Chatham’s TailoRite Has Made White Sox Jerseys Perfect For Game Day For 29 Years — And It’s Stayed True To Its South Side Roots

CHATHAM — It was opening day 1992 for the White Sox, and Joseph Caldwell Sr. had a prime spot: right behind home plate.

The Sox had inked Caldwell’s company, TailoRite Complete Clothing Care, to a contract that offseason, making it the first Black-owned company to clean professional baseball jerseys. The Sox fan was up all night cleaning, repairing and pressing uniforms.

The team gave Caldwell his pick of seats at Sox Park — but he dozed off by the second inning.

“I needed to do a perfect job,” Caldwell said. “There was a lot of pressure, being the first Black American to do it: ‘If I mess this up, Major League Baseball is going to know about it.’ I had to make a good impression.”

Caldwell and his company have cleaned the White Sox jerseys for 29 years and counting. The contract has opened doors for TailoRite to expand and paved the way for more Black-owned vendors to work inside Sox Park, Caldwell said. 

Baseball is back on after a lockout canceled the start of the season, and Caldwell can’t wait for Sox jerseys to come back to Chatham. 

“I’ll be ready. We know how to do the job,” Caldwell said. “You got to make sure the letters are straight, the spots are out, all the sand from sliding gone, the tears repaired, zippers working; whatever makes the uniform ready to wear.

“It’s an art form, and we’ll be ready.” 

‘We’re Gonna Fix It Up Right’

TailoRite has been in business on the South Side since 1956. It has locations at 8459 S. Cottage Grove Ave. and 6507 S. King Drive.

Caldwell, now 89 years old, said he’s “semi-retired” but still comes to work every day. He inspects every Sox jersey before they leave his shop. 

“Baseball players are kind of superstitious. They like to play in the things they win in. If the Sox are winning, he wants that uniform,” Caldwell said. “And if they send it to us, we’re gonna fix it up right.”

At the 6,000-foot TailoRite shop on Cottage Grove, mentions of the Sox are kept to just a few framed photos above the front counter. In the back, sewing machine No. 3 is reserved for the team, ready with black thread for the team’s jerseys. When a player gets traded or signed, Caldwell sits here, sewing the name and number onto the jersey.

The 2005 World Series was “a real hustle,” Caldwell said, as his team had to sew hundreds of patches onto Sox jerseys. Former Sox manager Ozzie Guillén, impressed by Caldwell’s work, still sends his suits to TailoRite. Opposing teams often trust TailoRite to wash their uniforms when they play the Sox. 

Caldwell has never lost a jersey. 

“It’s just a prideful thing. You see that uniform on the field, and they look good,” Caldwell said, smiling. “That’s important to us.”

The business’ partnership with the White Sox came through its South Side connections: The architect of Caldwell’s building knew a pastor who knew White Sox owner Jerry Reinsdorf, who was looking to support minority-owned vendors as part of baseball’s Equal Opportunity Committee. Baseball has long struggled with diversity in hiring — from the front office to the less visible positions — and Reinsdorf had spoken about that issue.

Michael Spidale, director of purchasing for the Sox, said greater consideration for Black vendors made business sense, as it increased the number of bids on contracts. At the time, the Sox were sending their jerseys to suburban Schaumburg.

In 1991, Spidale met Caldwell, handed him a Sox jersey and asked, “Can you clean this?”

“We just got right down to business,” Spidale said. “Right away, I could tell Joe ate, drank and slept tailoring and clothing. He’d been in the business for years. He was very professional. And I got the immediate feeling he was a man of his word. That he was able to do it, and he’ll get it done.”

Caldwell, a White Sox fan, was shaking.

“I had not talked to a major corporation like that before,” Caldwell said. “But I looked at the care label and realized right away we can do this. [We’d] been cleaning for 35 years; if anyone can clean them, we know how to clean them.” 

Caldwell took the jersey back to Chatham and “tooled up” for the big leagues, buying speciality machines despite being uncertain how long the partnership would last. At first, the job would “scare the blues out of you,” Caldwell said. His shop had only done retail before, fixing up suits and dresses for weddings, parties, proms and funerals. 

Caldwell remembers the first time he pulled up to Comiskey Park in his TailoRite truck, passing jerseys to the clubhouse manager, who was also Black. 

“He said, ‘I’ve been waiting 22 years for you,’” Caldwell said. 

‘This Was My Dream’

Caldwell has stood out among entrepreneurs because he scaled up his business without leaving his home, the South Side, said historian Shermann “Dilla” Thomas. Thomas learned about Caldwell while researching notable people from Chatham. 

“Staying in Chatham is a visionary decision. A lot of times, successful Black businesses chase the high-end customers, jump to the North Side and then find themselves priced out,” Thomas said. “But a place like Caldwell, they’re invested in their service. They have a sense of community obligation. And that’s what’s made them successful.” 

Caldwell said he’s helping support neighbors — and it’s important the White Sox keep their uniforms on the South Side.

“That’s putting money back into the community,” Caldwell said. “I got Black employees, people paying college tuition, buying homes, cars, living the American dream; that’s what builds a community. And we need that. Every community needs that.”

Caldwell was born in Arkansas, served in the Korean War and came to Chicago looking for opportunities during Chicago’s second Great Migration. He got his first job driving the No. 152 Addison Bus past Wrigley Field. 

Caldwell pursued trade school and went into business with his teacher in 1956, opening the first TailoRite shop at 16 E. Garfield Blvd. They replaced zippers and buttons.

The success of the shop had Caldwell hoping to open a full-service cleaning location, but he couldn’t get a loan from white-owned banks Downtown. An investment from Seaway, a Black bank around the corner where members of the board were Caldwell’s clients, gave him the $3,500 he needed. 

Caldwell opened his flagship Cottage Grove location in 1987.

“This was my dream,” said Caldwell — suit and tie freshly pressed — as he gave a tour of the shop last week.

Caldwell’s brother, Charles Robinson, works the washers and spots the stains in the backroom. He’s “the man in the back who backs me up,” Caldwell said. Caldwell’s daughter, Veta Caldwell-Charles, answers the phones upstairs. 

The White Sox job has helped the family create generational wealth, Caldwell said. Caldwell-Charles, at her desk across from her father’s, drummed off the list of large corporate accounts TailoRite manages: McCormick Place, United Airlines, GardaWorld Security, the Judge Mathis show and Operation PUSH, among others. 

“From that seed when someone knows you know how to do something, the White Sox are trusting you — you’re able to fulfill that promise to other people,” Caldwell-Charles said. 

Caldwell smiled at his daughter. 

“The thought was if we can do the White Sox, we can probably do anything,” Caldwell said.

There are still concerns. Caldwell said there hasn’t been improvement in diverse hiring in baseball operations. And middle-class Black Businesses “have declined” during the pandemic, he said, though he feels fortunate TailoRite has rebounded.

But Caldwell’s looking forward to the season.

The White Sox “look good on paper,” Caldwell said. His shop put up a White Sox “World Series Champions” banner outside in 2005 — and he thinks they’ll have to get another.

“This will be the year, though,” Caldwell said. “We’ll have to put another one here in Chatham.” 

---

Listen to the Block Club Chicago podcast: