After holding out over a temperance clause the Chicago Orphans added to his contract, Bill Phyle finally signed in late March of 1899. He reported to spring training in New Mexico anywhere from 10 to 30 pounds overweight (depending on the source) and struggled all season to regain the form he showed the previous season.
On April 17 he was beaten 8-0 by the Louisville Colonels in first start.
On April 25 he lost 3-2 to the St. Louis Perfectos. The Chicago Tribune said “Phyle gave away the game by distributing bases on balls in just the spots where timely hits followed and transformed the favors into tallies that gave the victory.”
William Phelon, The Chicago Daily News baseball writer, disagreed. He said Phyle’s “work was of sterling quality.”
Regardless, Chicago Manager Tom Burns didn’t give Phyle another opportunity to pitch for more than a month.
Phelon said it was a mistake for Burns to not use Phyle. The Chicago Inter Ocean said after the team lost seven of nine games in May “it is passing strange that young Phyle is not given a chance. On last year’s form Phyle is as good as, if not better than (Jack) Taylor. The paper called Phyle’s performance in the St. Louis game “gilt-edged” and blamed the loss on “comrades that gave the victory to the enemy.”
Finally, on May 28 Phyle pitched again. He lost 4 to 3 to the Washington Senators; he gave up three runs on five straight hits with two outs in the ninth.
He lost again on June 1, 7-1 to the Philadelphia Phillies. Phelon’s opinion of the pitcher was unchanged, and said the losses were simply bad luck:
“Phyle has now lost four straight games. It is Phyle’s luck to be stuck in whenever the other pitchers have won about three straight, and the team is just about unavoidably due to lose.”
On June 5 Phyle did his best pitching of the season–a victory he is not credited with in the record books.
With the Orphans trailing the Baltimore Orioles 3 to 2 in the third inning, pitcher Clark Griffith was ejected for arguing a called ball. The Chicago Tribune said:
“It was a queer game. Phyle pitched after Griffith had been benched…holding the Orioles helpless.”
Chicago won 9 to 4. And while the Chicago newspapers credited the victory to Phyle, the record books do not.
Box score for June 5 game. Phyle relieved Clark Griffith in the 3rd inning.
Phyle became ill later the same week, (some sources said it was recurring malaria), a week later he fell off a bicycle and missed two more weeks. When he returned to the team on June 22, the Boston Beaneaters beat him 5 to 1.
He was credited with his first “official” win on July 1—a game The Inter Ocean called “a comedy of errors,” and a “depressing exhibition.” He beat the New York Giants 10 to 9, allowing 10 hits and giving up seven runs in the first two innings. Each team committed seven errors.
Box score of Bill Phyle’s only “official” victory of 1899.
Chicago went into a slump that would last for the rest of the season; after Phyle’s July 1 win the team was 38-24, in third place, and went 37-49 the rest of the way finishing eighth.
Phyle lost again on July 9 and July 24, and rumors began to circulate that he would be released or traded back to Charlie Comiskey’s St. Paul Saints.
On August 6 Phyle lost 10 to 9 to the Cleveland Spiders. One week later while the team was on the road, The Inter Ocean reported that he “was sent home by manager Burns.”
The Tribune called Phyle “the scapegoat” and said he and three unnamed teammates “celebrated after beating a horse race at Washington and Manager Burns, to call a halt, put the punishment on Phyle.
Phelon wrote in The Daily News:
“When the club started for Philadelphia he was told to go home ‘You are through young man, go back to Chicago,’ said Burns, and Phyle went back. He went back in a rage too, and says he will tell (team president) Jim Hart a lot of things. He says that he has been held up to public derision as a drunkard, all season, and that Burns plays favorites, allowing his friends to jag up as much as they wish and turning all the trouble on others.”
Phelon remained supportive of the pitcher in The Daily News, but in The Sporting Life he reported that Phyle, a former boxer, had deserted the team in early August to go to “St. Louis to see a prize fight, and was not on hand when sorely needed.”
While the relationship between Hart and Burns was strained, and Burns would be replaced at season’s end, Phyle’s complaints went nowhere with the team president and he was suspended without pay.
Ten days after Phyle was suspended Phelon reported that the Baltimore Orioles had offered to trade for or buy Phyle,” (John) McGraw has taken quite a fancy to the young pitcher.” Hart refused to make a deal.
Phyle never pitched for Chicago again, he is credited with a 1-8 record and 4.20 ERA.
The last Bill Phyle chapter—tomorrow.
Baseball History Daily 
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