The Washingtons’ musical career was growing but was not enough income to support Jackie financially. An additional blow was Ormsby’s tragic death in a swimming accident in the summer of 1938. To better support himself and his musical dreams, Jackie worked as a sleeping car porter for the Canadian Pacific Railway as well as a factory worker, washroom attendant, and shoeshiner at the Fort Erie Racetrack. Washington’s employment as a sleeping car porter inspired a lifelong interest in trains and his musical talents fostered connections with touring musicians like Duke Ellington, Lionel Hampton, and Louis Armstrong.

Jackie also served in World War II. After his medical discharge in 1943, Washington looked for work. However, unwritten racial bars and discrimination made it hard for Black people to find factory jobs. Eventually, he got a job working at the American Can Company in Hamilton.

While working at the American Can Company, Jackie formed a new musical act with Sonny Johnston. The two men launched a weekly radio show as “The Personality Boys” on CKOC in Hamilton from 1943-1946. In 1948, Washington became Canada’s first Black disc jockey for CHML radio with his solo show, “The Jackie Washington Show” which was on air until 1953. Jackie was also sympathetic to local labour issues and performed for striking workers on the picket line during the Local 5 strike of 1950 in Hamilton.

Jackie regularly performed in Hamilton bars and local venues during the 1960s and joined the emerging folk music festival circuit in the 1970s. He was a staple at the Home County Folk Festival in London and the Festival of Friends in Hamilton during this time. His musical career also benefitted from folk music promoter Bill Powell, who introduced Washington to Toronto's Yorkville music scene in 1964 and started managing some of his bookings.

Despite some health problems, including a diabetes diagnosis in 1970, Washington toured extensively, playing in small venues across Ontario and Quebec. Jackie released his first album, “Blues and Sentimental” on Knights II records in 1976 with his brother Bobby backing on bass.

The release marked a new chapter of his musical career and Jackie became well-known as a versatile, skilled, and joyful musician. In addition to his own album, Jackie appeared on recordings by Duke Ellington, Lionel Hampton, Joni Mitchell, and Gordon Lightfoot. He also made his film debut in 1983 in the Sneezy Williams movie, “Hank Williams - The Show He Never Gave.”

During the late 1980s, Washington performed and toured as part of the trio “Scarlett, Washington and Whitely,” with Mose Scarlett and Ken Whitely. They recorded the album “Where Old Friends Meet” on Borealis Records in 1991. This album was nominated for a Juno award for Best Roots & Traditional Album. Washington also recorded additional albums with Borealis Records, including the famed “Midnight Choo Choo” in 1998.

Despite continuing health issues, Jackie continued to record and perform. He missed only one of the Festivals of Friends held in Hamilton between 1975 and 1995. After losing a foot to complications with diabetes in 1989, his friends organized a tribute concert for him in Toronto.

In his later years, Jackie was publicly recognized as a luminary of Canadian music. He was inducted into Hamilton's Gallery of Distinction in 1995 and into the Canadian Jazz & Blues Hall of Fame in 2002. He also received a Lifetime Achievement award from the Ontario Arts Council. Further, Washington was recognized with an honorary doctoral degree conferred by McMaster University in 2003. The Jackie Washington Rotary Park in Hamilton’s North End was named in his honour in 2004.

Jackie Washington died in Hamilton on June 27, 2009 at the age of 89. He was honoured by fellow musicians at a tribute concert at the Tivoli Theatre in Hamilton which featured artists including Jeff Healey, Garnet Rogers, and Tom Wilson. Jackie’s papers and music collection are held at McMaster University and his music continues to inspire generations of musicians.