Dennis "Cutty" Wise is a fictional character on the HBO drama The Wire, played by actor Chad Coleman. Wise is a reformed criminal who is striving to create a boxing gym for neighborhood children. There was a real contract killer named Dennis Wise, who is serving a life sentence in prison.

The nickname "Cutty" originates from his serving time in the Maryland State Penitentiary in Jessup, Maryland, which was nicknamed "the cut." Cutty is known as a legendary soldier in Baltimore's drug trade coming to the end of a fourteen-year prison sentence when Avon Barksdale and Wee-Bey Brice arrived at the prison. Cutty is 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 approaches Cutty with an offer of work shortly before his release.

Barksdale lieutenant Shamrock gives him a homecoming gift in the form of a package of narcotics. After observing a street dealer for a time, Cutty approaches him and offers to supply him for a cut of the profit. The dealer, Fruit, takes Cutty up on his offer but refuses to pay him when Cutty returns for the profits.

Cutty turns to work as a day laborer with a landscaping crew to get by. He tries to track down his ex-girlfriend, Grace Sampson, to reconnect and finds her working as a schoolteacher. She puts him in touch with her church deacon to help him find work, but resists any other involvement.

The deacon suggests that Cutty study to obtain his GED, but Cutty sees this as too difficult and, despite his initial hesitation, begins 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 earns the respect of Avon's primary enforcer Slim Charles, who throws a welcome home party for Cutty.

He works with young soldiers Sapper and Gerard to track down a thief in the Barksdale organization, and his cunning allows them to quickly identify the culprit. Cutty is appalled when the younger soldiers almost kill the young dealer, believing a warning beating would be sufficient to modify his behavior but keep him fit to work for them. A turf war between the Barksdales and new power Marlo Stanfield provides 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 "the game" in him, which he tells Avon that he's leaving the crew, 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.

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