1914
After being swept by the Boston Braves in the World Series, Philadelphia A's owner/manager Connie Mack decided to liquidate his roster, releasing two of his best pitchers--Chief Bender and Eddie Plank (Hall of Famers both). Mack then proceeded to target his coveted "$100,000 Infield," sending Cooperstown-bound second baseman Eddie Collins to the White Sox. Frank "Home Run" Baker, Mack's star third baseman, (who would eventually join Collins in Cooperstown) opted to sit out the 1915 campaign on the heels of a bitter salary dispute. Other disastrous transactions would follow, including the loss of sure-handed shortstop Jack Barry. As a result, the A's wallowed in the American League basement for seven straight seasons.
1916
Although the rise of Babe Ruth helped fans forget, the Red Sox made a huge mistake when they traded Hall of Fame center fielder Tris Speaker to Cleveland during the spring of 1916. Speaker had won an MVP Award (then known as the Chalmers Award) with Boston in 1912 and was still very much in his prime. In his first season with the Indians, he led the American League in hits, doubles, batting average, on-base percentage and slugging percentage. He spent eleven years in Cleveland altogether, compiling a cumulative .354 batting average while helping the Indians to the first championship in franchise history (during the 1920 slate).
1919-1923
Nearly everyone has heard about Red Sox owner Harry Frazee's misguided sale of Babe Ruth to the Yankees before the 1920 campaign. But Ruth was not the only player that Frazee cast aside to keep his business interests afloat. In July of 1919, he allowed temperamental pitcher Carl Mays to jump to the Yankees, provoking the ire of AL President Ban Johnson in the process. In 1921, Frazee sent catcher Wally Schang and Hall of Fame pitcher Waite Hoyt to the Bronx. In 1922, he added Sad Sam Jones and Bullet Joe Bush to the Yankee rotation. Shoring up the Yankee infield, he included marquis shortstop Everett Scott in the deal. Midway through the '22 campaign, Frazee sent third baseman "Jumpin' Joe" Dugan to New York as well. And then, completing a series of ridiculously generous transactions, the impulsive Red Sox owner donated Hall of Fame moundsman Herb Pennock to the Yankee cause in 1923. The BoSox sank like a stone while the Yankees, making the most of their acquisitions, appeared in three consecutive World Series from 1921-1923.
1925
It wasn't like Giants manager John McGraw to miss the boat when it came to spotting talent. But his roster was so cluttered with stars already, he traded twenty-five year old center fielder Hack Wilson to Toledo of the American Association in September of 1925. Wilson forged a Hall of Fame career mostly with the Cubs, packing his best seasons into a seven-year span from 1926 through 1932. He averaged 30 homers and 127 RBIs per year in that stretch. His 191 runs-batted-in during the '33 slate are still an all time record.
1926-1929
Rogers Hornsby had a lot of undesirable traits. He was mean and prickly. He tended to alienate teammates and engage in salary disputes with owners. Still, it's hard to believe that baseball's greatest second baseman was traded as often as he was. Hornsby began his career in St. Louis, where he won six straight batting titles. After the 1926 campaign, he was dealt to the Giants. He hit .361 in New York while scoring a league-high 133 runs. The following year, he was shipped to Boston, where he won a batting crown and led the NL with a superhuman .498 on-base percentage. His travels continued in '29 as he hit .380 for the Cubs while pacing the circuit with 409 total bases. The Cubs were smart enough to hang onto him until his skills went into decline. To date, Hornsby's lifetime batting average is the second highest of all time behind Ty Cobb.
1935
Connie Mack was faced with some tough decisions during his fifty years at the helm of the A's. With his team in decline and the Great Depression putting the squeeze on him, he was forced to part with his best offensive player before the '36 campaign. First baseman Jimmie Foxx, winner of consecutive MVP Awards in '32/'33, had several more phenomenal seasons after leaving Philadelphia, narrowly missing a second triple crown with the Red Sox in 1938. Though Foxx's lifetime total of 534 homers has been surpassed by several players, he was second on the all time list when he retired.
1974-1977
During the 1970s, the A's became the first team outside New York to win three consecutive World Series titles. A's owner Charlie Finley--among the most tight-fisted executives in baseball history--began dishing off most of his high-priced players shortly afterward. Catfish Hunter was the first to go, signing with the Yankees for the '75 campaign. Reggie Jackson was the next in line, defecting to Baltimore in '76. With free agency in full swing, Finley attempted a full scale roster purge, trading closer Rollie Fingers and outfielder Joe Rudi to the Red Sox in June of '76. On the same day, he dealt staff ace Vida Blue to the Yankees. Baseball Commissioner Bowie Kuhn voided both deals, citing that Finley's fire sale was "not in the best interest of baseball." Rudi and Fingers left after the '76 slate anyway. Finley tried to get rid of Blue again the following year, trading him to the Reds, but Kuhn intervened a second time, commenting that the deal would tip the balance of the NL West. Determined to part ways with his star southpaw (who had averaged 17 wins per season between '71 and '77), Finley sent Blue to the San Francisco Giants before the '78 slate. By then, every starting player from the '74 championship squad (with the exception of outfielder Bill North) was gone.
1980
Dave Winfield began his career with San Diego, slowly emerging as one of the premier outfielders in the National League. After four consecutive All-Star appearances, the Padres granted him free agency. The blockbuster contract Winfield signed with the Yankees in 1980 made him the highest paid player in baseball. For nearly a decade, he lived up to expectations, getting named to eight All-Star teams while adding five Gold Gloves to his collection. But tempestuous Yankee owner George Steinbrenner didn't like Winfield. In the wake of a World Series defeat in '81, he referred to Winfield as "Mr. May"--a derogatory comparison to slugger Reggie Jackson, who had earned the prestigious title of "Mr. October" for his World Series heroics with the Yankees. After Winfield sued the club for failing to contribute to a charity bearing his name (a stipulation of his contract), Steinbrenner hired gambler Howard Spira to dig up "dirt" on the high-priced outfielder. When Commissioner Fay Vincent found out, he banned Steinbrenner from day-to-day management of the Yankees. Winfield later requested that he be enshrined at Cooperstown as a member of the Padres. He became the first San Diego player to make it to the Hall.
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