Question: What date did Frank Grillo's Marvel supervillan first appear in comics?

Context paragraphs:
Captain America: The Winter Soldier: Captain America: The Winter Soldier is a 2014 American superhero film based on the Marvel Comics character Captain America, produced by Marvel Studios and distributed by Walt Disney Studios Motion Pictures.  It is the sequel to 2011's "" and the ninth film in the Marvel Cinematic Universe (MCU).  The film was directed by Anthony and Joe Russo, with a screenplay by Christopher Markus & Stephen McFeely, who had also written "The First Avenger".  It stars Chris Evans as Captain America, leading an ensemble cast that includes Scarlett Johansson, Sebastian Stan, Anthony Mackie, Cobie Smulders, Frank Grillo, Emily VanCamp, Hayley Atwell, Robert Redford, and Samuel L. Jackson.  In "Captain America: The Winter Soldier", Captain America, Black Widow, and Falcon join forces to uncover a conspiracy within S.H.I.E.L.D. while facing a mysterious assassin known as the Winter Soldier.

List of Waterloo Road characters (series 4): The following is a list of characters who first appear in the fourth series of the BBC school drama "Waterloo Road", in order of first appearance.  The fourth series consists of twenty episodes, first broadcast from 17 January to 20 May 2009.  The main cast remains mostly unchanged from series 3, augmented by Rob Cleaver in the first ten episodes and returning character Kim Campbell from episode eleven.  The Kelly family, consisting of mother Rose and her children Marley, Earl, Sambuca and Denzil, all first appear in episode 1.  Head Girl Flick Mellor and her father Ralph, head of the board of governors and local police chief, also debut in episode 1, as does head of extended services, and sister to head teacher Rachel Mason, Melissa Ryan.  Melissa's son Phillip and security guard Dave Miller first appear in episode two, and pupil Lauren Fletcher (later Lauren Andrews) makes her first appearance in episode six.

Pandemic (comics): Pandemic (Richard Palance) is a fictional supervillan in Marvel Comics who was first mentioned in "X-Men" vol.  2 #188 (2006) and appeared in "X-Men" vol.  2 #194 (2007).  He was created by Mike Carey and Humberto Ramos.

Frank Grillo: Frank Anthony Grillo (born June 8, 1965) is an American actor known for his roles in films such as "Warrior" (2011), "The Grey" (2012), "End of Watch" (2012) and "Zero Dark Thirty" (2012).  He had his first leading role in the action horror film "" (2014), portraying Sergeant Leo Barnes, a role he reprised in "" (2016).  He also plays the Marvel supervillain Brock Rumlow / Crossbones in the Marvel Cinematic Universe, and Big Daddy in the Chinese action film "Wolf Warriors 2" (2017), the highest-grossing non-Hollywood film of all time.

The Purge: Anarchy: The Purge: Anarchy is a 2014 American dystopian action horror film written and directed by James DeMonaco.  The film stars Frank Grillo, Carmen Ejogo, Zach Gilford, Kiele Sanchez, Zoë Soul and Michael K. Williams, with Edwin Hodge as the only actor to reprise his role from the first film.  It was released worldwide on July 18, 2014.  It is the sequel to 2013's "The Purge" and is the second installment in "The Purge" franchise.

Afro-Cuban jazz: Afro-Cuban jazz is the earliest form of Latin jazz.  It mixes Afro-Cuban clave-based rhythms with jazz harmonies and techniques of improvisation.  Afro-Cuban jazz first emerged in the early 1940s with the Cuban musicians Mario Bauza and Frank Grillo "Machito" in the band Machito and his Afro-Cubans, based in New York City.  In 1947 the collaborations of bebop innovator Dizzy Gillespie with Cuban percussionist Chano Pozo brought Afro-Cuban rhythms and instruments, most notably the tumbadora and the bongo, into the East Coast jazz scene.  Early combinations of jazz with Cuban music, such as Dizzy's and Pozo's "Manteca" and Charlie Parker's and Machito's "Mangó Mangüé", were commonly referred to as "Cubop", short for Cuban bebop.  During its first decades, the Afro-Cuban jazz movement was stronger in the United States than in Cuba itself.  In the early 1970s, the Orquesta Cubana de Música Moderna and later Irakere brought Afro-Cuban jazz into the Cuban music scene, influencing new styles such as songo.

Crossbones (comics): Crossbones (Brock Rumlow) is a fictional supervillain appearing in American comic books published by Marvel Comics, usually depicted as an adversary of the superhero Captain America.  Created by writer Mark Gruenwald and artist Kieron Dwyer, the character first appeared in "Captain America" #359 (October 1989).  Crossbones usually appears as an ally of the Red Skull.  He carried out the assassination of Captain America, although a hypnotized Sharon Carter is believed to have fired the fatal shots.

Captain America: Civil War: Captain America: Civil War is a 2016 American superhero film based on the Marvel Comics character Captain America, produced by Marvel Studios and distributed by Walt Disney Studios Motion Pictures.  It is the sequel to 2011's "" and 2014's "", and the thirteenth film of the Marvel Cinematic Universe (MCU).  The film is directed by Anthony and Joe Russo, with a screenplay by Christopher Markus & Stephen McFeely, and features an ensemble cast, including Chris Evans, Robert Downey Jr., Scarlett Johansson, Sebastian Stan, Anthony Mackie, Don Cheadle, Jeremy Renner, Chadwick Boseman, Paul Bettany, Elizabeth Olsen, Paul Rudd, Emily VanCamp, Tom Holland, Frank Grillo, William Hurt, and Daniel Brühl.  In "Captain America: Civil War", disagreement over international oversight of the Avengers fractures them into opposing factions—one led by Steve Rogers and the other by Tony Stark.

Crusaders (Marvel Comics): The Crusaders is a group of fictional characters appearing in American comic books published by Marvel Comics.  The characters first appear in "The Invaders" #14 (March 1977) and were created by Roy Thomas, Jack Kirby, and Frank Robbins.

Guardians of the Galaxy (1969 team): The original Guardians of the Galaxy are a superhero team appearing in American comic books published by Marvel Comics.  The Guardians first appear in "Marvel Super-Heroes" #18 (Jan. 1969).

Supporting paragraphs: Frank Grillo Crossbones (comics)
Answer: October 1989