Because before, he'd already given Shiller a definite answer.
He initially thought it was just a whimsical question from Shiller, much like the countless other questions the professor had asked him before. All he needed was to think for a bit, give an answer, and the matter would be done.
His experience betrayed him. After Bruce gave his answer to Shiller, the professor whipped out a plan that was so meticulously crafted, absurd, and potentially highly effective as if it was off the end of a high-speed production line.
Bruce suddenly felt like he had been roped into a scheme against his will.
But he'd already promised Shiller. He always felt a certain unwillingness to lose face in front of Shiller, so he agreed to participate in the initial planning anyway.
The first step in the initial planning was to appoint a new mayor for Gotham as the previous one had died in a traffic accident. For some time, Gotham had been without a new mayor.
Generally speaking, appointing a new mayor for Gotham couldn't be done because no one was willing to risk their life here. Most of the time, it's Wayne Enterprises that pays to have someone come over. Among so many politicians, there would always be a few who were willing to risk death for money.
This time, however, Gotham had set its eyes on the former mayor of the City of Chicago. Just like Gotham, the two previous mayors of Chicago had also met tragic ends--one in a car accident and the other shot twice in the back, the resulting "suicide".
The former mayor was still alive because he was the head of Chicago's second largest mob, the Gospel Gang.
Shiller thought that such a curriculum vitae was quite appropriate for the mayor of Gotham. At the very least, he had managed traffic in Chicago quite well, after all, most drivers would give way when faced with a "Chicago typewriter".
So we arrive at the opening of the story where Bruce appears in Chicago and successfully woos the younger sister of the Gospel Gang's boss.
Of course, this was not the original plan. Batman certainly wouldn't come up with a plan that relies on womanizing to get to the target.
But the problem was, if Bruce wanted to accomplish this, he couldn't use his identity as Batman. After all, Batman was not that famous yet, he was only slightly well-known in Gotham, and had no jurisdiction over Chicago. So, of course, he would use his identity as the world's richest man, Bruce.
Playboy Bruce visiting a city would inevitably partake in some fun for a few days, otherwise, he would appear too committed to his work.
The moment word got out that the world's richest man was in town, every society event invited him. Bruce attended several parties in the space of two days, which included pretty much all of Chicago's social butterflies, including Tina Brown, the younger sister of Roy Brown.
She was extremely beautiful and a great dancer. With males being susceptible and females being attractive, the two quickly got together and things heated up.
With his arm around Tina's shoulder, Bruce said, " ... That's the thing, I really can't find a suitable candidate. Politicians don't last long in Gotham. I can't keep spending huge amounts of money for just a few months of peace, can I?"
Tina brushed her hair back and straddled Bruce, saying, "I'm beginning to wonder if you've come at this exact time on purpose. My brother's been encountering quite a bit of trouble recently. He's been looking for a place to hide."
"What happened to him? What could be troubling a boss of the Gospel Gang to such an extent?"
"Just a few days ago, in a mob war, a seven or eight-year-old boy was killed. Of course, he was a white boy, who was shot on his way home from school. The incident had a huge impact. If you've been reading the papers, you would know. Many places have sent in condemnations."
"The Gospel Gang wasn't involved in this incident. We are a branch of the Mafia after all, and we don't advocate fighting with guns all day. However, unluckily for us, this incident happened on our turf. Don't know which blind fool shot the bullet that far ..."
"My brother isn't afraid of the local mob, but the joint investigative group is troublesome. They're composed of senators from several states, each with different forces behind them. This isn't a problem that can be solved by a few gunshots ..."
"So, your brother wants to lie low?"
"Of course, if you're willing to spend some money to help my brother get out of this mess, the Brown family would be grateful," said Tina.
Bruce didn't mind her ulterior motives, he knew from the beginning that Tina came for him. After all, Bruce's own motives weren't entirely pure, this was nothing more than playing to the crowd.
"Have you thought it through? Being the mayor of Gotham isn't that easy."
Tina raised her eyebrows in surprise and said, "Don't you know? The famous godfather of the Falcone family in Gotham actually split from the Chicago Mafia, so we share common roots. My father has always been in contact with this godfather. After my father died, my brother even made a special trip to Gotham to pay respects to His Excellency Falcone."
"Of course, I also know that my brother cannot secure his position just by relying on these personal relationships. But if you stand by his side, things would be much easier."
Bruce didn't say anything, but he felt that the most important thing the future new mayor might have to rely on was that crazy plan of the professor.
The meeting with Roy took place on a clear morning in Gotham. He was a typical Chicago mob boss, wearing a trench coat, a cap, and carrying a violin case, which held the famous "Chicago typewriter".
The new mayor pleased Shiller immensely. Within the time it took to consume one cigarette, he fully grasped Shiller's intention for the Gotham Gang and the Chicago Mob to join hands in friendship and mutual development.