Tony Angelo

Tony Angelo was a ruthless crime lord that operated in City 17 after the fall of the Combine Empire. He was a minor antagonist during the "Mob arc" and the primary antagonist of the "New Combine arc" of City 17 Street. He is the overall quinary antagonist in the series, following The G-Man, Mr. Blackstone, Wallace Breen and Derrick Thompson.

Rise
After the fall of the Combine in 2007/08, Tony Angelo was one of three crime figures to start their own families, the others being Mr. Gelatray and Darko Rascalov. Tony was the most feared and ruthless out of the 3 men and although a good strategist, he was very aggressive and violent and lacked any morals.

Hiring Nathan Johnson
"The name is Tony. Fat Tony to you."

- Tony to Nathan.

In March 2010 Tony hired Nathan Johnson to work for his family as an enforcer, having learned of Nathan's previous skills. But three-months later, Tony received a call from Nathan's enemy Frank Blackstone that Nathan was planning to betray him (which was untrue). Paranoid, Tony lured Nathan to his office block and attempted to shoot him dead. Although Nathan had been shot, he got the upper hand and severally wounded Tony, presumably killing him.

After this Nathan went on the run after "killing" Tony. Tony's Underboss Don Simmons (and Nathan's friend) took over the Angelo crime family, and pardoned Nathan for Tony's demise. Despite being presumed dead, Tony was in fact alive and took on a new identity and left City 17.

Establishing the New Combine Empire
Tony plotted to found a New Combine Empire. Taking on a new identity and running his own taxi business, he began smuggling drugs and weapons to fund his new scheme. He also set up child factories across City 17, City 18 and City 19 and used them to make cremators and weapons for Tony's army. Tony also hired a former Metrocop named Erik to act as his proxy and the face of the New Combine, in order to distant any ties to Tony himself.

When Tony was unmasked, he attempted to cover up his crimes by destroying one of his child factories (with the workers still inside) but Nathan was the one who prevented it and rescued them. Nathan discovered Tony was in fact still alive, but all was too late as Tony fled once again.

The Combine Civil War
During the New Combine Civil War Nathan ended up allying himself with the New Combine, hoping to use them to track Tony down (unaware Tony was pulling their strings). Nathan however had a change of heart and sided with the Resistance, but the New Combine won and took over City 17.

Planned domination of Europe
Tony and the New Combine planned a major war with the Resistance government that were spread across Eastern Europe. Andy Shephard infiltrated Tony's operation. But Tony found out Andy was undercover and had him killed.

Arrest
A few months into the European Conflict, Tony was exposed as being the ruler of the New Combine. While attacking City 17, he attempted to escape once again by train but Nathan and Pyro chased it down and derailed the train. Nathan was tempted to murder Tony, but allowed him to be taken into police custody. The New Combine merged with the Resistance Government and came to peace, and Tony was locked away with a life sentence looming over his head.

Revenge scheme and death
Two-months since his arrest, Tony managed to escape prison. He kidnapped Nathan's sister and held her hostage at the Johnson household. Nathan arrived back and after a stand-off, Tony shot her in the head, killing her. In turn, Nathan shot Tony multiple times, killing him.

Trivia

 * Tony's demise is similar to that of Mr. Green. Both men held somebody close to Nathan in his apartment and waited to kill him. However unlike Mr. Green, Tony managed to shoot and kill his captive before Nathan could finish him off.