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When Speaker Donatello's critical condition makes Tommy the heir apparent for the Speakership of the House, Freddie Cork maneuvers to get on Tommy's good side. With the Italian mob, the Rhode Island Police, and the Feds after him, Michael’s obsessive need to find Colin puts everyone in jeopardy

Kath and Colin worry about what Michael might be capable of if he becomes too suspicious of their relationship. Eileen goes stir crazy when her advanced pregnancy confines her to bed. Tommy asks for Michael's help as the investigation hones in on the Waterfront Project.

Eileen worries that her family will never leave The Hill when Speaker Donatello draws Tommy back in to help pass the budget. Declan gets new information about Tommy's involvement in the Waterfront Project and breaks some rules to find a link between Tommy and Nozzoli. Rose's attachment to Colin fuels Michael's anger and paranoia as he refuses to help Nozzoli get in on Tommy's Waterfront contracts.

Declan's investigation triggers alarms among the corrupt politicians so Tommy tries to finesse information from the investigation. Rose receives a diagnosis and shares the truth with Ellen. Michael and Colin begin to clash as they help Freddie plan a robbery.

The Labor Day holiday weekend finds Michael increasingly paranoid and edgy; Tommy proposes a radical lifestyle change to Eileen; Declan and Cassie's getaway highlights the growing problems in their rocky marriage.

A tenement fire that kills several Latino squatters and a firefighter causes political fallout for Tommy. Colin begins drinking heavily because of a love triangle. Declan's investigation bears fruit and is expanded.

Tommy uses his new leverage to convince Mayor Panzarella to get behind the Waterfront development. At the same time, Michael's business dealings with Nozzoli create a new roadblock for Tommy. As Declan starts his investigation into state house corruption, Franklin's sudden disappearance draws attention. Eileen gets passed over at work because of her pregnancy as Rose tries to get answers about her mysterious illness.

Tommy's frustration with his new role as Speaker Donatello's errand boy leads him to consider a risky career change. With Michael still refusing to speak to Tommy, Colin arranges for both brothers to attend Rose's birthday party. Rose tries to hide her deteriorating health. Eileen struggles to meet the demands of her growing family while becoming more invested in her job at Social Services. Michael's relationship with Attorney General Franklin starts to unravel when Michael hears that Freddie Cork is getting bail. To avoid serious outside scrutiny, Tommy asks Declan to run a special investigation into corruption in the state house. Declan accepts, looking for real justice.

Freddie asks Nozzoli to kill Michael while Franklin investigates the outcome of the holiday furlough. Tommy makes a bid for the Speaker's chair. The death of a loved one brings Colin and Rose closer. Eileen finally puts her foot down when Dana Chase calls the Caffee house.

Some important information may lead to a holiday furlough from prison for Freddie Cork and Marty Trio. A frustrated Rose leaves for home on Thanksgiving morning, leaving the remaining Caffees to fend for themselves.

Declan is surprised by his new assignment he receives as a reward for joining the FBI. Eileen gets a shock when she volunteers at social services. Tommy is being pressured as a replacement for Judd. Colin and Michael form a partnership with Nozzoli.

It's election day on the Hill, and when early exit polls show Tommy running behind he pulls out all stops and engages in some down-and-dirty politics. Also, Michael “escorts” a hitman on a job as a favor to an Italian mobster, and Colin takes Kath to an abortion clinic.

Michael makes a move to seize more power as he and Kath await an addition to the family. Meanwhile, Tommy attempts to clean up the hill's bad section, Eileen bonds with some of the local politicians wives and Rose tries to deal with aging.

Tommy's trusted support system goes AWOL when he becomes plagued by personal and professional problems; Colin searches for his father; Michael contemplates a change in his lifestyle; Freddie leans on Declan to learn the whereabouts of a missing business associate.

Rose sows unrest between her sons which leads Michael to throw a wrench into Tommy's big real estate deal. Freddie asks Declan to use the police badge to negotiate with the competition. Eileen and Kath Perry find some common ground as they try to cover up Mary Rose’s delinquent behavior. Tommy and Dana Chase see more of each other.

Colin helps Michael and Eileen cope with the unexpected death of a friend while Freddie tries to avoid a war with the Italians; Tommy helps smooth things over with the Speaker of the House's mistress.

As Tommy begins his reelection campaign, he turns to his sister, Mary-Kate, rather than Eileen for support; Colin Carr, Tommy and Michael's estranged Irish cousin whom Rose deeply distrusts, returns to Providence.

In episode 201, the second season premiere, Tommy outmaneuvers a U.S. attorney as he and Eileen keep up the appearance of a happy marriage; Michael tries to reestablish his memory and his territory.

Michael is targeted for a hit; Marty Trio wears a wire to get evidence against Freddie; a double-dealing U.S. attorney aims to nail both Tommy and Michael; Declan suspects his partner is dirty; party boss Judson Fitzgerald shows signs of slipping; and Eileen parties with some old friends.

The ne'er-do-well Caffee patriarch turns up. He's in a financial jam and threatens to sell Rose's house unless Tommy and Michael help him clear up his $200,000 debt. Meanwhile, Pete falls off the wagon again and gets help from Eileen; Rose's friends turn their backs on her and turn their noses up at Michael's criminal activities; and Tommy finds out that Mary Rose has been working at Michael's liquor store.

A suicidal jump from a highway overpass causes a bus crash that kills passengers returning to the Hill from a New England Patriots game. Michael discovers a surprising secret about the leaper's identity and uses it to manipulate his boss, mobster Freddie Cork.

Rose plans a surprise birthday party for Michael while he's in New Jersey with an old girlfriend doing a job for Freddie; Tommy plays dirty politics in a bid to become Majority Leader; Eileen takes a step toward banishing her demons, but the pressure starts to get to her.

Despite his misgivings, Tommy teams with Michael to save a rundown local movie palace; Pete falls off the wagon, but gets help getting back on; Eileen confides her transgressions to Mary Kate; Rose gets a job and immediately makes noises about unionizing her co-workers; corrupt union boss Marty Trio reveals a secret to Declan.

Michael does an unexpected favor for Declan's cop partner; Tommy sees a lucrative reward for helping a black minister with a zoning problem; Michael catches Mary Rose smoking some Mary Jane with her school friends; Eileen's nocturnal wanderings lead her to a run-in with the cops.

The governor wants Tommy to introduce a bill that would tear down houses on the Hill and gain some jobs, and Tommy sees a chance to make some money out of the deal; Michael faces off with Armenian drug dealers who have set up shop in a neighborhood bar, and makes his lawyer brother-in-law Jimmy an offer he can't refuse; Rose takes a stand when her employer wants to lay off 25 workers at the mill.

Rose's regular Sunday family dinner is interrupted by gun-wielding Treasury agents on the trail of counterfeit currency that is being passed around town; Michael, who doesn't “point out rats, I stomp on 'em,” takes care of the guy who ratted him out to the Feds; Tommy seeks the Speaker's help on a bill that would be beneficial to a real-estate deal he is preparing.

A garbageman strike is stinking up the city and it looks like Tommy may have to get down and dirty with the party political machine to help reach a settlement; Michael tries to recruit members for his new crew; Eileen's lover misses their afternoon rendezvous.

In an attempt to take over a neighborhood store, Michael leans on a merchant by playing a game of Russian roulette with her mentally challenged brother; Tommy wheels and deals behind the scenes to keep a highway spur from bisecting the Hill; Eileen gets disturbing news during a doctor's visit.

State representative Tommy Caffee ends up getting blackmailed for government contracts by the local mob boss right after his brother Michael returns to Providence after being on the run from the law for 7 years.