Boxer Tom O’Shea, a father figure to Chicago high school students he coached, dead at 81

Tom O’Shea taught his students to love Hemingway and Gwendolyn Brooks and also how to deliver a good left hook.

As a young man, he fought in the same tournaments as Muhammad Ali. He went on to be a high school English teacher and boxing coach who sent the students he called his “Matadors” on to the Olympics, Hollywood and productive lives.

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He was one of Chicago’s “Fighting O’Shea Brothers.” Back when the city’s Golden Gloves boxing finals were one of the nation’s hottest tickets, the four Irish immigrant siblings were some of its most popular pugilists. This was an era long before people had hundreds of TV channels, streaming and video games.

All four O’Sheas — Brian, Michael, Rory and Tom — fought in national Golden Gloves competitions in the early 1960s. Brian, Rory and Tom won at the national level — Tom in 1961, according to the book “Chicago Amateur Boxing.”

They fought at some of the same amateur tournaments as the young Muhammad Ali, then known as Cassius Clay.

“Muhammad Ali was in the family house and visited my Irish nana,” said Laurie O’Shea, Tom’s daughter.

“He came over to the house and had tea,” said another daughter, Colette O’Shea.

Their mom never wanted her boys to fight each other. So the O’Shea brothers used to work out which of them would gain or lose a few pounds so they could compete in different weight classes.

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Thomas, who fought 378 amateur bouts without a loss, became a Chicago teacher and a boxing coach to thousands of kids who called their mentor simply “O’Shea.”

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He sent three boxers to the 1996 Olympics: Anthony Stewart and Darnell Wilson, all as alternates, and Nate Jones, who dedicated himself to boxing after serving time for armed robbery. Jones won a bronze medal in Atlanta and now trains fighters in Las Vegas, where he works with boxer Floyd Mayweather.

“He made me feel great,” Jones said. “He made me feel like I was important in life.”

Actor Joseph Sikora, who starred as Tommy Egan on the Starz TV series “Power,” calls Mr. O’Shea “my hero.”

Joseph Sikora / Instagram

“O’Shea often referred to boxing as a metaphor for life,” said Sikora, a former Norwood Park resident. “There is nowhere to hide in the ring. Being an actor and a writer is an unbelievably brutal business to try to go into. I didn’t have any connections when I started, but I applied those same rules that Coach O’Shea taught me: Listen to people who you trust, work hard, and just fight like hell.”

Mr. O’Shea’s family had been considering holding a memorial service for him in August, when he would have turned 82. But it’s been hard to think about. They remain stunned over his death in April from the coronavirus.

“We’re still in shock,” Laurie O’Shea said. “In December, he’s in his winter coat walking in Winnemac Park. Four months later, he’s not on the planet anymore.’

After tearing a groin muscle in a fall, Mr. O’Shea, who had Lewy body dementia, entered a North Side rehabilitation facility. But when his daughters learned another patient there had tested positive for COVID-19, “We pulled him out immediately,” she said.

They moved Mr. O’Shea back to his Lincoln Square home, but he, too, developed the coronavirus and died April 16.

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For comfort, his family set up a shrine to him on their dining room table. It includes books by some of his favorite authors, family photos and memorabilia about the sweet science. It makes them feel as if he’s joining them for dinner.

Young Tom was 13 when the O’Sheas immigrated from Dublin to Chicago in the mid-1950s. His father William, a plasterer, arrived first, then sent for his wife Josephine and their six children.

“My grandma came over on the boat with the six kids,” Laurie O’Shea said.

In Ireland, the O’Sheas had been taught by the Christian Brothers. Their disciplinary methods sometimes included an invitation to put on boxing gloves and face off against the brothers.

“Everybody fights in Ireland, whether you like it or not,” Mr. O’Shea once told the Sun-Times. “I was coached by priests and Christian Brothers. It’s almost like a religion there.”

In Chicago, he was coached by Tony Zale, the former world middleweight champion known as Gary’s “Man of Steel.”

Over the years, he had some ribs broken and cracked his front teeth, according to Laurie O’Shea. Still, he could dance around the ring.

“I was a different kind of fighter than my brothers,” Mr. O’Shea once told the Chicago Reader. “They were tough guys who could knock you out with a punch. My claim to fame was I never got knocked down in 378 amateur fights. I was fast, I moved around. Sometimes, it’s more important to avoid getting hit than it is to hit. It’s as true in life as it is in boxing.”

The O’Sheas grew up in the 2500 block of North Halsted Street and belonged to St. Clement’s parish. Tom, the oldest, and his brother Brian, the second oldest, dropped out of school to get jobs and help pay the mortgage, according to Laurie O’Shea.

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At a social at St. Lucy’s parish on the West Side, he met Sally Stapleton. They got married, and she worked at a bank to put him through school. He graduated from Austin High School and earned a bachelor’s degree at what’s now the University of Illinois at Chicago and a master’s degree in English from Northeastern Illinois University.

In the 1970s, he started teaching at Sullivan High School. After moving to King High School, he started a boxing club he called the Matadors.

“He brought in Joe Frazier, Julio Cesar Chavez and Roy Jones Jr.” to talk with the kids, said Colette O’Shea.

His ring philosophy was: “Be the Matador instead of the bull.”

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“Many students don’t accept what I can give them in the classroom,” Mr. O’Shea told the Sun-Times in 1988. “There is so much youthful energy out there and so many negative channels. This is one of the positive ways of using it.”

When his athletes triumphed, “He would call up the school and have their names announced that they won certain tournaments and have them announced in the [Chicago] Defender,” Colette O’Shea said.

He continued coaching the Matadors after a transfer to Wells High School.

Mr. O’Shea also coached at Seward Park near Cabrini Green.

“My dad would give up his pay at the park and say, ‘Give it to the kids, give them summer jobs,’ ” Colette O’Shea said.

Often, he’d buy dinners for the kids, who were starving after their workouts, his family said.

“America fed him,” Laurie O’Shea said. “He paid that back by trying to create a better life for kids.”

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He also coached at Eckard Park and the Northwestern Settlement House at 1400 W. Augusta Blvd., where Sikora started taking boxing lessons as a teenager in 1993.

In a posting on Instagram, Sikora wrote that Mr. O’Shea “loved poetry and Shakespeare. He was an English teacher and would help me with homework after boxing and came to see me along with his daughters, Laurie and Colette, in every play I did in Chicago and unlike almost everyone else, encouraged me to pursue a life in the arts.”

“I’m a Matador for life,” Sikora told the Sun-Times. “It means that you put on the gloves, got in the ring and fought as a Matador. Unlike a lot of coaches around the city, ‘being tough’ wasn’t on O’Shea’s agenda. It was about learning the chess match that boxing can be.”

“Boxing also gave me the coordination that I have used time and again on film sets in fight sequences,” Sikora said.

A former King student credits Mr. O’Shea for his career.

“If it wasn’t for him, I wouldn’t be in the position I’m doing now,” said Rodney Wilson, 52, a boxing coach for the Chicago Park District who’s Darnell Wilson’s brother. “I’ve got kids coming to me like I did with O’Shea. I honor that.”

Mr. O’Shea didn’t hang onto possessions, according to Laurie O’Shea, but she said, “He saved three T-shirts, and they all had Muhammad Ali’s name on them.”

In addition to his daughters and former wife Sally, who took care of him when he was ill, he is survived by his brother Brian, sister Teresa and grandson Liam.

One of his proudest days “was the day they named Norah O’Donnell anchor” of the CBS Evening News, Laurie O’Shea said. “For him to see a gorgeous woman with an Irish name do the evening news was the punctuation to his life. It was a big moment for him.

“He wasn’t ready to go, that’s for sure,” she said. “He just wanted another great day. Another great evening watching Norah O’Donnell. Another great meal.”