James A. Underwood Sr.

Lifelong Riverhead resident James A. Underwood Sr. passed away at the Westhampton Care Center on Nov. 10 at the age of 91. 

Jim was born in Riverhead on Nov. 27, 1929, to Bridget (Furlong) and Reginald G. Underwood Sr. After graduation from Riverhead High School in 1947, he graduated from Fordham University in 1951. Later that year he enlisted in the Army, serving from 1951 to 1953 as a commissioned second lieutenant. He married Irene Sidor of Aquebogue on New Year’s Eve, 1951. He worked as an independent title examiner for 60 years and was ever present in the record room of the County Center. 

A three-sport athlete at Riverhead (where he was named to the RHS Sports Hall of Fame), Jim was awarded a scholarship to Fordham University to play football. There he played as a freshman under legendary coach Vince Lombardi, and on the varsity was coached by Ed Danowski, a Riverhead alumni and former New York Giant. 

Jim’s biggest joy was spending time with his grandchildren and, later, great-grandchildren. He was a presence at any game, play or concert they were involved in. 

Jim was an avid sports enthusiast who fully enjoyed watching, coaching or participating in any activity that involved competition. He was well known in town for attending as many of his grandchildren’s games or matches as possible, and was a fixture at Riverhead basketball and football games. He coached CYO basketball and baseball and managed local softball teams RPIC and Doc’s Tavern in the ’70s and ’80s. One friend said Jim was “Riverhead royalty.”

He received the Basketball Officials Association’s Fan of the Year award one year, as he was apt to show up anywhere there was a game and knew the referees on a first name basis. 

As much as he was a fan, he loved to compete even more. He played in recreational volleyball leagues into his 70s and recreational basketball into his 60s. As he slowed down, golf became his next passion. At family gatherings he was always itching to get into the next ping pong game, corn hole contest, darts or whatever yard game was being played. 

As a member and past president of the Riverhead Lions Club he was Santa Claus in the annual Christmas parade in the ’70s and early ’80s. He decided to retire when his grandson Matt sat on Santa’s lap and claimed, “You sound just like my Grampy.”

Jim was a 38-year friend of “Bill W” and a mentor to many. There are those who would agree “Gentleman Jim” always had an extended hand and a twinkle in his eye and a welcome ear. 

He was predeceased by his wife in 1981 and his brother, Reginald G. Underwood, in 2020. He is survived by his children, James Jr. (Carol), Cathy Velys (Michael), Maureen (Tom), Terry Messina (Sal), Diane Rheaume and Michael; and his sister, Elizabeth Burns. He leaves his grandchildren, Jennifer, Michael, Timmy, Megan, Jessica, Kate, Ryan, Courtney, Matthew, Anthony, Alicia, Samantha, Jake, Mariah, Joanna and Mykaela. He was blessed with 10 great-grandchildren, Ellie, Sammy, Annie, Sophie, Ethan, Emma, Calvin, Franklin, Alepoi, Mason, and another due in December.

The family received visitors Nov. 14 at McLaughlin Heppner Funeral Home in Riverhead. The funeral Mass of Christian Burial was celebrated Nov. 15 at St. John the Evangelist R.C. Church in Riverhead. Burial followed at the parish cemetery.

Memorial donations to Peconic Bay Medical Center or St. John the Evangelist R.C. Church would be appreciated.

This is a paid notice.