
| 1982-1983 | Rube Adam | Western States |
| 1983-1984 | Ronald Staebell | Williams Ins. Agency |
| 1984-1985 | Mark Heisner* | A.A.L. |
| 1985-1986 | Vincent Allard* | New York Life |
| 1986-1987 | Denny Rowley | Kundert-Williams Insurance |
| 1987-1988 | Dennis Jarabek | Woodmen Accident & Life |
| 1988-1989 | Dennis Westgard | Investment Centers |
| 1989-1990 | William McGreevy | Union Central Life |
| 1990-1991 | Rex L. Rolfing | Lutheran Brotherhood |
| 1991-1992 | Byron Bymers* | Equitable Life |
| 1992-1993 | Joe Hanson | Woodmen Accident & Life |
| 1993-1994 | Leland Stoddard | Aid Assoc. For Lutherans |
| 1994-1995 | Fredrick Meyer | Western States Life |
| 1995-1996 | Paul Steffen | Ohio National Life |
| 1996-1997 | Denny Sand | American Family |
| 1997-1998 | Alan Bernhagen* | Life Security Agency |
| 1998-1999 | Jim Waggoner | Modern Woodmen of America |
| 1999-2000 | Dean Karlen | Security Financial Life Ins. Co. |
| 2000-2001 | Rosie Harrington | American Family Life Ins. Co. |
| 2001-2002 | Robert French | Transamerica Insurance Investment Group |
| 2002-2003 | Larry Jacobson | American Family |
| 2003-2004 | Courtney Livingston | Thrivent Financial |
| 2004-2005 | Steve Bass | Life Security Agency |
| 2005-2006 | Michaele McGreevy-Lawler | McGreevy Associates |
| 2006-2007 | Terry Anderson | Anderson Insurance |
| 2007-2008 | Scott McDonald | Modern Woodmen of America |
| 2008-2009 | Merle Wollman | Wollman Insurance Group |
| 2009-2010 | Tim Dardis | Principal Financial Group |
| 2010-2011 | Doug Leighton | Dakota Gold Insurance, Inc. |
| 2011-2012 | Michael "Milo" Hagen | Hagen Ins. |
| 2012-2013 | Joseph Sztapka | Modern Woodmen of America |
| 2013-2014 | Eddie Heisinger | American Family Ins. |
| 2014-2015 | Jeff Skinner | Skinner Financial Services |
| 2015-2016 | Calvin Sievers | Thrivent FInancial |
| 2016-2017 | Blaine Anderson | Farmers Union Insurance |
| 2017-2018 | Ken Beer | Modern Woodmen of America |
| 2018-2019 | Jessica Blum | Anderson Insurance |
| 2019-2020 | Lonnie Tutsch | Modern Woodmen of America |
| 2021 | Andrew Bartling | Modern Woodmen of America |
| 2022 | Jennifer Soma | Thrivent |
| 2023 | John Lawler, LUTCF | McGreevy & Associates |
| 2024 | Matthew Berger, LUTCF, LACP | Western Dakota Insurors, Inc |
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