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Flagg, Dick (2007)

Writer: Maine Baseball HOF
Maine Baseball HOF
Aug 12, 2019
2 min read

Flagg, Dick (07)

Dick Flagg is representative of a close-knit fraternity of umpires who came of age professionally in the 1960’s and 70’s and provided the authority and integrity essential to the thriving high school, legion and college baseball scene of that era.

Carroll Rines, Sonny Noel, Jack Redmond, Eddie Ainsworth, Hal Loubier and Leroy Rand – all “Men in Blue” who worked with Dick Flagg during his 48 years (and counting) of umpiring. An impressive list of veteran arbiters who took their job seriously and, although missing occasionally on a call, never failed to let you know where they, and you, stood.

Dick interest in baseball was life-long, although his actual playing days were limited to the 1946 Saco Valley League season. Dick graduated from Deering in 1947, served in the Army from 1947-48, came home and was recalled and served again from 1950-52 during the Korean conflict. He developed an interest in umpiring while in the Army. In 1960, at Jack Redmond’s urging, Dick took and passed the umpiring test and a career was launched which shows no sign of ending anytime soon.

Dick started out with JV and frosh games, gradually working up to high school varsity contests in the Triple C and Telegram Leagues and the Twilight League in the summer.

One of the more memorable games that found Dick behind the plate was the 1963 Twilight League Championship. Holy Cross (by way of Cheverus) phenom Dick Joyce took the mound for Peaks Island, opposed by Deering’s Dick Densmore, then attending Duke, who toed the slab for Harris Oil. Joyce bested Densmore 1-0 in a game that did nothing to tarnish the sterling reputation of both pitchers.

Dick’s rapid development into a top-knotch umpire caught the eye of Sonny Noel who recommended Dick to the college teams. Dick started working the Colby-Bates-Bowdoin series in 1968 and added several other Maine colleges to his resume in the 1970’s.

At the height of his productive career, Dick would often work 5 games a week and doubleheaders on Saturday and Sunday. In those days, umpires were more collegial and would often drive to the games together. (“Whoever had the plate would drive”). A close camaraderie developed among this band of brothers who would dissect that day’s game on the drive home and sharpen their game calling skills.

Dick began to pare back his arduous schedule in the late 1970’s but still, at the age of 78, manages to do 25-30 games a year. He jokingly vows to catch long-time friend and mentor Jack Redmond’s record of 50 years of umpiring and, now in his 48th year, is poised to accomplish that soon. By his own conservative count, Dick figures he has umpired over 2,000 games.

Dick went to work for Northeast Airlines (which later became Delta) in 1956 and retired in 1991. Dick and his wife, Patricia live in Portland as do Dick’s three children.

Dick regrets only that the commitment to umpiring did involve a lot of time away from his family. The life-long friendships and the quiet pride that comes from serving as a true steward of the game’s rules and traditions provide priceless consolation as does the recognition of his contributions today by the Maine Baseball Hall of Fame.

 
 
 

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Meet the 2026 Maine Baseball Hall of Fame inductees
Portland Press Herald 4/10/2026
https://www.pressherald.com/2026/04/10/meet-the-2026-maine-baseball-hall-of-fame-inductees/?copylink=true

 

Former St. Dominic and current Gray-New Gloucester coach Bob Blackman and Cony coach Don Plourde are among the 11 members of the newest class. Four coaches currently preparing for the upcoming high school baseball season are among the 11 inductees in the 2026 Maine Baseball Hall of Fame class.

Gray-New Gloucester’s Bob Blackman, Brewer’s Dana Corey, Hampden Academy’s Jon Perry and Cony’s Don Plourde are all part of the class that will be inducted on Oct. 4 at the Holiday Inn by the Bay in Portland. Blackman coached St. Dominic High School to nine state championships in 22 seasons before the school closed at the end of the last school year. He was named the coach at Gray-New Gloucester in September. Corey hit .359 at the University of Maine in 1971. He played two seasons in the Chicago Cubs system and has been the head coach at Brewer for 18 seasons.

Perry hit .381 at the University of Maine in 1981 and helped the Black Bears reach the College World Series. He has coached for the past 45 seasons at the high school, American Legion and collegiate levels. 

Plourde is in his 17th season as the coach at Cony High School and has been named the KVAC Coach of the Year five times. He has been coaching at various levels for more than 30 years. 

Others earning induction are: 

Al Cloutier, who has been involved in baseball in Augusta as a player, Cony High and American Legion coach, Babe Ruth League director and volunteer. 

John Kolasinski, who was a college coach at for 37 years, first at Husson and later at Siena Heights University in Michigan. He is a five-time New England Coach of the Year winner.

Mark Littlefield, a Portland High graduate, who is now in his 36th season working on the medical staff of the New York Yankees organization. 

Scott Littlefield, a Portland High graduate, who will be inducted posthumously. Littlefield coached at Florida State University and the University of Southern Maine before working for 34 years as a Major League Baseball scout, including 16 as a player personnel special assistant for the Texas Rangers.

J. Ronald Livington, who will be inducted posthumously. Livingston was an All-Star infielder for the semi-pro Presque Isle Indians in the Northern Aroostook League in the 1930 and 1940s. He also coached and was a director in the South Portland National Little League.

Mike McCullum, of Portland, who hit .338 at the University of Southern Maine and earned ABCA Division III All-American honors in 1999. 

Jim Taylor of Lewiston, who was a founding member of the Central Maine Board of Approved Baseball Umpires and was instrumental in starting the Maine chapter of the Collegiate Baseball Umpires Association.

Maine Baseball Hall of Fame day  Delta Dental Park aka Hadlock Field 7/19/2026
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