Although most current reference works assign Oliver Hazard Perry Caylor the nickname of Ollie and omit Hazard as one of his middle names, Caylor made it known that his full name included Hazard and he loathed the nickname Ollie, preferring to sign his correspondence either Opie or O.P. Caylor, depending on his spirits at the moment. Cincinnati owner Justus Thorner once described Caylor as looking “like a rotten tomato on the end of a corn stalk.” In what few visual images that linger of Caylor he seems singularly unimposing, fragile and quite in keeping with catcher Dan Sullivan’s jibe that he was hardly more than “a pimple on the end of a stick” and Gus Schmelz’s snide depiction of him as “a mongrel skeleton” after Caylor was instrumental in Schmelz being fired as manager of the 1885 Cincinnati club.
Yet, with a pen in hand, Caylor was lethal, the most superlatively caustic baseball writer in an era when journalism was a full-contact sport. The baseball men that he crossed swords with—and there were few that he exempted—were generally capable of giving as good as they got but almost always came out on the short end in exchanges with him. On the other hand, when Caylor was in a good mood he could write with unusual charm. But even then his adversaries had to be wary, because he was a master at stabbing people in the back while seeming to pat them on the shoulder.
Caylor was born in Dayton, Ohio, on December 14, 1849, to Henry and Mary Whittamore Caylor and was named after the famous United States Naval Commodore. After graduating first in his class at Dayton High School in 1870, he studied law in Dayton under Judge Gordon and was admitted to the Ohio bar in 1872 but chose instead to move to Cincinnati and cast his lot as a baseball newspaper columnist for the Cincinnati Enquirer and the Cincinnati Commercial.
By 1876, in addition to his journalistic duties, Caylor had joined the front office staff of the fledgling Cincinnati on National League entry and also served as the club’s official scorekeeper. In that capacity he was purportedly responsible on May 23, 1876, for costing Boston pitcher Joe Borden what many historians believe was the first National League no-hit game. According to some reports on the contest, in keeping with an unpopular rule in effect for that year only that awarded a base hit instead of a walk for every base on balls Caylor credited two Cincinnati batters, Charlie Gould and Charley Jones, with singles for what most other league scorekeepers chose to ignore as hits and count as walks.
In 1880 Caylor and Justus Thorner took over the ownership of the crumbling Cincinnati National League franchise. When it was expelled from the NL after that season, to return major league baseball to the Queen City in the winter of 1881-82 Caylor joined Horace Phillips, Al Pratt and Denny McKnight in the founding of the American Association as well as acting as the prime force in the formation of the current Cincinnati Reds franchise. After serving for three seasons as a club officer and general manager in charge of personnel decisions, he succeeded catcher Charlie Snyder as the field manager of the Reds in 1885 with mixed results. Caylor brought the club home 2nd in his initial season as a helmsman but lost control the following year when several key regulars had poor seasons and the club’s leading hitter, outfielder Fred Lewis, grew so corrosive while under the influence (an almost daily occurrence) that he had to be jettisoned. During most of the summer, the Enquirer referred to Caylor not by name but as "Miss Management” and dressed him in women’s garments whenever a cartoon of him appeared in its pages. Although he retaliated in kind, he resigned after the season, seemingly aware that his combative nature had put him irrevocably at odds with both his fellow members of the Cincinnati press and the Reds’ other owners.
Caylor then became one of Sporting Life’s feature writers until the spring of 1887 when he started a baseball paper of his own in New York with some financial backing from John Day and Erastus Wiman, the owners of the two New York major league clubs, but gave it up after only 10 days as The Sporting News chortled: “Caylor was never noted for his pluck but in this instance his courage seems to have oozed out at his finger ends before the real fight had commenced.” At loose ends, on June 13, 1887, having bought stock in the New York Mets from Wiman, he agreed to take over as manager of Wiman’s floundering 9-28 team and succeeded in lifting it from the cellar into 7th place in the American Association before it disbanded after the season.
Still seeking a proper haven for his mighty pen, Caylor moved to Carthage, Missouri, started another paper that failed and sold his interest to a man named McGillicuddy, who claimed to be a relative of Washington catcher Connie Mack (which was true and may have made Caylor the first baseball writer privy to Mack’s real name). Caylor returned to New York in 1889 as editor-in-chief of The Sporting Time. When that paper folded as well, he joined the New York Herald and remained a frequent contributor to The Sporting News and Sporting Life until his death. The Sporting News sounded an ominous note in its November 7, 1896, issue when it stated that he was gravely ill at his home in New York. Some nine months later, in its July 24, 1897, issue The Sporting News reported that “throat trouble prevents him from speaking above a whisper.”
Nevertheless, Caylor continued to write and plunge ahead with his life until September 1897 when he left his wife Luella (nee Pittenger of Henry County, Iowa, where the couple were married on September 13, 1876) and daughter Lenora (born in Cincinnati in 1883) behind at their home in New York while he went to Minnesota in a vain attempt to recover from consumption. On October 19, 1897, Caylor, who for years had signed his letters, “Yours as long as I last,” died among strangers in Winona, Minnesota. In addition to consumption, he had three small tumors in his trachea and apparently one of them burst and choked him. According to the October 23, 1897, issue of The Sporting News, his last act was to seize the hand of the nurse at his bedside and hold it.
At Caylor’s funeral in Dayton, where he was buried at Woodlawn Cemetery, Henry Chadwick delivered a lengthy eulogy, and Philadelphia Phillies owner John I. Rogers said in his turn at commemorating Caylor: “Those who first met him wondered at his frail and diminutive body which casketed the intellect of a giant.”
Caylor’s daughter Lenora maintained a close connection to the game after her father’s death. The May 1, 1909, Sporting Life noted that in her capacity as secretary to National League president Harry Pulliam on April 21, 1909, “Lenora V. Caylor” performed the unveiling of a memorial over Henry Chadwick's grave at Greenwood Cemetery in Brooklyn. Upon Pulliam’s death by his own hand Miss Caylor, who apparently never married, remained at her post under his successor, former National League umpire Tom Lynch, and later worked for NL presidents John Tener and John Heydler.
Left to future researchers are the puzzles of how Caylor, an Ohioan, met his wife, a native of Iowa, and why he chose Winona, Minnesota, as his final port of call.
This biography is an expanded version of one that appeared in David Nemec's Major League Baseball Profiles: 1871-1900 (Bison Books, 2011) vol. 2 and was written by Nemec with assistance from David Ball.
In assembling this biography I made extensive use of the Cincinnati Enquirer, the Cincinnati Commercial Gazette, the New York Times, Sporting Life, The Sporting News, the New York Clipper, the Cincinnati Historical Society and Find a Grave on the Internet.