In the Arrowverse, Freeland crime boss Tobias Whale finally met his demise at the hands of his nemesis Jefferson Pierce, aka Black Lightning, in the series finale that aired on May 2021. The killing was accidental since Jefferson often had a no-kill policy like Bruce Wayne. Tobias' relationship with Jefferson was also quite similar to that between Bruce Wayne and the Joker.
While the two often made each other's lives miserable, they had great respect for each other. This prevented them from harming each other whenever they had the opportunity. Despite his penchant for violence, what made Tobias a great villain was his intelligence. Black Lightning's primary antagonist never had a shortage of schemes up his sleeve.
10 Making Khalil His Henchman
Khalil was badly injured during the attempted assassination on Reverend Jeremiah Holt, but the sly Tobias visited him in hospital and in typical baddie fashion, he somehow convinced the teenager that it was all Jefferson Pierce's fault. He then promised to make him walk again, which he did.
Working with the A.S.A. Martin Proctor, Tobias provided the Garfield High student with a makeshift metal spinal cord that also gave him additional strength and durability. Thinking that Jefferson was the oppressor, Khalil began working for Tobias. He became Tobias Whale's most effective weapon, acquiring the name Painkiller.
9 Using The Freeland Police To Fight Jennifer
As the mayor, Tobias pumped up his efforts to get rid of all good metahumans. He targeted Jennifer, knowing she was the future because her powers were even better than those of her father. Aware that new Police Chief Ana Lopez considered metahumans to be enemies of Freeland too, he presented her a series of meta boosters to give to her police force and make them hunt Jennifer.
In a perfect act of persuasion, Tobias told Ana: "You only have guns because the bad guy have them, why not get powers[...'?" Not only did Ana take the serum herself but she also gave it to some of her trusted juniors like Detective Hassan Shakur. Were it not for Jefferson's intervention, Freeland's police officers would have achieved their missions.
8 Apologizing To Lady Eve For Lala's Murder Of Lawanda White
Before the events of the series, Tobias thought he had killed Jefferson Pierce, even going as far as to dump his body in a river. However, at the start of the series, rumors began surfacing that Jefferson Pierce had appeared. Tobias wasn't so sure but he got to find out by making up with Lady Eve. The Blackbird Funeral Parlor owner took offense when Lala killed Lawanda White.
Tobias apologized to Eve by giving her money and in return, Eve let her know about Reverend Jeremiah Holt's protest against the 100. While attempting to assassinate the reverend, Black Lighting appeared, and thus, Tobias was able to confirm that the hero that had been presumed dead was indeed alive.
7 Taking The Anti-Aging Serum
Black Lightning finally killed Tobias in the series finale and audiences saw the villain turned into an old man as life left his body. It was the end of a long and chaotic era, but Tobias wouldn't have caused havoc for so long if it wasn't for the anti-aging serum.
The serum — which was created by Dr. Helga Jace — boosted Tobias's strength and also prevented him from aging. In the same manner that Bane took Venom in the DC comics. Tobias' reliance on the anti-aging serum made him remain young and durable. As a result, his stint as a villain was a productive one.
6 Implanting Carbon-Fiber Body Armor In Syonide's Skin
There was no one Tobias wouldn't use for his own benefit — not even his own family members. In 1998, Tobias took Syonide from an orphanage and raised her like she was his own daughter. He trained her to become an assassin, going as far as to have carbon-fiber body armor implanted in her body.
This was a game-changer, as Syonide grew to become one of the most formidable assassins in America. She was able to withstand all kinds of attacks, including lightning blasts from Jefferson Pierce and power strikes by Annissa Pierce. Bullets also kept bouncing off her body. Thanks to this ability, Syonide was able to perform many high-profile missions for Tobias.
5 Convincing Lynn To Help Him Escape
Led by Agent Odell, the A.S.A terrorized everyone in Freeland in Season 3. Even the intelligent Tobias was held captive inside the A.S.A facilities, and as a result, he was temporarily relegated to a secondary antagonist.
Jefferson's wife, Dr. Lynn Stewart, was also forced to work for the A.S.A and as she interacted with Tobias on a frequent basis, he managed to get into her head. Despite what he had done to her family before, Tobias convinced her that the A.S.A was the enemy. She thus helped him escape by giving him the meta booster, which made him become invisible.
4 Putting Measures In Place To Protect Himself From Jefferson's Lightning Strikes
From the time Jefferson first appeared, Tobias knew he'd face off against the star metahuman a couple of times. Knowing that Jefferson's greatest weapon was his lightning strike, Tobias made plans to protect himself from it. First, he got an electric-proof undersuit, which helped him during his showdown with Jefferson at Garfield High School.
Tobias later had his serum updated so that his skin could resist lightning strikes from Jefferson. This proved beneficial during his final battle in the series finale. Jefferson's strikes could only push him away, not harm him. It took getting impaled on a giant spike for Tobias to finally die.
3 Wiring Money To Todd Green's Account To Persuade Him
Freeland child prodigy Todd Green graduated from college at 17 and earned his PhD at 21. He began working at a local research center but became disgruntled when the board denied him a research grant and gave it to the son of a wealthy industrialist who had funded the construction of a new wing.
Aware of Todd's intelligence, Tobias approached him and made him an offer. Todd was skeptical due to the villain's reputation. To prevent him from saying no, Tobias wired $100,000 to his account. Todd eventually accepted and began doing high-profile tech work for Tobias, including spying on the A.S.A's pods.
2 Convincing The People Of Freeland That He Had Their Best Interests At Heart
Mayor Billy Black appeared reluctant to work with Tobias, so the villain had him killed by Red. The murder happened during a press conference attack by the 100, hence it was never linked to Tobias.
Shortly after Billy's death, Tobias announced that he was running for mayor. Despite his questionable profile, Tobias managed to convince the residents that he was clean and that everything that had been said about him was wrong. He then won the race, making him able to control almost everything in Freeland.
1 Getting Giselle Cutter To Deal With Khalil
As expected, Khalil got to know the real Tobias and stopped working for him. This was a problem for Tobias because Khalil was deadly. Despite the fact that he had a tracker inside Khalil, Tobias tasked his former lover Giselle Cutter with hunting Khalil down. He had a simple explanation for it: he wanted to be a respectable citizen, hence he didn't want any dirt on his hands.
Settling on Giselle was a good decision as she was the only person capable of handling Khalil. She was a skilled markswoman, showing expertise in throwing poisoned knives. She also had the power of telekinesis. Giselle finally delivered Khalil to Tobias. For his disobedience, Khalil's spine was ripped off.
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