The bar is an iconic symbol in Delray Hollow, which served as the home for the Robinson family and a base of operations for the Black Mob until February 1968. Sammy Robinson ran all of the mob's operations out of his office there and used it as a recruitment center for young black kids that he would take off the street to work for him in his rackets.  Lincoln Clay was one of these kids, and he soon became a member of the family when the Robinsons took him in as one of their own in 1958.
In February 1968, Sal Marcano double-crossed Sammy after a heist he helped pull off at the Federal Reserve. Marcano and his men killed Sammy, Ellis Robinson, Danny Burke, and left Lincoln Clay for dead. They then set the bar on fire, reducing the building to a burned-out shell. A botched investigation into the fire by local authorities falsely concluded that it had been the result of a gas leak.
In June of 1968, Lincoln's aunt Lily Robinson returned to New Bordeaux. Seeing the value in black-owned businesses in the Hollow, she convinced Lincoln to rebuild the bar as a testament to her late brother Sammy. With Lincoln providing the funds, and Lily coordinating the repairs, the two rebuilt the bar from top to bottom, investing over $185,000 into it.
Once the renovations are complete, they celebrate their success by hosting an opening celebration where Father James and most of Delray Hollow turn out to raise a glass in honor of Sammy Robinson. The renovated bar features a live jazz band, a fully staffed kitchen, an outdoor smoking patio, and a game room with billiards and darts. The exterior is updated with awnings and a mural of the Robinson family. Lincoln's basement living quarters are given a complete overhaul, and the bar even includes an office for himself upstairs.
Prior to 1968, Charles Laveau worked as a bartender at Sammy's.  After the renovations are complete, the bar employs a host of bartenders, waitresses, and kitchen staff. Lincoln brings in Oscar to work as a bouncer after he lost his job at Nuit Blanche. He hires Reggie as a bartender, and Lil Ernie and his jazz band play live music for the guests.
Sign of the Times
- Medicine Cabinet in the kitchen.
- Weapon Locker with a Tac-Vest in Lincoln's basement bedroom.
- A note on the plaque of Scott "Brass Balls" Morrow in the upstairs game room.
- After the renovation Lincoln is able to drink beer or bourbon at the bar or upstairs in his office.
- Despite being rebuilt in the mission Sammy's Renovation, the documentary footage of Father James pointing out where Sammy's used to be, stating that no one wanted to live there so they paved it over, will still play. It is unknown if this is an oversight or meant to imply that it was demolished for other unknown reasons prior to 2016.
- After purchasing Office Level 1, Lily Robinson will move upstairs to the office. If this happens before the fifth upgrade, Lincoln will be standing in the bar talking to the wall where Lily usually stands during Angry White Boys.
- After completing the renovations, trying to exit through the western door of Sammy's will show a short load screen, then spawn the player still inside the building. This happens most often if you try right after reloading.