Leander Sydnor

Biography

Sydnor joins the Barksdale detail after Cedric Daniels requests Lt. Cantrell's best detective to balance taking Roland Pryzbylewski. Partnered with Lester Freamon, Sydnor traces the Barksdale organization's paper trail. He also does undercover work, making hand-to-hand buys with Kima Greggs and Bubbles, though Bubbles finds his junkie disguise unconvincing. Sydnor identifies Avon Barksdale at the annual West-Side versus East-Side basketball game.

Season three

He tells Freamon, who becomes a mentor, that the Barksdale investigation is the best police work he has ever done. After the detail dissolves, Sydnor returns to his old district. When Daniels creates the Major Case Unit, he encourages Sydnor to transfer in, replacing spots vacated by Herc and Carver. Sydnor accepts and again investigates the Barksdale organization.

Season four

In season four, the unit adds Marlo Stanfield to their investigation alongside the Barksdale money trail. With Daniels promoted to Major, Freamon becomes de facto commander and picks Lieutenant Jimmy Asher, a soon-to-retire hands-off officer. When the money trail leads to major political figures, Sydnor worries about career damage but personally delivers a subpoena for financial records to State Senator Clay Davis. Davis's protests cause Mayor Clarence Royce to order Burrell to rein in the unit.

William Rawls suggests proper supervision, replacing Asher with Lieutenant Charles Marimow, a caustic commander known as a 'unit killer'. Marimow's style drives away Freamon and Greggs, leaving only Sydnor and Massey. Sydnor decides to leave at the first opening. With Herc and Kenneth Dozerman transferring in, Sydnor gains allies who share his dislike of Marimow.

The unit fails to build a case against Marlo under Marimow. Sydnor mentors Dozerman and warns Herc about lying to Marimow, but Herc continues acting unprofessionally. The unit is reconstituted under Freamon after Daniels becomes CID colonel. Asher is renamed Lieutenant, and Jimmy McNulty and Kima Greggs transfer back.

Dozerman stays while Herc is suspended pending an internal investigations division investigation. A new strategy is mapped against Marlo as the season ends. In season five, after over a year investigating the Stanfield Organization, the unit still lacks a strong case. Budget cuts close the unit, and Sydnor is disappointed to find his work wasted, realizing surveillance alone reduced crime.

Season five

Sydnor and Freamon are detailed to the State's Attorney's office to prepare the corruption case against Clay Davis. They prepare paperwork and assist Rhonda Pearlman in Grand Jury depositions. Sydnor uncovers evidence that Davis borrowed money from his mother for a mortgage deposit, a federal crime. Freamon sees this could mean a thirty-year jail term.

They present it to State's Attorney Rupert Bond, who refuses to take it federal for political reasons. In the series finale, Sydnor visits Judge Daniel Phelan in his chambers to apply back-channel pressure to advance an investigation, similar to McNulty in season one.