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- During an interdepartmental street hockey game, Tommy starts to becomes suspicious that another company might be looking to poach "The Probie" from Ladder62. The potential issue weighs on Tommy because he realizes that while "The Probie" takes tons of abuse, he is still part of their family. Johnny's intense effort to go above and beyond for Janet and the girls leaves Janet ill at ease. Perhaps its because Tommy never took the same amount of time to dote on her, or maybe because she's not completely over him. The situation is complicated when Janet decides to pay a surprise visit to her ex. After an innocent mix up between ibuprofen and sleeping pills, Sean ends up sleepwalking and causing a brutally honest ruckus around the city. On the job, Lou makes a wrong turn that puts him and Franco in danger.
- The spotting of Jimmy's "ghost" is the talk of the firehouse. Colleen blames Tommy for her failed relationship, while Tommy figures out a way to fix his own. Franco and Natalie come to an understanding, while Lou, Mike and Latrina come to an understanding of their own. Tommy and his father take in a ballgame.
- Things are not going well for Tommy Gavin (Denis Leary). His wife Janet (Andrea Roth) has taken the kids, sold the house and left him. His girlfriend, Sheila (Callie Thorne), is pregnant. He is bored out of his mind at the Staten Island firehouse he has recently been assigned to. And his drinking is spiraling out of control. Tommy hits rock bottom and calls on his former crew mates from 62 Truck to try and help him get his life back on track.
- A meeting of the elders occurs with surprising results, Doc's absence is noted by Swearengen, Alma battles her addiction, and Sol offers Trixie something she never expected.
- After a bitter argument with Tommy over their living situation, Tommy's dad goes missing. Tommy is disgusted by Lou's latest love interest, while Sean and Maggie's disastrous meeting with the local priest threatens their future marriage. The new woman in Jerry's life puts him in danger.
- Tommy looks to his cousin Mickey, now an ex-priest, for help in understanding the bizarre visions he's been having since he quit drinking. When Lou allows a disagreement with Laura to escalate, the crew tries to help Laura understand the essence of male camaraderie. Tommy is put in harm's way during a fire when a miscommunication happens between Chief Reilly and Mike The Probie. Tommy's Dad is shocked when Teddy turns up in the last place he would ever expect.
- Tommy meets with Sheila in hopes of finding out what really happened on the night of the fire. Lou has his sights set on a new recruit who can really help the squad's basketball team. Teddy is released from prison. Tommy's daughter Colleen is believed to have run away from home.
- A dandy arrives by stage coach and immediately begins exploring how to bring culture to the camp, Alma and Hearst negotiate business, and Hearst's Aunt Lou comes to camp.
- The entire firehouse seems to be on edge. Lou continues to fall in a downward spiral as he avoids his home life and becomes more and more irritable, turning to alcohol to solve his problems. The Chief is still struggling to pay for his wife's nursing home, and tensions are high between Tommy and Sean who continues to try and hide his relationship with Tommy's sister. Franco has been sleeping with Alicia and realizes he is sitting on a gold mine when she spoils him and his daughter with generous gifts. "The Probie" seriously considers applying for a transfer, and fills out all the necessary paperwork; the issue is finding the courage to turn it in. When Tommy forgets to pick his children up from school, his estranged wife Janet, confronts him at the house and it is finally clear that their marriage is over.
- Death in the camp spooks the superstitious, and the impending funeral causes much sorrow. Cy is convinced that Andy - who will officiate at the service - is back in town to run a game. Wu asks Swearengen to back him against the "San Francisco cocksucker". Bullock encourages his wife to stay in Deadwood.
- Swearengen transforms the Gem into a courtroom as Deadwood is forced to make its own laws to try a cowardly murderer. With Calamity Jane off on a bender, Trixie is enlisted by Swearengen to help Alma with the orphaned child and to keep her pliable to his purposes. Fearing Andy's illness might threaten his business, Cy banishes him to the woods, where he is discovered by Jane.
- It's warrant sweep day at the Barn. Vic and the Strike Team discover visiting NBA superstar Derrick Tripp hanging out with his "homies" before the evening game with the Lakers. Vic decides to do his part for the home team by keeping Tripp as a "friendly hostage". One of Vic's street informants, Connie, approaches him after having been roughed up by a new john. Vic hands off the case to Claudette and Dutch, who is convinced they're on the trail of a serial killer. Dutch's theories are proved wrong when he and Claudette ultimately discover that their perp is not a serial killer but rather a disturbed man who is raping women in a desperate attempt to procreate. Danny and Julien stumble upon a gun smuggling ring while delivering one of their warrants and disaster is averted only by Danny's sharp instincts. David has his hands full overseeing the sweep, managing an increasingly packed cage, soothing the frazzled nerves of the attending desk sergeant, and avoiding a potential lawsuit from Derrick Tripp's lawyer over the disappearance of his star client.
- Story of how a group of incorruptible federal lawmen helped put 1920s' Chicago gangster Al Capone in prison.
- Another attack is made at Hearst's behest, Harry and Bullock travel to Sturgis for campaigning, and there's unrest in Langrishe's troupe.
- Elections are just days away, and Bullock lets his temper get away from him. Alma's pregnancy is not progressing as expected, and Swearengen baits Hearst.
- Election day arrives, Hearst has his revenge, Sol and Trixie have it out, and Tolliver releases rage at his impotence.
- Deadwood breathes easier when some riders arrive in town with the smallpox vaccine, and word of a possible treaty with the Sioux. The results of Bullock's analysis of her gold claim move Alma to reassess her plans and sets up a confrontation between Bullock and Swearengen. When Flora tries to quit, Cy teaches Joanie a deadly lesson at the expense of a couple of con artists.
- After tending to an overturned bus and saving the lives of multiple children, the Reverend Al Sharpton publicly denounces the FDNY for ignoring the needs of the black community by choosing to rescue the bus on the way to help a black man with chest pains. The station, and the entire community are responding in interesting ways. Sean confronts Tommy about his relationship with Maggie and Tommy warns him that his sister is trouble. Franco continues his relationship with Alicia, and Tommy and Sheila's relationship takes an interesting turn, especially when Tommy informs her that he will be making a deposit the next day, and not at a bank. Chief Reilly takes the job at the bar, and finds it difficult and tiring. The guys at the house take advantage of his vulnerability by playing practical jokes on him.
- Alma proposes opening a bank with the help of Sol Star. A new schoolteacher arrives in town, much to Merrick's delight. Much to Wu's dismay, new Chinese whores arrive. Wolcott's inner demons wreak havoc on Joanie's whorehouse, testing his alliance with Cy. Bullock attempts to keep order in the camp, and at the same time settle into family life.
- General Crook rolls into Deadwood with his troops, known as "Custer's avengers," and the Yankton magistrate, Clagett, prompting a parade and business solicitations from E.B. Farnum and Cy Tolliver. Al Swearengen delivers a tortured soul from suffering, and Bullock reacts decisively to Russell's intentions regarding Alma. Stapleton's new commission as sheriff proves short-lived, and Bullock and Alma have a late-night meeting.
- Tommy finds himself keeping vigil at the bedside of a young boy who was critically wounded in a fire. Chief Reilly learns a little more than he can handle about his gay son's relationship. Lou comes up with a plan to attract the attention of an old girlfriend.
- When a priest delivers some startling news, Tommy wonders if his Dad has been living a double life. Chief Jerry discovers just how far his wife's mind has slipped, and he is forced to ask for help from his estranged, gay son. When Laura files a complaint against Lou, the whole crew is ordered to undergo sensitivity training. Now that Colleen is home, Tommy comes up with a plan to get the rest of his kids back; meanwhile, Tommy starts to suspect that Sheila is hiding something from him.
- To make the next hockey game with the NYPD a wild affair, Tommy mends fences with his ex-co-captain, Ryan, who offers to enlist a fireman who is on leave for beating up three cops. As Lou's affair with Sondra heats up, and Mike comes to grips with Theresa's eating disorder, Franco counsels Sean on how to dump Carol, a woman he says is a bad kisser. And after another day at the track with Uncle Teddy and Arlo leaves him with plenty of cash for Janet and Sheila, Tommy is startled when Laura questions his motives and his sanity. Then, after she's the only one who can stop an angry man from attacking the firefighters removing his morbidly obese mother's corpse from her apartment, Laura gains some credibility with the crew.
- On a call, the guys convince Sean to ask out a girl who, unbeknownst to Garrity, is a transvestite. Meanwhile, Franco is feeling guilty about abandoning his daughter, and tries to find out where she was placed. As retribution for his attack, Tommy uses his City connections (his cousin) to have Roger arrested. Janet confronts Tommy and asks about the allegations Tommy is making against Roger. Tommy seems to have the upper hand, as he decides whether to press charges against Roger. Janet feels bad about the beating Tommy took from Roger's friends, until Tommy's bootie call unexpectedly shows up at his house and runs into Janet where introductions are not pleasant. Lou finally shares his poetry with people outside the firehouse and his home but their reactions aren't quite what he expected.
- Lou regrets participating in the FDNY bone marrow donation program when he meets the miserable person whose life he saved. Sean becomes suspicious of his new girlfriend when he discovers her habit of dating firemen. Franco's worsening painkiller addiction puts his daughter at risk. Tommy tries to learn the truth about Sheila's pregnancy, while executing a new plan to take his kids back.
- Tommy pays Janet a visit to discuss her pregnancy, which leads to an emotional confrontation with Johnny. Teddy finds his conjugal visits disappointing, while Franco tries to befriend his new girlfriend's mentally challenged brother. Tommy keeps vigil at the bedside of a severely injured firefighter.
- Doc contemplates a procedure that could cure Swearengen - or kill him. Bullock attempts to settle into domesticity, while Sol gets a new student bookkeeper - Trixie. Alma cuts ties with Sofia's tutor, Miss Isringhausen. Joanie and Maddie argue over the business. The County Commissioner's arrival spawns rumors about the camp's future and legal ownership of the gold claims.
- Competition arrives for Swearengen in the form of the Bella Union, a new gambling outfit from Chicago operated by savvy Cy Tolliver, Madame Joanie Stubbs and gaming guru Eddie Sawyer. Hickok puts up precious collateral in a poker game with McCall; Bullock and Sol strike a deal with Swearengen on a lot for their hardware store. Garret threatens Swearengen before investigating his gold claim.
- The firehouse learns of the Chief's suicide. Tommy agrees to buy things for his daughter Colleen in exchange for her keeping in contact. He and Janet decide to see a marriage counselor. Franco plans on proposing to Natalie. Garrity considers divorcing Maggie.
- Bullock encounters native resistance in his quest to bring a murderer to justice. Swearengen presses Farnum to keep tabs on Alma and Trixie. After an outbreak of smallpox hits Deadwood, the camp fathers pool their resources to track down the vaccine, and Doc enlists Jane as a nurse. Swearengen proudly collaborates on an article in the Deadwood Pioneer meant to minimize the threat of the outbreak.
- While Dutch and Claudette investigate the murder of Nancy Reborg, they discover that her daughter is missing and has been sold by her addict father to a child molester. David tries to crack corruption in the Barn by recruiting Terry to help him take down Vic.
- The crew encounters a little more than smoke when rescuing a man from his burning apartment. Sean (Steve Pasquale) runs into problems while asking Maggie's Dad (Charles Durning) for her hand in marriage. Tommy (Denis Leary) starts to realize that his crews future together may be in jeopardy. Johnny (Dean Winters) finally confronts Tommy face to face, and makes a difficult announcement.
- Tommy Gavin hopes that things start to return to normal now that his daughter Colleen has been discharged from the hospital. Unfortunately, still upset over their encounter in the emergency room, Roger makes matter worse when he accuses Tommy of being involved in the recent sabotage to his computer files and credit. Sean gets in over his head when Nez overdoses while the two are out at a bar. When Franco finds out what happened, he seems to be more concerned with Sean's disloyalty than the fact that he might have to care for a daughter he really doesn't know. Chief Jerry Reilly's suspension trial finally gets underway. The Chief is forced to contact his son, Peter, who may be his only chance to salvage his job. Three men, who are looking for revenge on Roger's behalf, confront Tommy.
- With annexation of Deadwood looming, Swearengen calls a meeting to set up an informal government. Bullock and Alma compare notes on Ellsworth and each other, and Farnum gets a special-delivery letter from Hickok and a special new post. Joanie finally prepares to make a go on her own, with Cy's avowed blessings, and after a long binge, Calamity Jane decides to ride out of town.
- Francis Wolcott, chief scout for a powerful mining operation, arrives to shake up the status quo - beginning with Cy Tolliver. Swearengen's lackeys fret as he refuses visitors and medical attention. Joanie's new partner, Maddie, reveals she's also running a game as their new brothel, the Chez Ami, services its first customer.
- A series of mail bombs target three wealthy siblings, but Monk thinks one of the brothers is actually responsible. The problem is, he's been in a coma for the last four months.
- The department flies into action after one of their own is poisoned by a secret Santa gift at their very own Christmas party.
- When Monk's favorite singer, Willie Nelson, is suspected of murdering his tour manager, Monk steps in to clear his name.
- When a woman drives off the road to her death, her body is mysteriously found three mornings later by a psychic known for fudging the truth. Monk must discover if she's telling the truth this time, or else let a murderer go free.
- A very tidy woman who resembles Trudy turns Monk's head while he's investigating a triple homicide. The only problem is, she's the prime suspect.
- Law student Julie Parlow's grandmother is kidnapped and held for ransom. But they don't have any money, so why did the kidnappers release her? And why did they feed her pizza?
- A woman is murdered during the San Francisco marathon and Monk suspects her married lover. But he was running the race, and his tracking chip says he never left.
- A sniper causes a car accident that nearly kills Stottlemeyer's wife, Karen. Now it's up to Monk to solve the case and keep Stottlemeyer from doing something he might regret.
- When billionaire software magnate Sidney Teal is shot dead by ex-cop Archie Modine after allegedly turning mugger and another policeman mysteriously flees the scene, Stottlemeyer calls in Monk to investigate. Not only is the idea of a billionaire turning mugger hard to swallow, the circumstances of the mugging are suspicious. Why, for example, would a mugger wear knee and elbow pads? Meanwhile, Sharona threatens to quit (this time for sure) when her paycheck bounces, and Stottlemeyer is hounded by reporters demanding information on "Fraidy Cop." Unable to continue the investigation without Sharona's help, Monk returns to the seemingly unsolvable mystery of his wife's murder only to find that his "new" clue isn't new; he's already talked to writer Kelly Street three times. Sharona finds that selling lamps isn't nearly as much fun as working for Monk (with or without money) and comes to the rescue with a new clue involving Teal and Modine.
- Monk's first flight proves to be harder than he anticipated when he begins to suspect that a fellow passenger murdered his wife.
- While on vacation at a resort, Benjy claims he witnessed a murder. Monk believes him, but with no body and the cleanest crime scene Monk has ever seen, it's going to be hard to convince everybody else.
- A judge is murdered while placing a 911 call, but before she dies she names her attacker - notorious criminal Dale Biederbeck. The problem is, "Dale the Whale" is over 800 pounds and hasn't left his bed in years.
- Monk attends a popular new play starring Sharona's sister Gail. But when Gail appears to stab and kill her costar during the live performance, Sharona calls Monk in to investigate.
- When a ringmaster is murdered by an acrobat in a crowded restaurant, Monk suspects his ex wife is responsible. But with her foot broken and in a cast, how could she have done it?
- When a powerful CEO and his wife are shot to death in a deserted parking lot, the police investigate the husband's enemies. But Monk thinks it's all about the wife and the affair she was having with a handsome young ballplayer.