Ward Pease's son and middle child was 
b. December 13, 1911, at the family home on the Lett Family Homestead, south of Sandwich, Illinois, and into his Family: Father, Ward Pease Montgomery. Mother: May Belle Fitzgerald Montgomery. Sister Marilla May, age 3. His sister, Mary Louise, would arrive 1913.  

Some events and timeframes of his good life:
  • 1917-1922 - Started school September, 1917. Attended a rural schoolhouse reportedly just to the east of the Lett Homestead Farm about one-half mile. After leaving the Lett Homestead Farm, attended the one-room "Little Red Schoolhouse" on the road south of Base Line Road (now Orchard Road), west of Montgomery, IL, He attended with his older sister Marilla. The "Kick" School, as it was called, was next to the "Kick" Cemetery. Younger sister Mary Louise attended this school briefly. Lived on the Base Line Road farm with the family's pet hens, their Collie, "Flossie", and Shetland pony, "Bud". Used to ride him bareback and one time his dad hitched Bud to a little cart and Bob and his sister, Mary Lou drove him to the little red schoolhouse. The family later moved to a farm just north of Aurora on Randall Road, just north of Galena Street, where today there are only pine trees to suggest the location. Attended the nearby rural "Randall School" with his sister, Marilla. A photo of their school class taken on the Fox River island at Geneva, IL, attests to this.
  • Late 1922 - early 1923 - Moved from the Randall Road farm to live on Blackhawk Street near Greenland School, west side of Aurora, IL. His Father, Ward, started selling real estate, taking commercial artist correspondence classes and did a little land surveying.
  • 1923 - July 2 - His Father, Ward Pease Montgomery, dies of a ruptured duodenum in Aurora, Illinois, after only a week in hospital. Had apparently began ulcers while still living on the farm(s).
  • 1923-1924 - Lived with his Mother and sister Mary Louise and his Uncle Harold at the farm of maternal grandparents, James and Ida (Compton) Fitzgerald, north of Wheaton, Illinois. Went to grammar school there. Sister Marilla stayed in Aurora in high school on west side of Aurora through graduation.
  • 1924 - Moved from Grandparent's farm north of Wheaton back to Aurora.
  • 1925 - Reunited as a family unit with Mother and 2 sisters after sister Marilla's High School Graduation.
  • 1924-1925 - First job - paper route
  • 1925-1929 - Attended East Aurora High School, Aurora, IL. Interested in music, art / illustration, as was his father. In an autobiography at age 14, he expressed desire to become a commercial artist one day, as did his father at the end of his life.
  • 1926-1928 - Purchased first second-hand snare drum with $5.00 from paper route.
  • 1928-1929 - Worked after school and Saturdays at Fisher's Bakery in Aurora for 25 cents per hour during last year of High School.
  • 1929 - Began playing dance jobs using his expanded drum set, added to during high school with money from the Bakery job. October 1929 - Stock Market Crash.
  • 1929, June - Graduated East Aurora High School, East Aurora, IL.
  • 1931 - August - Living with family in an up/down duplex on Evans Avenue. Contracted polio of the lower extremities following a long hot day, having had a headache all day and playing a band job. Doctored daily by a Doctor Lindbergh, Osteopath, and his family with the aid of fluids, fruit and many massages. Recovered from polio enough to be able to walk independently and play drums - but never to run again. Took drum lessons in Chicago for a brief time after the polio - paid for by Mother.
  • 1932, October 22 - Bob's Band, The Fidgety Five, a novelty band, won first place in the district finals of the WLS Radio / Paramount Radio contest at the Paramount Theater in Aurora, IL, winning $75 and an opportunity to perform before a live audience on the air on November 20, 1932, at the WLS Radio Studios in Chicago, IL. Paying in the band were: Wiley, bass; Russ Lindgren, guitar; Jack Pfeffers, trumpet; Rogers, sax, Montgomery, drums. One of the WLS judges eventually bought the WLBK radio station in De Kalb.
  • 1932, November - Grandpa Fitzgerald died, Grandma Fitz came to live with the family.
  • 1932-1933 - Bob Montgomery and His Band - played at small clubs like the Prima Gardens in and around the Fox River Valley, ala Geneva and Aurora, IL. Places like the Fox Valley Gardens and a nice club on the east side of Geneva.
  • 1933 - Family moved to 440 Weston Street - a four-bedroom house near Copley Hospital - with the expanded family, including Grandma Fitzgerald. Family had lived in houses / apartments / duplexes on Grant Place (near the coffee house), South Avenue two times (by themselves and once with his Grandfather and Grandmother Montgomery and Edith and Jessie, etc.), Root Street and Benton Street near the high school - all on the east side of Aurora.
  • 1933 - Played drums in a small band (his band?) at a club north of Aurora - The Paramount - in Geneva. At home in Aurora, he took on a roommate and fellow band member named Harold O'Brien.
  • 1934-35 - Traveled with Artie Collins' Band to, among other places; Detroit, Chicago, Nashville, Cleveland, Akron, Syracuse, Buffalo, Columbus, Youngstown, Louisville. In a letter to his Mother in late summer, 1935, he writes from The Garfield Hotel in Cleveland of having nothing to do while waiting to leave for "a one-nighter in Bascom, OH, then to Youngstown for 2 weeks at $20 a week - a "living wage", and then to the "Roosevelt" in Pittsburgh, the Van Cleve in Dayton, the Gibson in Cincinnati or the Carter in Cleveland." The bookings didn't sound reliable - confusion was blamed on the bookings office, as per Collins. His money was shrinking, too.
  • 1935 - November - Had left playing with Artie Collins' Band to play with Harold Menning's band and was living in Appleton, Wisconsin. Bob talked to Menning about hiring Obie and in mid-January 1936, Obie and Bob's sister, Mary Lou, "joined" the band. Appleton was headquarters for the band and they played in surrounding towns, traveling in a bus. Returned home in time for his sister Marilla's wedding at Thanksgiving-time.
  • 1935-1936 - Played drums in the Harold Menning Orchestra. Traveled by bus to surrounding towns. Maybe got into Menning's orchestra by knowing someone in the band, as it was when he got his brother-in-law, Obie, into the band. Owned a Paramount label 78rpm vinyl record, dated as recorded in 1928 in Port Washington, WI, of Harold Menning's Orchestra's "My Suppressed Desire".
  • 1936 - January-July - Brother-in-law Obie also played with the Menning orchestra and then moved back to Illinois. Originally lived with Bob Tewkes and another man in Appleton and slept on an open sleeping porch until Obie and Lou came up to Appleton. Lived with Obie and his sister Mary Lou and their son "Jackie" in an apartment in a private residence in Appleton. Returned to Aurora after the band had apparently broken up.
  • 1939-1943 - During this time worked at a men's clothing store in Aurora (waited on Buster Crabbe of "Flash Gordon" movie fame). After that he went to work for Montgomery Ward's Department Store in De Kalb. Used to have lunches at "The Cabin" tavern and restaurant on Lincoln Highway.  He met one Victor McMenamin and consequently rented a room in the home of Vic's parents, John and Martha McMenamin (and Vic's 2 sisters, Barbara and Clare), on Augusta Avenue in De Kalb.
  • 1940 - August 28 - Recorded on a Silvertone Label disc; "Exactly Like You" and "Medley: Whispering / On The Alamo / More Than You Know," with vocals by Bob on the Medley. Band recorded with: unknown.
  • 1943 - September 4 - Married Barbara Jean McMenamin, Vic's sister, while earning $ 35.00 a week at Bowman's.  They rented a downstairs apartment on West Locust Street in De Kalb.  Rent was $32 a month.
  • 1940-1943 - Worked for Montgomery Wards Store in downtown De Kalb, IL.
  • 1943-1946 - Worked for Bowman Shoes, downtown De Kalb, IL.
  • 1944 - Moved to rented house on Oak Street in De Kalb. All 4 children brought home to this house.
  • 1946-1966 - Manager of Bowman Shoes.
  • 1953 - Bought house at 640 North 5th Street in De Kalb.  Barbara lived there until October, 1984.
  • 1966-1971 - Bookkeeper for Chas. Ackerman Co. stores, a group / chain of women's clothing stores.
  • Retired 1971.
  • Played drums with various bands and combos over the years, nearly every Saturday night, every New Year's Eve for sure, until about 1974 when he put down "the sticks".
  • 1943 - November - Moved to 112 East Oak Street with a baby on the way.  Rented the two-bedroom house from Mr. and Mrs. Wilson.
  • 1944 - June 5 - First child born - Jean Marie - at St. Mary Hospital, De Kalb, IL.
  • 1946 - June 13 - First son born - Richard James - at St. Mary Hospital.
  • 1948 - October 6 - Second son born - William John - at St. Mary Hospital.
  • 1950 - March - James Robert's Grandmother, Ida Compton Fitzgerald, died in Aurora from pneumonia, a week after falling and breaking her hip.
  • 1953 - February 23 - Third son born - John Robert - at St. Mary Hospital.
  • 1953 - Summer - Purchased and moved into 3-bedroom, 1 bathroom house at 640 North 5th Street, De Kalb, IL.
  • 1955 - Father-In-Law, John McMenamin, dies.
  • 1958 - June - daughter Jean Marie graduates from St. Mary Parochial School.
  • 1958 - Summer - Remodeled house on North 5th Street, adding a large living room on the south of the existing dining room.  The previous living room became a 4th bedroom.
  • 1960 - June - son Richard James graduates from St. Mary Parochial School.
  • 1962 - June - daughter Jean Marie graduates from De Kalb High School, attends Northern Illinois University in the Fall.  
  • 1962 - June - son William John graduates from St. Mary Parochial School.
  • 1964 - February 8 - daughter Jean Marie marries Joe Thomas Bjorn.
  • 1964 - June - Richard James graduates from De Kalb High School.  Shortly thereafter begins attending Elgin Community College, Elgin, IL.
  • 1965 - Summer - Bathroom / Kitchen addition to rear of house at 640 N. 5th Street.
  • 1966 - February - Travels with Dee Palmer and friends to New Orleans for a few days to enjoy the jazz!
  • 1966 - Leaves Bowman Shoe Store employment after 23 years.
  • 1966 - Begins working for Charles Ackerman Stores, a chain of women's clothing stores, as bookkeeper.
  • 1966 - May 26 - First grandchild born - Jeffrey Thomas Bjorn - to Jean Marie.
  • 1966 - June 8 - William John graduates from De Kalb High School.  Attends Northern Illinois University in the Fall.
  • 1967 - June - Richard James graduated from Elgin Community College and began a 34-year employment with Commonwealth Edison, starting out as a meter-reader.  Richard enrolled at NIU in the fall.
  • 1967 - Fall - Son Richard James enrolls at Northern Illinois University, graduating in December, 1983, with a Bachelor of Science Degree in General Studies.
  • 1968 - September 4 - Celebrates 25th Wedding Anniversary.
  • 1968 - September 7 - Richard James marries Jeanne Lorraine Allen.
  • 1968 - January 23 - Second grandchild born - Eric Clifford Montgomery - to Richard.
  • 1968 - May - Son Richard James drafted into USArmy, sent to Viet Nam.
  • 1968 - June 12 - Mother May Belle Fitzgerald Montgomery dies in De Kalb, IL.
  • 1969 - April 26 - Son William John marries Pamela Whitson.
  • 1969 - November 3 - Son William John drafted into USArmy, sent to Korea.
  • 1970 - June 18 - First Granddaughter born - Stephanie Lynn Montgomery - to William.
  • 1970 - November - Son Richard James returns from USArmy, Viet Nam.
  • 1971 - June - Son John Robert graduates from De Kalb High School.  Attends Kishwaukee College in the Fall.
  • 1971 - June - Son William John returns from USArmy, Korea.
  • 1973 - January 31 - Grandson born - Scott William - to William.
  • 1973 - January - Son William graduates from Kishwaukee College with an Associates Degree.
  • 1973 - James Robert Montgomery retires from Chas. Ackerman Stores after 5 years employment, age 62.
  • 1973 - June - Son John graduates from Kishwaukee College - transfers to University of Illinois, Champaign-Urbana.
  • 1973 - September 4 - Celebrated 30th Wedding Anniversary.
  • 1974 - April 23 - Grandson born - Spencer Fitzgerald Montgomery - to Richard.
  • 1975 - June - Son John graduates from University of Illinois with BA.
  • 1976 - June - Son John graduates from University of Illinois with MA.
  • 1976 - August 26 - Son John marries Kristi Pielstick.
  • 1977 - Spring - contracts Prostate Cancer.  
  • 1977 - Summer - Travels with his wife Barbara to England and the Island of Majorca, Spain, to visit Barbara's sister, Mary Claire.
  • 1977 - Summer - Radiation treatments for the cancer and a somewhat primitive, uninformed treatment of castration do not alleviate the "disease.
  • 1977 - September 23 - Granddaughter born - Jennifer Pielstick - to John Robert.
  • 1977 - November 22 - Granddaughter born - Carolyn Martha - to William John.
  • 1977 - December 11- Grandson born - Joe Ryan Cornish Bjorn - to Jean Marie and Joe Bjorn.
  • 1977-1978 - A 4-month, at-home, increasingly bedridden decline, with loving care provided by in-home nursing, his children rotating to assist their mother on weekends, and the faithful devotion of his wife Barbara.
  • 1978 - March 12 - James Robert Montgomery dies of Prostate Cancer 
  • 1978 - March 15 - Buried in St. Mary Cemetery, De Kalb, IL.
  • Following his death, another 2 children, Martha and Robert, were born to Son John Robert, and later 2 step-grandchildren to Son Richard, 8 grandchildren and 2 step-grandchildren to William John, and 1 grandson to John, as of this writing, all occasions causing regrets that Bob was not present to help celebrate.
  • And the beat goes on . . .

James Robert and Barbara Jean McMenamin Montgomery's children are: 
  • Jean Marie MONTGOMERY
               b 5 June 1944
  • Richard James MONTGOMERY
               b 13 June 1946
  • William John MONTGOMERY
               b 6 Oct 1948
  • John Robert MONTGOMERY
               b  23 Feb 1953

(It is William John Montgomery from whom this research, information and website is developing.)
/\    May 6, 1951
Bowman Shoe's Front Windows, June 15, 1965
/\    The Fidgety Five, 1932
Bowman Shoe's Front Windows, June 15, 1965
Class of 1929, East Aurora H.S., Aurora, IL
James Robert Montgomery
April 1969, 
age 57
Click one of the music players below to hear some of Bob's favorite music, even one of his recorded
\/        'hits', recorded 1940, re-mastered 2004.    \/
Jo Stafford, 1952, favorite female singer.
String of Pearls - Harry James, Benny Goodman, Stan Kenton
Drum Boogie - Benny Goodman, Gene Krupa (favorite drummer)
Medley - "Whispering / On The Alamo / More Than You Know", 1940, orchestra unknown, solo: Bob Montgomery.
 Harold Menning's Orchestra bandstand, 1935-1936  ^
Artie Collins' Orchestra sample gig clippings, Ohio, 
Bowman Shoes, 1946, DeKalb, IL
Bowman Shoes, 1946, DeKalb, IL
Barbara Jean McMenamin Montgomery, 2001
Bob in his Harold Menning Orchestra tuxedo.
Drum logo / insignia is the same in both photos  >
L to R: John Robert, Barbara Jean, Jean Marie, Richard James, and William John Montgomery, 
1 Sep 1997
A Montgomery Family Genealogy
As recorded and developed by W.J. Montgomery