Right-hander Ray Caldwell joined the Highlanders in 1910, when his contract was purchased from McKeesport of the Pennsylvania League.
After a late-season cameo in 1910, Caldwell slotted into the Highlanders’ rotation in 1911, posting a 3.35 ERA and 1.251 WHIP while going 14-14 in 41 appearances, 26 of them starts, and 255 innings with 145 strikeouts.
He struggled in 1912, working 183.1 innings in 30 games, 26 of them starts, while going 8-16 with a 4.47 ERA and 1.435 WHIP for a team that finished 50-102.
Caldwell stabilized in 1913 despite missing time with a sore arm, with a 2.41 ERA and 1.162 WHIP in 164.1 innings.
He had his best season with New York in 1914, going 18-9 with a 1.84 ERA and 0.958 WHIP in 213 innings and became the workhorse of the staff in 1915, throwing a career-high 305 innings while going 19-16 with a 2.89 ERA and 1.223 WHIP.
Per SABR, his career was hampered by his affinity for the New York nightlife and in December 1918, the Yankees traded Caldwell to the Boston Red Sox in a seven-player deal.
In nine seasons in New York, Caldwell was 96-99 with a 3.00 ERA and 1.219 WHIP, striking out 803 hitters in 1,718.1 innings. But he could also swing the bat, being used occasionally as an outfielder and first baseman and often as a pinch-hitter.
He hit .250/300/.323 in 1,033 career player appearances for New York, with seven homers, 34 doubles and 98 RBI, while stealing 23 bases.
Caldwell would later pitch for the Cleveland Indians before fading to the minor leagues after the 1921 season. While he pitched professionally from 1910-33, only 12 of those seasons were in the bigs.
He died Aug. 17, 1967, in Salamanca, New York at the age of 79.