Table-top tennis and under-the-table cash with Oliver

I learned a lot about money laundering and cybercrime on my last portrait assignment.

“The scope is so large now,” my subject told me. “It’s a tougher market. It’s more exciting. It’s constantly evolving.”

And Oliver Wood hopes to be a part of a force that stops it.

Oliver, 23, is a recent graduate of Clemson University’s business school, and hired me to give him some head-shots for his resume. His degree is in finance management, a field that remains as button-down boring as you want to make it — but as he pointed out to me, one side of that industry is evolving into something feral. Oliver aspires to help not just clients, but whole countries in the battle against the trillion-dollar money-laundering underground.

“You’re dealing with different cultures,” he told me. “It’s an opportunity to become more involved with other places.”

Oliver grew up competitive: as a high school tennis player, he contributed to four Illinois championship teams. He also grew up comfortable with pursuits that do not fascinate the general public — he helped create a table-tennis team at his high school.

“It’s always a conversation-starter,” he said.

And while money fascinates everyone, Oliver laments that so many people have so little interest in learning how to protect and multiply it. There are no profound complexities to the basics of financial management, he said:

• Savings accounts are crucial, and the younger you set one up for your kids, the more likely they become to live as financially responsible adults.

• Keep your receipts and watch your expenses, then set a budget to determine where your money should go instead where it just happens to end up going. The worst excuse, he said, is to tell yourself that you don’t need a budget because you don’t make enough money.

“I think it should be taught more in schools,” he said. “You should go through life with a financial perspective.”

Of course, there are a multitude of financial perspectives for any individual to take, including the shady and the criminal. So many computers hold so many debit card numbers, credit card numbers, Social Security numbers and on and on — and that says nothing about the illicit movement of old-fashioned paper money. Multi-national plots have never been harder to foil, he says.

It is a scene Oliver hopes to work his way into.

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This is not a joke: will Patty marry Ray?

On the night of his 26th birthday, Ray knelt down before the love of his life — empty-handed. He was a Chicago Public Schools teacher, and he knew that he would be able to afford a ring for Patty someday…but he could not wait another night to ask for her hand.

But with no ring, Patty thought Ray was joking. So he asked her again.

And she thought he was kidding, again. As Ray tells the story, this question-and-laughter went on for a few rounds.

Ray is a blogger, a writer published in magazines and read on radio, an aspiring novelist and a public speaker. I met him through his appearances on Chicago’s storytelling circuits, where his fables of students can be both hilarious and grievous in the same speech. After my session with his family, he unspooled a special tale just for me: how he won Patty’s heart, her mind and (after a few tries) her hand.

Ray and Patty were promising young educators who studied under the same professor; in 1997, they were both invited to speak at a conference in Sacramento, on a panel about culturally relevant teaching. Both were thrilled to be part of a panel...neither expected much from the other.

“We knew of each other,” Ray told me. “To be honest, we weren’t crazy about each other.”

Until he sat next to her on the flight to Sacramento.

“The first thing I noticed about her were her eyes,” he said.

"As we sat next to a drunk guy all the way to Sacramento, Patty and I talked. It was comfortable."

At the conference, Ray listened to Patty speak, and he promptly updated his opinion of her. Patty’s “rebelliousness” and “confidence” captured his attention.

That night, the conference had a dance. Ray remembers that Patty wore “that coffee-brown short dress.” That dress left a stain on his mind like a grande-sized cup spilled on a white shirt. They danced, and discovered that they both love cumbia music, and La Sonora Santanera especially.

“After dancing for hours, we kissed,” Ray said. “And that was it.

“I realized two years into our relationship that I could trust Patty with my dreams, and she had faith in my ambition. She made me a better man.”

"Till infinity"

Ray proposed on his birthday. Upon deciding that her boyfriend was serious, Patty agreed to marry him.

Two children have followed. Adrian is in middle school, playing video games and taking vocal lessons.

“I never get tired of listening to my little boy sing,” Ray said.

Angela is a third-grader, and taking on the traits of her mother. “She has a strong sense of justice on the playground,” Ray tells me…and a strong rhythm on the dance floor. Angela is learning the flamenco, and carries herself like Patty: “Confidence and poise.”

“I could watch her dance forever,” Ray tells me.

Someday, of course, Ray and Patty’s little girl is going to dance her way into some guy’s heart, and someone else’s little girl is going to transform their video-gaming young man into a better man. Those outcomes are many years away, though, but Ray said he is confident today in how his family's future will unfold, because of the girl who loved him empty-handed.

“She would be someone who could help me dream,” he said. “She was the one.”

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At peace amongst the noise: Mike and Corey

In the cacophony of empty chatter, the voices of Mike and Corey stood out to each other. Whether amongst the blaring music at a mutual friend's house party or the buzzing background noise of Wrigley Field, this pair found that they would just rather listen to each other.

"We both liked having someone to talk with," Mike told me.

I met Mike and Corey and their two children, Dylan and Kennedy, for a holiday-greeting-card portrait session in the Cook County Forest Preserves. Kennedy plays soccer at her school, but Dylan is a left-handed pitcher at his. The boy has become a follower of the White Sox, which has become a source of consternation in the otherwise Cubs-aligned home. I interviewed them back before the World Series began; Mike is a native of Youngstown, Ohio, but he told me prior to Game 1 that he would cheer for the North Side over the Cleveland Indians.

"I live in the shadow of Wrigley Field," he told me. "I grew up a Tribe fan, but I live here now."

As a single young man, Mike landed on the North Side when he moved to Chicago; he made friends, and started attending parties at their houses on the weekends. Through a confluence of connections, he kept hearing one particular voice at some of those gatherings — and the voice was connected to a particularly lovely face. Corey's.

Corey looked at Mike's face, and immediately saw...some guy's face.

"He was nice," she said of that ker-plunk first impression.

But Corey was raised in a family of Cubs disciples, and Mike had bought into a season-ticket package with some friends. Upon learning this, hanging out with him became a larger priority.

"I wanted your season tickets," she confessed to him during our interview.

Even during the ugly, 100-loss seasons that preceded the 2016 world championship, Wrigley Field is usually a crowded and buzzing place on game days. Mike and Corey tuned it all out, though. Once they got together, even the crack of a bat got relegated into the background.

Mike and Corey have followed each others' voices for a long time now.

"That ended up being a lot of what we do, is just share a story," Mike told me.

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Hancock High School's graduation: "We go for everything"

National Honor Society members Selena Antunez (speaking) and Valerie Diaz deliver the Reflection speech

I've photographed plenty of high school graduations before, but they've all be out in the suburbs. Watching a group of genuine city-of-Chicago kids take the rite of passage into adulthood was something different — and worth seeing.

A father greets his daughter as Hancock's Class of 2016 walks into the theater

"Many of us here come from households who don't have as many opportunities as other people might have," National Honor Society member Valerie Diaz told her classmates. "Some of us are undocumented, while others are fighting money problems. Yet many of us will be the first to graduate from high school in our families.

"Many of our parents told us 'Ponte las pilas,' which literally means put the batteries in,'" she continued. "After everything that has happened, we are all in the same room because of what we have accomplished these past four years."

The Merle Reskin Theatre

Maximiliano Gomez and Jessica Herrera: the closing speech

Valerie Diaz (speaking) and Selena Antunez

"We just proved ourselves today by walking down this stage, so it’s time we go for everything they said we couldn’t have" said Jessica Hererra. "Now it’s time to take action. We are the voice of our people and of future generations, so it’s up to us to see what we do."

Juan Melendez

Michael Zapata

"We don't know we have unconditional love until we need it," Selena Antunez said in the Reflection speech.

"I learned that everything we do doesn't only affect us but the people around us, too. We have all learned to appreciate the people who care for us a little more, now that we are all grown up."

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The groom would like to share a few words

"I love our story," the bride told me. But it was the groom who told most of it.

The tradition of Donaldson's family. I'd never seen a dollar dance like this.

Donaldson had more to say about Scarlett than any groom I've ever spoken with. He started with the moment when he knew he was in love: At a mutual friend's wedding reception, when Scarlett brought him a glass of water.

"There was this sweet voice behind me, she said 'Oh, I thought you might be thirsty,'" Donaldson recalled. "Then I heard the bell going off, ding ding ding, this is your wife. It was all over a glass of water."

Well, there was a bit more to it than that. A lot of it happened while they were Skyping and baking.

Donaldson and Scarlett met through mutual friends Vinesh and Simi, and the couples shared a mutual headache: The ladies lived in Chicago, the gentlemen in London. For New Year's Eve 2012-13, Vinesh flew to Chicago to celebrate with his then-girlfriend, and Donaldson came along because...he's young, single, handsome, why not?

Donaldson spotted Scarlett, and was smitten right away — but she was seeing someone at the time. Donaldson the gentleman eased back...but Scarlett remained on his mind, across the pond.

Easter 2013, an engaged Simi flew to London to see her betrothed, and told Donaldson that she wanted to show him some photos of a nice young lady back in Chicago. Uh...Donaldson wasn't all that interested in checking out some girl in the colonies...until Simi forced one photo upon him.

It was Scarlett, who was free again. And Donaldson was still that smitten.

He gained sole possession of the key to Scarlett's heart: cyber-baking.

Through Skype, the two started cooking things at the same time, from their two apartments' kitchens. To accommodate the time difference, Donaldson would get up at 6 a.m. on Saturday mornings, while Scarlett stayed up past midnight on Friday nights. The groom quickly came to enjoy the early alarm setting.

"I was like 'Oh my gosh, this is so cool.'"

They e-mailed each other ingredients lists in advance. Donaldson once forgot the butter for a cake they were making. His did not come out well.

When Vinesh married Simi, Donaldson came back to Chicago, and made a point of spending time with Scarlett during the reception. This is where the glass of water and the dinging bells happened.

I got almost all of these details from Donaldson — the most conversational groom I've worked with so far. He proposed in October 2014, and Scarlett had this to say about that night: Once he started to kneel, he did not need to speak another word.

"As soon as he went down on one knee, I said 'Yes.'"

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Tipped in their favor: Andy, Lety and all that followed

Being an attorney, Andy is constantly trying to tip an otherwise balanced scale in favor of his clients. When he talks about how he fell in love with his now-wife, Lety, he makes a motion that comes naturally to him: hands out, palms up, one moving up while the other dips. He recalls the moment when his nascent attraction to Lety was on a scale like that:

"Was I going to call her? Was I not going to...?"

Finally, he made up his mind: he wasn't. Andy lost track of Lety's number, and didn't call.

I had a good time with Andy, Lety and the kids at the Chicago Botanic Garden

But the scale tipped back.

Andy first met Lety in 1998 through a function of the church they both attended, and liked what he saw. But a lawyer's training directs him to study each move before making it, and Andy put the idea of a romantic pursuit of Lety on the scale.

"He took my number, but he never called me back," Lety said.

Andy, Jr.

But sharing a social circle gave Andy another chance: he spotted Lety again at another social function months later.

He spoke candidly to me about his second impression. If you ever meet Lety, you'll understand this quickly: she is a woman of amazing grace.

"She wasn't dressed up as nicely, but the conversation was a little more substantive," Andy told me.

Diana

Andy asked Lety for her number again. Gracefully, she handed it over again.

This time, Andy called. Many more substantive conversations followed.

"We had similar goals, similar aspirations," he told me. "I could tell her anything and everything."

On March 11, 2000, Andy knelt down and asked Lety to dress up for him again. Lety accepted. Their lives merged, and Diana and Andy, Jr. followed.

The scale is tipped heavily these days, but Andy said he feels balanced now.

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Phil and Amy: "I believed what she was singing"

The irony in Phil’s telling of the story of how he met Amy, fell in love with her and married her is that while he loads most of it with rich details, he cannot remember the most crucial point.

“I blacked out during the proposal,” he told me during our pre-wedding interview.

He then turned to his bride for help remembering.

“What did I do?”

The story of how these two came together begins decades before either of them were born, in a jewelry store in Indiana; it includes hospital rooms, blues nightclubs and Ball State University. It does not include any NFL playoff games, and we’ll get to the reason why in a few paragraphs. But it also include’s Amy’s cat, Saffron, and Amy’s reminder to Phil that she was feeding Saffron is what brought the crucial detail of his proposal back to his mind.

“As soon as you said ‘cat food,’ it all came back to me,” he said, his face lighting up again.

The backstory of Phil and Amy begins in rural Indiana, probably in the early 1940s. No one knows who made the ring that Phil slid onto his bride’s finger, but its style is indicative of World War II work: white gold, with diamonds in a design halfway between an oval and a marquee. Phil’s step-grandfather, Merle Russell, was a jeweler, but the ring Amy wore does not bear much resemblance to any of his other pieces; he likely acquired it somehow, and may have lost track of it…

….And that might be how it ended up in a black bag, tucked into the back of one of his safes. Merle died in 1981, and when his descendants cleaned out his store, the mysterious ring surfaced.

“My mom pulled it out, she loved it, so that was my mom’s ring,” Phil told me.

The story pauses for two decades. In October 2000, Amy had been in publishing for years, and now worked for a music-production company called Chick Singer Night; she was a chick singer herself, an alto who loved to sing blues, and her first gig at a Chick Singer Night event was coming up. Phil was a professional drummer, inspired by Coliauta, Gadd and Williams; he often played with a house band, and he loved the blues. For her first concert, Amy would be singing in front of a house band.

Hours before showtime, Amy rehearsed with the group. During the down time that divides rehearsal from performance, Amy sat at the bar, and the drummer pulled up next to her.

“We were talking, and we discovered that we both went to Ball State,” she recalled.

The two conversed, and time passed, and their talk had to conclude when showtime arrived.

“Internally, I have such stage fright,” Amy told me.

“I never really noticed it,” the man who played drums for her that night told me.

“I don’t remember my performance,” Amy said.

“I remember her performance vividly,” and Phil pulled it back to the present, in sharp detail,15 years after it happened. “I’m not going to sugar-coat it: I thought she was a decent singer,” he said. “But I believed what she was singing.”

But the time was not right — the two parted ways, and nearly 10 years went by. Amy and her friend Becca founded the Singer Spotlight series in January 2001, and celebrated its ninth anniversary in January 2010; Phil came to that show to watch some of his friends, who were in the house band. Greg, the bassist, had become a friend of both Phil and Amy.

“Greg told me we’d be great together,” Phil recalled. “I himmed and hawed around about it for a while. Finally, I Facebooked her, and asked if if she’d like to go out with me.

“She told me she’d take a raincheck on it.”

Amy took Phil’s request for a date, and her postponement, to her business partner. Her business partner disapproved of this move.

“Becca just reamed me out,” Amy said. “She was like ‘You are dumb, this is a great guy!’

“So I wrote him back, and said ‘How about that raincheck?’”

Their first date was on a Saturday; they planned to tour the modern art wing of the Art Institute of Chicago. Phil had a problem: his favorite NFL team, the Indianapolis Colts, was in the playoffs, and had a do-or-die game during that time.

So they had an “unofficial,” as Amy put it, preview date the night before: Becca’s birthday party at Fitzgerald’s. They stayed until 3 a.m. The next day, they met at the Art Institute.

“That date ended up being eight or nine hours,” Amy told me. “After that date, we called each other almost every day.”

Phil skipped the game. The Colts won. His team was on their way to Super Bowl XLIV.

But he was on his way to securing his own grand prize.

“She laughs at my dumb jokes,” Phil told me. “Which aren’t dumb, but, after you hear them for the ninth time, maybe they are. I feel loved and cared for in a new and refreshing way.”

“I think, intellectually, we’re on the same plane,” Amy explained. “I never get tired of talking about things with him.”

Amy and her mother, Kathy

But there was more going on in Amy’s personal life than a blossoming romance. Her mother, Kathy, was suffering from stage-four breast cancer, which had metastasized to her bones. Doctors told Amy that she would lose her mother soon.

She did not. Kathy celebrated her 81st birthday in September, then watched her daughter marry Phil in October.

“She’s a woman of amazing strength and determination,” Amy told me. But at the time, Amy was frightened, and spending as much time as she could with her mother, in the hospital.

Phil had been trying to sneak questions about Amy’s ring size into conversations around that time. At home one evening, when he knew that she would be rushing between work and the hospital, he wanted to get her complete attention for a moment.

He had Merle’s ring with him. His mom had taken it off of her own finger, resized it and given it to him, so he could propose with it.

Kathy shows a guest Amy's baby photos

Amidst sorting things out and getting ready to visit Kathy, Amy stopped for a second to feed her cat. She turned around — and Phil was holding an open box. The ring his mother wore was inside.

“He was like ‘So, do you want to get married?’” Amy recalled.

“She was ‘gobsmacked,’ I call it,” Phil told me.

“And I was like ‘Yeah,’” Amy said. “After he proposed, I calmed down a little bit.”

In trying to tell his side of all this to me, Phil got stuck at trying to describe the proposal. What jogged his memory: Amy mentioned the kidney disease Saffron was struggling with, and how she was feeding him Royal Canine cat food. Once she mentioned that, Phil’s “blackout” moment filled with light.

On their wedding day, Merle’s ring filled the Frederick Graue House with light.

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