The first winter trade in the history of the New York Yankees came back in December, 1903 when they were still called the Highlanders. Its parameters should be familiar, as they stink vaguely of Ed Whitson/Kenny Rogers/Carl Pavano and other mistakenly acquired hurlers. The Highlanders—I’m going to call them "Yankees" from now on, because that’s easier—had acquired a left-handed starter named Jesse Tannehill from the Pittsburgh Pirates. Just as "Yankees" isn’t quite accurate, "acquired" also doesn’t quite do the situation justice. In those days of war between the American and National Leagues, when the two circuits had yet to merge into one happy company, contracts were not respected. Players flew back and forth between the junior and senior circuit at the beck and call of the highest bidder. Tannehill was one who heeded the siren song of the Yankee greenback dollar.
This was a seeming coup for the New Yorkers. Tannehill was a little guy (5’8"), and pitchers, even over 100 years ago, were always big guys. But the lefty had a mesmerizing slow curve and great self-confidence. In six seasons with the Pirates, the pitcher went 116-58 with a 2.75 ERA, which was just as good then as it is now. He had excellent control, walking just 1.5 batters per nine innings. With the dead ball working in his favor, batters just didn’t take him deep—from 1901-1902, he pitched 483.1 innings and allowed just one homer, and you can bet that was an inside-the-parker.
According to SABR’s biography of Tannehill, the southpaw and several of his teammates were offered $1000 bonuses (read: bribes) from American League president Ban Johnson to jump to New York. Tannehill took the offer, bringing, among others, Jack Chesbro with him, but not before a scuffle with teammates, possibly over his impending defection, caused his pitching arm to be dislocated. The disappointing quality of Tannehill’s Yankees career should therefore not have been surprising. He went 15-15 with a 3.27 ERA in 1903, which was below average for the time. He disliked Hilltop Park; it was too cold. He disliked manager Clark Griffith. For all we know, he disliked cuddly Wee Willie Keeler (who probably wasn’t all that cuddly and actually smelled of chewing tobacco, stale beer, and old socks).
Thus, the second winter trade in the history of the New York Yankees was to swap Tannehill away, to the Boston Red Sox (even before Harry Frazee the two clubs were making deals) for a right-handed pitcher named Long Tom Hughes, who was three inches taller (that seems to be what the "Long" referred to—get your mind out of the gutter, people) and had just gone 20-7 with a 2.57 ERA, neither quite as good as they look to our eyes today, but not bad either. Naturally, Hughes fell apart in New York, going 7-11 with a 3.70 ERA, said ERA being terrible for that time and place, like a 6.50 today. He was dealt away to Washington at midseason for yet another pitcher, a righty named Al Orth. Orth pitched to a league-average ERA in six seasons and was sometimes better, so the Tannehill merry-go-round finally landed in a good place.
As for the first good winter trade in Yankees history, I’m inclined to say it was the December, 1906 purchase of Branch Rickey. Sure, Rickey hit only .182/.253/.234, but how can association with Rickey be considered a bad thing? For the true first/best winter deal in team history, we have to go to the expected place: January 3, 1920 and a little swap that sent a few dollars north to Boston for a pitcher-outfielder named Babe Ruth.
And all of this is my way of saying that we’re still waiting for the first Yankees deal of this winter.