I

THIRTY YEARS AGO

Roberto di Matteo could be described as many things, but he certainly was never one of life’s deep thinkers. If anything, he was always a binary type of guy. To him, things were either OK, or they were not OK. If they were OK, he was happy to go with the flow. If they were not OK, he tried to change his course.

During his time at Columbia Grammar School, things were predominantly OK. The work wasn’t too hard. He never stood out as a student, but he was never in danger of being asked to leave. There was plenty of time for the kinds of activities most suited to his abilities. Sleeping late. Playing cards. Drinking. Chasing girls. Playing video games, which had seemed super advanced back then but were laughably dated now.

Despite all the distractions, Roberto did just enough good work to get into Vassar. That was the version of history he liked, anyway. The rumor spread by some of his classmates said his admission had more to do with his mother being an alum, and a generous donation from his father, than his grades. But even if that was true, Roberto was OK with it.

At college, Roberto followed essentially the same path. Only there was more time for sleeping. More girls to chase. More beer to drink. Lots of other substances to experiment with. And video games that improved by the month. As long as you could foot the bill, which Roberto was able to do. Thanks to his father. And that was OK.

Roberto didn’t get down to any serious work until it was time to think about law school. He must have raised his game sufficiently, though, because he ended up getting admitted to Yale. There were more pesky rumors about his father’s donations, of course, but Roberto didn’t care. By now, his eyes were firmly on the prize. He was ready to knuckle down. To tick all the necessary boxes—his degree, the bar (albeit not the kind he was previously familiar with)—and grab his future with both hands. Because there was a place waiting for him at his father’s firm, in New York. It was a very prestigious firm: Suggett, Lyons, and Darracott.

At first, Roberto was OK with following in his father’s footsteps. He liked the firm’s fancy office on Lexington. The daily bagel delivery from H&H. The three- (or in his case, four- or five-) martini lunches with clients he was sometimes invited to sit in on. But when the initial gloss wore off, he found the going a lot more difficult than he’d expected. It turned out that his father being a partner made settling in harder, not easier. The other associates resented him. The other partners had high expectations, which left them frequently disappointed in him. He limped his way through one boring research assignment after another and made the occasional lackluster second chair appearance, hoping that if he could survive his first year, his prospects would somehow improve. He was wrong. His performance review on the anniversary of his hiring was harsh. And Roberto was not OK with that.

So he quit.

There were advantages to life as a solo operator, as Roberto soon found out. Sure, the office space he wound up with wasn’t quite as upmarket as the big firm’s. But what it lacked in polish and prestige, it gained in other ways. Like not having anyone in it who kept tabs on what time he arrived in the morning. What time he came back from lunch. If he came back. And when it came to hiring secretaries, he could apply his own set of criteria to the selection process. Criteria that weren’t exclusively related to administrative ability. Or to any kind of ability, for that matter.

The first couple of cases Roberto tried after hanging up his own shingle worked out surprisingly well. They didn’t draw him into deep legal waters, so they weren’t too hard for him to navigate. They didn’t take too long for him to wrap up, or require too much effort along the way. Those aspects were definitely OK. Less OK was the paltry amount of money they brought with them, but Roberto felt he shouldn’t complain. The cases had really just been bones that his father and his friends had been kind enough to throw, and Roberto didn’t want the source of such easy work to dry up. But regardless of his wishes, after a few months the flow of referrals had slowed to a trickle. Soon a full-on drought had set in. Faced with the prospect of having to slink back to his old man with his tail between his legs, Roberto was forced into an unpalatable realization. He was going to have to make his own rain, as they say in the legal profession. And that was not OK. He didn’t mind snow, as long as he was in Klosters or Cortina for the skiing. He enjoyed the sun, provided he was on the beach in Bora Bora or the Maldives. But as far as he could see, rain had no redeeming features. All it did was leave you damp and soggy. He’d never liked it. Not even the metaphorical kind.

Roberto had often heard it said that you could make your own luck. He’d always thought that sounded tedious, so was amazed to discover that all you had to do was postpone any thought of rainmaking until you’d completed the final level of The Legend of Zelda. He achieved that feat one Monday around lunchtime and had been about to head out for a quick slice of pizza and maybe a couple of Peronis when Samantha, his latest assistant, announced that he had a visitor. Before Roberto could respond with a suitable excuse to dodge the meeting, a guy came into his office. He was around six feet tall with gray hair buzzed so short his stubble looked sharp, like hundreds of minuscule daggers. He moved with no apparent effort and folded himself into Roberto’s visitor’s chair without waiting for an invitation.

The spiky-looking guy spoke with a pronounced foreign accent. At first Roberto thought it must be Russian, though it turned out to be Azerbaijani. After the guy left Roberto had to look the place up on a map. He didn’t have to think too long about the case the guy had offered him, though. It was to represent a friend of his. The guy made no bones about it, his friend was guilty. He wasn’t looking for an acquittal. Just reasonable bail, so that he could be present at his daughter’s wedding. That sounded straightforward enough. And the guy was paying cash, which was definitely OK.

As luck would have it, the ADA prosecuting the case was a friend of Roberto’s from law school. Roberto had a word in the ADA’s ear over a long, well-lubricated lunch. The ADA agreed to do Roberto a solid. Everyone was happy. Until the client skipped bail. He didn’t even show up to see his daughter walk down the aisle. Roberto was having a hard time deciding whether he was OK with that when the guy who’d hired him showed back up. He brought more cash with him. A lot more cash. It was a retainer, he said, for a new client. The kind who, if nurtured correctly—and Roberto wasn’t too naïve to understand what that meant—would leave Roberto never having to worry about making rain again.

And Roberto was most definitely OK with that.