Walter "Pops" Holland is the Racket Boss of the smuggling racket in Tickfaw Harbor, running it for Frank Pagani. Back when he was younger, Pops used to joke he was descended from Blackbeard, and as proficient as he is at theft and smuggling, Donovan is inclined to believe him. 
Frank has Pops smuggling anything he can get his hands on between Tickfaw and Cuba -- electronics, cars, art, you name it -- and all of it goes down without a second look from either U.S. Customs or the Coast Guard. Since losing the warehouse in River Row, Pops has had to resort to air-drops to get the contraband in. He has his right-hand man Butterbean organizing the whole operation at the Coastal Patrol Marina north of Southdowns. Meanwhile, Jerry Verret keeps busy with his crew pulling cargo off of boxcars at a local train yard.
In 1968, Pops' racket was taken over by Lincoln Clay, who was working with inside information he received from Pablo Duarte. Lincoln damaged Pops' smuggling operation by killing Butterbean and cutting off his air-drop operation. He also took out Jerry Verret and destroyed Pops' shipments. Once everything fell apart, Pops was drawn out, giving Lincoln the opportunity to confront him. After successfully infiltrating Holland Bros. Shipping & Freight, Lincoln dealt with Pops and ended his association with the Marcano Crime Family.
- Junior Holland (son)
- Alice Holland (daughter)
- His daughter Alice works for Pops in the office.