Smith attends the reception Harry Daugherty throws at the beginning of the 1920 Republican Convention in Chicago, Illinois. He prevents Warren Harding's mistress from entering the room when she tries to see Harding because his wife Florence Harding is present. ("Hold Me in Paradise")
Smith remains an aide to Daugherty following Daugherty's appointment as Attorney General. Smith has no job title but receives a salary from the Department of Justice. Smith accompanies Daugherty on a visit to Atlantic City for memorial day 1921. Daugherty is purported to be there to represent President Harding's administration but has actually come to discuss saving his political ally Atlantic County Treasurer Nucky Thompson from charges of election fraud. Smith attends the ceremony for the beginning of construction on the Atlantic City war memorial. Later in the day he plays a round of golf with Daugherty and Thompson. Before their game Smith asks Thompson to provide a reference for him with Cincinnati bootlegger George Remus. Smith is planning to become involved in bootlegging with Remus. Smith assists Daugherty in selecting a prosecutor to help Thompson avoid conviction on charges of election fraud. Smith chooses Charles Kenneth Thorogood for this role. That night Daugherty, Smith and Thorogood enjoy a bawdy party with four prostitutes in Thompson's suite at the Ritz Carlton hotel. ("Gimcrack & Bunkum")
Smith meets with Remus and arranges to sell Remus licenses for the production of liquor for medicinal use. Daugherty passes on a thank you to Nucky from Smith regarding the introduction. Later, Smith announces that Senator Walter Edge has come to visit Daugherty. Edge leverages Daugherty into replacing Thorogood as Nucky's prosecutor using the threat of an investigation into the proposed Bureau of Veteran's Affairs. ("The Age of Reason")
Smith accompanies Harry Daugherty to a meeting with Nucky Thompson at the Ritz Carlton Hotel in Atlantic City. Nucky dismissively sends Smith to look at cigars with his assistant Eddie Kessler when the talk turns to real business. Nucky is concerned at the growing press interest in corruption within the Harding administration. Daugherty has employed a bag man to make his protection collections for him. ("Resolution")
A sub committee is started to investigate if the Bureau of Prohibition is being undermined by the Department of Justice. Smith unaware what they are investigating, fearing for the worst, has Gaston Means pay of Senator Edge's aid so he can relay the information to him. Means having received the information, tells Smith about what he has learned. Smith is panicking at the thought of being indicted for corruption. Means tries to calm him down by advising him to prosecute a premier bootlegger to deflect the criticism brought upon them. Smith however is terrified of trying to bring down the people they are in business with, fearing for his own future if that would happen.
The next month, Smith, attorney general Daugherty and investigator Means attends a conference with the Boy Scouts of America in which it becomes clear that Jess is having a nervous breakdown, not being able to cope with their corruption.
Later Nucky arrives in Washington heading directly to Daugherty's office, there he finds him in a meeting with George Remus and Smith. Smith and George leave the room and Nucky notes that Smith looks like he's "about to be burned to the stake"
A couple of months later Nucky is reading a newspaper saying "sources alleges Remus paid attorney general's aide" He then receives a phone call from Gaston Means which reports that Smith has manifested all signs of erratic behavior and that in his hysteria would be able to implicate Nucky to anyone asking him about his corruption. Nucky after thinking about it, agrees to have Jess Smith killed paying Means $40,000 for the job.
Means then visits Smith were he makes it clear to him that some money he has received from George Remus are marked and that they can be traced by the Treasury Department and if they are traced back to him he will be in trouble. Smith bursts out in panic saying that everything is over, Means however assures him that if he still has the money he can burn them(although this is only a play by means so he can assure Daugherty that Smith has to be liquidated) While Smith takes the money outside and burns it, Means brings this to Daugherty's attention and assures him that instead of caring for Smith he should instead try to save himself from going to jail. Means offers to have him killed and Harry agrees to pay $40,000 for the favor.
The same day Harry goes to see Smith were they share a reminiscing moment before Harry says his goodbye to him. The same evening Means goes to Smith's bedroom to have him murdered, However Smith being prepared for the worst emerges with a gun, pointing it at Means. Jess realizes Harry has paid him to murder him and he tears up completely before eventually committing suicide.
- Harry Daugherty - Friend and employer, Attorney General from March 1921 onwards
- Nucky Thompson - Political associate, former Atlantic County Treasurer
- George Remus - Bootlegging associate (arrested)
- Charles Kenneth Thorogood - Colleague, Assistant US Attorney
- Walter Edge - Political associate, State Senator for New Jersey
- Warren Harding - Political associate, President of the USA from December 1920 onwards
- Florence Harding - First Lady of the USA
- Nan Britton - Harding's mistress
Season 1: played by Daniel Cox
|Season one appearances|
|Boardwalk Empire||The Ivory Tower||Broadway Limited||Anastasia|
|Nights in Ballygran||Family Limitation||Home||Hold Me in Paradise|
|Belle Femme||The Emerald City||Paris Green||A Return to Normalcy|
Season 2 & 3: played by Ed Jewett
|Season two appearances|
|21||Ourselves Alone||A Dangerous Maid||What Does the Bee Do?|
|Gimcrack & Bunkum||The Age of Reason||Peg of Old||Two Boats and a Lifeguard|
|Battle of the Century||Georgia Peaches||Under God's Power She Flourishes||To the Lost|
|Season three appearances|
|"Resolution"||"Spaghetti and Coffee"||"Bone for Tuna"||"Blue Bell Boy"|
|"You'd Be Surprised"||"Ging Gang Goolie"||"Sunday Best"||"The Pony"|
|"The Milkmaid's Lot"||"A Man, A Plan..."||"Two Imposters"||"Margate Sands"|