Cutty is known as a legendary soldier in Baltimore's drug trade. He was coming to the end of a fourteen-year prison sentence when Avon Barksdale and Wee-Bey Brice arrived at the prison. Cutty was well respected by Avon and many others in his organization for work he performed before going to prison, including murdering someone and then phoning the police from the scene of the crime. Avon approached Cutty with an offer of work shortly before his release. Barksdale lieutenant Shamrock gave him a homecoming gift in the form of a package of narcotics. After observing a street dealer for a time, Cutty approached him and offered to supply him for a cut of the profit. The dealer, Fruit, took Cutty up on his offer but refused to pay him when he returned for the profits. Cutty turned to working as a day laborer with a landscaping crew to get by. He tried to track down his ex-girlfriend, Grace Sampson, to reconnect and found her working as a schoolteacher. She put him in touch with her church deacon to help him find work, but resisted any romantic reinvolvement. The deacon suggested that Cutty study for his high school diploma, but Cutty saw this as too difficult and continued his landscaping. Despite his initial hesitation, Cutty began working with the Barksdale crew soon after his parole.
His effectiveness and intelligence as muscle is shown on several occasions when planning raids, hits and general menacing for Avon against competing crews. He quickly earned the respect of Avon's primary enforcer Slim Charles, who threw a welcome home party for Cutty. He worked with young soldiers Sapper and Gerard to track down a thief in the Barksdale organization, and his cunning allowed them to quickly identify the culprit. Cutty was appalled when the younger soldiers almost killed the young dealer, believing a warning beating would have been sufficient to modify his behaviour and kept him able to work for them.
A turf war between the Barksdales and new power Marlo Stanfield provided more work for Barksdale soldiers. Cutty and Slim Charles plan a raid on a Stanfield corner using a pincer movement. Their younger associates ruin their plan by striking too soon and Barksdale veteran Country is killed as a consequence. Cutty and Slim Charles decide to strike back alone but when their moment comes Cutty is faced with Fruit and finds himself unable to fire. It becomes clear to Cutty that he no longer has a tolerance for "the game," and he tells Avon as much when he tries to leave the crew by saying "I ain’t got it in me no mo'." Avon decides to let him leave, telling Slim Charles that Cutty still deserves their respect.
Wise then begins to build a new life by returning to landscaping and then opening a boxing gym at the deacon's urging. When he is unable to get sufficient funding to equip the gym, he approaches Avon to request the funding. Avon, a former amateur boxer, happily provides the money. Wise received political backing from the deacon's contact Reverend Frank Reid. Reid put Wise in touch with State Delegate Odell Watkins and Marla Daniels. Watkins had Daniels help Wise to get the permits he needed for the gym.
Wise connects with sergeant Ellis Carver through his efforts to encourage children away from drug dealing through sports, and the two develop a mutual respect. He has some success with local children, particularly when the turf war temporarily closes down a lot of the drug dealing business. In particular, one dealer named Justin gets strongly involved in the boxing. However, the turf war comes to a sudden end when Avon is arrested, and Cutty finds his gym quickly deserted as the children return to work. Cutty continues his efforts at personal reform despite this setback.
In season four Wise's gym is thriving and he has taken on a number of other trainers to work with the kids. Justin returns to training and begins to compete in local boxing matches. Wise receives a great deal of attention from the women of the neighborhood who are impressed with his community work. He begins to take an interest in training a boy named Michael Lee who he believes is a natural boxer. Michael rebuffs Wise's first offer of coaching. Wise has become adept at controlling the boys who use the gym and earning their respect. He is also having some success in his work as a landscaper having picked up a working knowledge of the Spanish spoken by most of his colleagues. The crew chief is so impressed with Wise that he offers to make him a partner in the business and put him in charge of a second crew but Wise refuses so that he can focus on the gym. Later on, Wise is shot in the leg while trying to convince Michael to leave the corner life. While in the hospital Wise is instrumental in getting Namond off the streets by getting Colvin a sitdown with Namond's father, Wee-Bey.
Wise appears one final time in the fifth episode of the series ultimate season, "React Quotes", when Michael brings Duquan 'Dukie' Weems to Wise's gym to get some training to confront Spider, who had previously beaten Dukie. Cutty tells Dukie that learning to fight won't keep bullies away, and he asks the boy why he thinks he's become a target. Dukie shrugs. Cutty understands the situation, though, and tells Dukie that the rules of the street don't apply to the rest of the world. But when he asks the coach how to get to that place, Cutty has no answer.
George Pelecanos is given credit with creating the character of Dennis Wise, based on unused notes from his novel Drama City, about a man getting out of prison after almost two decades. The idea fit well with the theme of the third season, "Reform", so the character was added. According to the book The Corner, there really was a violent criminal named Dennis Wise in Baltimore in the '80's, who served a long time in prison.