|Season 5, Episode 14|
|Air date||November 10, 2011|
|Written by|| Ben Watkins|
|Directed by||Renny Harlin|
Damned If You Do
- Clients: Ricky Watson
- Bad Guys: Dion Carver
When the life of one of Michael's childhood friends is taken by gang warfare, things get personal as he decides to team up with the victim's brother to entrap the gang in a weapons scheme.
Michael finally has top secret clearance and Ansen wants him to use it to clear his name of all CIA databases. At the same time, Fiona wants to go after Ansen. She runs through traffic and dives under his car to plant a tracking device there.
Madeline delivers the bad news to Michael that his childhood friend, Andre, has been murdered. He had been the leader of a gang called the Magic City Overlords and had just been released from prison prior to the homicide. Andre's friend Dolly claims to have witnessed the new Overlords leader, Dion, murder Andre.
Michael and Jessie pose as weapons dealers to get a meeting with Dion and bring him down. Dolly gets dead shortly thereafter, but the weapons deal remains on. Elsewhere, Fiona and Sam plot entry into Ansen's apartment. So Sam poses as an environmental attorney to gain access.
Upset that Dolly has been killed, Ricky plants a bomb at Overlords HQ. Luckily, it doesn't go off until after Michael and Dion leave the building. Ricky puts Dion in a tough spot, fess up to the murders of Andre and Dolly and go to jail or suffer death by his gang.
Fiona and Sam get into Ansen's and find a high-tech satellite. Sam thinks he can use the lead. With Andre's case wrapped up, Michael heads to the CIA office to take care of Ansen's records.
- Jeffrey Donovan as Michael Westen
- Gabrielle Anwar as Fiona Glenanne
- Bruce Campbell as Sam Axe
- Coby Bell as Jesse Porter
- Sharon Gless as Madeline Westen
- Andre Holland as Dion Carver
- Indigo as Dolly
- Justin Smith as Blake
|Episodes | Season 5|
|Company Man • Bloodlines • Mind Games • No Good Deed • Square One • Enemy of My Enemy • Beseiged • Hard Out • Eye For an Eye • Army of One • Better Halves • Dead to Rights • Damned If You Do • Breaking Point • Necessary Evil • Depth Perception • Acceptable Loss • Fail Safe|