‘First Lady’ of Pirates: Sheffield’s O’Leary meant a lot to team, baseball

Sally O’Leary learned to type at Sheffield High School.

That typing skill helped her land a job with the Pittsburgh Pirates in May of 1964, and she’s been with the team ever since.

“I’ve had a great career,” said O’Leary. “I’ve seen so much.”

After a career that will hit 50 years in May, O’Leary never expected to be the first recipient of the Distinguished Women in Baseball Award at the Rotary Club of Pittsburgh’s seventh annual Chuck Tanner Awards Banquet on Nov. 16.

More than that, O’Leary certainly never expected the award would now be named after her – the Sally O’Leary Distinguished Women in Baseball Award.

“That blew my mind,” she said. “I’m not sure when that sunk in. They asked me to work with them to pick next year’s winner.”

But before O’Leary, now in her late 70s, was the “First Lady” of the Pirates, she was a student at Sheffield High School.

“I’m so proud I grew up there,” O’Leary said. “I still have friends I grew up with in Roystone.”

Her father, brothers and one of her sisters worked for Pennsylvania Gas their entire lives. Growing up, O’Leary’s father was the superintendent there. “I was very fortunate growing up there.”

O’Leary moved to Sheffield in 1948 after her father’s retirement, and graduated from Sheffield High School in 1952. From Sheffield, O’Leary moved to Buffalo, N.Y., to attend Bryant and Stratton Business College. She interviewed with insurance companies, but advertising was “the best break” she ever had.

In 1957, O’Leary made the move to Pittsburgh to live with her sister and was finally able to go to Major League Baseball games after going to minor league games in Buffalo.

“My sister and I went to games quite often,” O’Leary said.

O’Leary met MLB all-star Frank Gustine at his Pittsburgh restaurant, Gustine’s, in the late ’50s. When a group formed the Gus Fan Club, O’Leary went to the luncheons with the club at the Roosevelt Hotel during baseball season. It was there that she met local media, baseball players and then-Pirates announcer Bob Prince.

At the time, Mellon Bank was a sponsor for the Pirates and O’Leary was working in traffic control for those commercials. Her name appeared on the commercials as a contact and “Bob would call about commercials,” O’Leary said.

Prince and O’Leary became friends. Knowing that O’Leary had applied for jobs with the Pirates and received form letters back, Prince stepped in.

“He said, ‘Someday there will be an opening and I’ll see that you get the job,'” said O’Leary.

That day came as O’Leary was reading the morning paper in May of 1964.

“The paper said the girl in PR was leaving the Pirates after 11 years to move back to Philly,” said O’Leary. “The Pirates were on the road. Bob called me and said, ‘I’ve already set up the interview for next Saturday at Forbes Field.’

The next Saturday, O’Leary sat down with Jack Berger, the PR director for the Pirates, in the stands during a game.

“He called me Monday morning and said, ‘There was one thing I forgot to ask you: Can you type?'” said O’Leary. “I learned to type at Sheffield High School!

“I was so excited to get the job,” she said. “I hated math, I absolutely hated math. But there was statistics every day without a calculator. I had to use a guide book to get batting averages – I didn’t care. I had the job and I would do anything to keep it. I loved it.”

O’Leary was a PR assistant from the beginning at a time when there weren’t many women in key MLB positions. There were 25 people in the office at Forbes Field. When the team moved to Three Rivers Stadium, the office expanded.

“Everyone had a private office – we had a huge file room for all of the players’ files and photos and all modern equipment to work with,” said O’Leary.

With the expanded staff, O’Leary no longer needed to take statistics or be at every game.

That lasted all of one game.

“They needed help with the scoreboard and that opened up a whole new avenue,” said O’Leary. “I learned computers, I typed messages for groups and when players were close to records. You could cheer as much as you wanted because you were behind glass and no one could hear you, unlike the press box where you weren’t allowed to cheer.”

O’Leary was involved throughout the game. She provided information in the broadcast booth during the televised Game of the Week as the eye for the announcers, resulting in her working with people like Joe Garagiola, Tony Kubek, Bob Costas, Curt Gowdy and even Leo Durocher for a couple of games.

O’Leary has seen Pirates history first-hand. She was with the club for the 1971 and 1979 National League Championship Series and World Series and the All-Star Games in 1974 and 1994, and did all kinds of work behind the scenes for all of those.

With all the history O’Leary has seen, she’s been told on more than one occasion to write a book.

“I’ve started making notes,” she said.

Through the years, players and staff have come and gone, but O’Leary has kept tabs on them through her work with the Pirates Alumni Association which she helped organize, along with Nellie Briles, in 1987. Today, there is a mailing list of over 600 former players, managers and coaches. She retired in 1996, but she still works with the team Alumni Association from home.

“This has been one of the most rewarding things I’ve been involved in,” O’Leary said. “The former players are so pleased to know they haven’t been forgotten.”

And O’Leary hasn’t been forgotten by the current players or coaches, either.

O’Leary began a friendship with Pirates manager Clint Hurdle through email after it was announced in September of 2012 that Hurdle would definitely be back for the 2013 season. O’Leary sent Hurdle a congratulatory email and received a response almost immediately after, “to thank me for the confidence,” she said. “I didn’t expect an answer!”

After the Pirates defeated the Chicago Cubs in September to seal their ticket into the post-season for the first time since 1992, O’Leary’s excitement kept her from sleeping.

“I was here alone watching the game and I couldn’t go to bed. I couldn’t sleep,” said O’Leary. “A little before 2 a.m., I thought, ‘I should go to bed.’ At two o’clock the phone rang and Greg Brown, the announcer, said, ‘I knew you’d answer.’

“I talked to players, to clubhouse guys, and then finally, Clint,” said O’Leary.

“I was speechless. I didn’t sleep for hours,” she added. “They wanted me to be a part of their celebration, even though I was in Pittsburgh and they were in Chicago. Pittsburgh’s a special city and we’re so lucky to have the teams that we have.”

Seems the Pirates are lucky to have O’Leary.