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The Winning Ways of a Thirty-year Loser
Gerald Holland
November 23, 1964
When Art Rooney founded pro football's Pittsburgh Steelers a black notebook served as his office, a handshake closed his deals and he dreamed of championships. Since then he has become a millionaire, made a million friends, built a million-dollar racing interest and has given up trying to run things from a black book. But he and Pittsburgh are still looking for that title
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November 23, 1964

The Winning Ways Of A Thirty-year Loser

When Art Rooney founded pro football's Pittsburgh Steelers a black notebook served as his office, a handshake closed his deals and he dreamed of championships. Since then he has become a millionaire, made a million friends, built a million-dollar racing interest and has given up trying to run things from a black book. But he and Pittsburgh are still looking for that title

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Rooney's induction into the professional football Hall of Fame in Canton, Ohio in September brought out another rash of complimentary notices, including mention of his celebrated betting coup in 1937 when he was reported to have won a quarter of a million dollars at New York's old Empire City track and at Saratoga. ( Rooney professes not to know exactly how much he won but admits that it was "quite a lot.") Mention of Rooney's big score quite naturally led newspapermen into recalling that he sent a large share of his winnings to a Pittsburgh orphanage, another bundle to his brother, then a missionary in China, and scattered smaller gifts to down-and-outers who came running to congratulate him.

There is only one act of charity that Rooney willingly recounts. "I was at the races at Narragansett one day and happened to have a winner. I was coming away from the cashier's window when I noticed a little old lady dressed all in black. She was standing against a wall, crying bitter tears. I walked over and said, 'Ma'am, are you ill? Can I do anything for you?' She turned to me, the tears streaming. 'No, sir,' she said, 'Nobody can help me now. I've lost my rent money and the medicine money for my little grandson who's lying there in our furnished room getting weaker by the minute with the whooping cough. I came out to the track, praying that I would have a winner to buy medicine for the little tyke. But my horse lost by a lip, and now I don't know what to do. But it's all right, sir. Don't you mind. You're a fine gentleman and you just go ahead and enjoy your winnings with a champagne and lobster dinner somewheres. I'll get by somehow.' Well, I reached into my pocket and pulled out a $100 bill. 'Take this, my dear lady,' I said. "Pay your rent and get the medicine for the little boy. Say a prayer, and I'm sure something good will turn up for you.' Well, on the way to my hotel. I was riding with a well-known tout and I told him the story. I thought he would laugh himself sick. "You've been taken by Winnie the Weeper,' he said. 'That old doll has been hanging around the $50 cashier's window and working that act with strangers for years.' "

Rooney shook his head. "I still think The Weeper deserved the money. She gave a great performance."

With Art Rooney playing himself down and public speakers and sports-writers playing him up, it is difficult to get a dispassionate opinion about him.

Of course, if Rooney were ever to agree to the proposition that he run for mayor (an idea that occurs to his admirers from time to time), some political opponents might come forward with insinuations and innuendos calculated to tarnish his public image. It might be recalled that he was the right-hand man of State Senator James J. Coyne, the Republican boss of the 1920s and 1930s, a time when bootlegging, bookmaking and other diversions are said to have flourished on Pittsburgh's North Side. It might be mentioned that Rooney did nothing that could be construed as an unwillingness to aid and abet Senator Coyne in his efforts to run Pittsburgh for the greater good of the Republican Party. No doubt a political foe would deplore Rooney's associations with bookmakers and piously wonder aloud about that great betting coup of 1937.

But it wouldn't work. For one thing, Rooney's association with Senator Coyne, the onetime political boss, has been turned to his advantage. Former Governor David Lawrence, now a special assistant to President Johnson at the White House, says: "Art is a true-blue kind of guy who will be with you when you lose. His deep loyalty to Senator Coyne as a leader on the North Side made a lasting impression on me. When Coyne was on the way out, and the rats were skipping ship to join the Democrats who were on the way in, Rooney stuck with Coyne to the bitter end. That's the quality I admire most in a man." As for Rooney's adventures as a horseplayer, there is no record of a man losing large numbers of admirers by beating the races.

Of course, Rooney has no intention of running for mayor or anything else. In view of his dislike for making formal speeches, he probably would not make much of a campaigner. His talent is in personal contact with people; like many another old-line politician, Rooney has a way of convincing a man that running into him has made his day. "I want you to know," he may say (perhaps to a person of some importance or to an usher at the racetrack), "that I always enjoy your company. Just talking to you gives me a lift. Everybody who knows you speaks well of you."

In Pittsburgh only a few old pals have ever talked about Rooney with anything less than reverence. One of these was the late Owney McManus, a veteran of decades of Pittsburgh political wars.

" Rooney! Rooney is a scoundrel," Owney McManus liked to say as a preamble. Then you could all but see him step up on a large soapbox—large because he was a short man, a handicap in the days when a precinct politician wasn't much better than the distance his voice would carry—and you could brace yourself for an address.

"Oh, that Rooney!" Owney McManus would say. "The things we have been through. Now Art, he was Republican boss of the 22nd Ward and I was head man for the Democrats in the Second. But that didn't affect our friendship. We used to make the round of saloons together, the sawdust-on-the-floor joints, mind—we never went to cabarets. Now, it was my ambition in those days to get a saloon of my own. I thought if I could have my own place I could have my own way and be looked up to, don't you know? Well, I finally realized my ambition. I got a place near City Hall, and it was a grand success. It became the official hangout for newspapermen, politicians, judges, prizefighters, football players, bookies—all first class. I was in my glory. I was there early and late. Naturally, I had to drink with the boys and, as the day wore on, the effects began to show, I suppose. I've always been a great talker, but I never thought I was getting out of hand until my customers took it into their heads to throw me out one night. 'On what grounds?' I demanded to know. 'I own this place. On what grounds is the proprietor thrown out of his saloon?' They'd make some claim that I was guilty of monopolizing conversations. Pretty soon I was being thrown out of my own saloon every night. And did Art Rooney come to my assistance? He did not. 'Art,' I'd plead with him as they hustled me to the door, 'Art, stop them! Let reason prevail here, Art! Remember what we've been through together!'

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