This is a tough one. Several center and right fielders in Yankee history have also played left field at various times in their careers, including Babe Ruth and Mickey Mantle. I decided to limit this to only players who are best known for playing the position.
That gets harder when you consider that, from 1955 to ’58, the Yankees’ main left fielder was Elston Howard, who was a catcher by trade, but was waiting behind Yogi Berra. In 1959, Yogi’s decline began, although he could still hit, and he and Ellie switched positions. So both Yogi, who remained the starting left fielder until 1962, and Ellie could be among the Top 10 Yankee Left Fielders. But I’ve already included them in the Top 10 Yankee Catchers, so I won’t. That means there’s going to be a big gap from 1955 to 1962, one of the most successful periods in Yankee history.
This also lets out Johnny Damon and, for the moment, Brett Gardner.
Dishonorable Mention to Ben Chapman (1930-36) and Jake Powell (1936-40). Chapman was a member of the 1932 World Champions, a .302 lifetime hitter, a 4-time All-Star, and one of the few base-stealing threats the Yankees had between the 1920 arrival of Babe Ruth and the 1975 return of Billy Martin. But as manager of the Philadelphia Phillies in 1947, he led the most vicious bench-jockeying any athlete has ever received, the noxious racial abuse hurled by the Phils at Jackie Robinson. The backlash got so bad that it was recommended that, when the Dodgers got to Philadelphia, the two men pose for a conciliatory picture. But the Alabama-born Chapman refused to shake hands with Robinson, settling instead for posing with the two of them holding the same bat. The next year, with the Phillies having rising stars like Richie Ashburn and Robin Roberts but still far behind the NL lead, Chapman was fired, and except for a brief tenure as a Reds coach never worked in the game again. Years later, he would admit he had gone too far.
But at least Chapman lived long enough to have, and show, remorse. Powell was, effectively, his replacement as Yankee left fielder, and was a member of the 4 straight World Championship teams of 1936-39. But in 1938, with the Yankees in Chicago, White Sox broadcaster Bob Elson interviewed him for a pregame radio show, and asked Powell what he did in the off-season. The native of the suburbs of Washington, D.C. said he was a police officer in Dayton, Ohio. Asked what he did to keep in shape, Powell told Elson, “Crack (N-word)s over the head with my nightstick.” Even as notorious a racist as Baseball Commissioner Kenesaw Mountain Landis knew this was too much – and probably also cared that it was a bald-face lie – and he suspended Powell for 8 games. Two years later, Powell was out of The Bronx, and was out of the game by 1945. In 1948, arrested for public drunkenness, he grabbed the cop’s gun and shot himself, an ironic end considering what he’s best known for.
10. William “Birdie” Cree, 1908-15. Got his nickname because he liked to whistle. He twice batted over .300 and helped the Highlanders/Yankees finish 2nd in 1910. In 1911, he batted .348 with 30 doubles, 22 triples, 4 homers and 88 RBIs.
9. Tim Raines, 1996-98. Just 3 seasons in Pinstripes, but they were all Playoff seasons, and ’96 and ’98 were World Championship seasons. "Rock" .321 in ’97 and .290 in ’98, despite being 37 and 38 years old in those seasons. In Game 3 of the ’96 Series, led off the game with a walk, and scored on Bernie Williams’ single to give the Yanks their first lead of the Series, and later started a double play; his 2-out walk in the top of the 10th led to his scoring the winning run in Game 4.
Overall for his career, a 7-time All-Star, .294 average, 123 OPS+, 2,605 hits, and a whopping 808 stolen bases, 5th all-time and most of anybody not in the Hall of Fame. Judging by Baseball-Reference.com’s HOF Monitor (90 of 100), HOF Standards (47 of 50), and Top 10 Most Similar Batters (4 of 10 already in), he’s got a very good case.
8. Roy White, 1965-79. First Yankee (or former Yankee) I ever actually met (if you’ll pardon the choice of THAT word), and all the talk about him being classy was an understatement. His timing was bad, arriving just as the old dynasty was collapsing, but he was a 2-time All-Star, led the AL in walks in 1972 and runs in 1976, and finally got to play in 3 World Series, winning 2. His 1st-inning homer in Game 3 of the ’78 Series gave the Yanks their first lead of the Series, and in Game 4 he scored the winning run in the 10th.
He never batted .300, hit 25 homers or had 100 RBIs, although he came close to each. But he won games and he won titles. He wasn’t a headline, but he helped make them. Later became a Yankee coach. His Number 6 will be retired someday, although not for him. But he was the first former player introduced at the old Yankee Stadium finale in 2008, and deservedly got a big hand.
7. Gene Woodling, 1949-54. He was from Akron, Ohio – the first Yankee star to be born there, but not the last – but became the last Yankee star to be purchased from the San Francisco Seals of the Pacific Coast League. He helped the Yankees win the next 5 World Series, batting over .300 in 1952 and ‘53. Not that anybody knew it at the time, but he led the AL in on-base percentage in ’53, .429. He bobbled what should have been the last out of the 1950 Series, costing rookie Whitey Ford a shutout, but in a far tighter situation (ahead by 2 with the winning run at the plate in Game 7, as opposed to the earlier 5-run lead in a sweep-clincher), caught the last out of the ’52 Series.
The Yankees including him in the biggest trade in baseball history, the 18-player deal with the Baltimore Orioles after the ’54 season that brought in 2 pitchers who would make their mark in Pinstripe history, Don Larsen (still the only man to pitch a no-hitter in the World Series) and Bob Turley (first Yankee to win the Cy Young Award). It was with the O’s that he reached his only All-Star Game, in ’59. (A guy named Ted Williams being in the AL and having the one subpar year of his career in ’59 had something to do with that.)
6. Tom Tresh, 1961-69. Had a cup of coffee with the M&M Boys’ Yankees, then was the AL Rookie of the Year in 1962, playing shortstop while Tony Kubek was spending most of the season in the Army. Moved to the outfield when Kubek came back, and, depending on how big the field was in a ballpark and how much Mickey Mantle’s legs were bothering him, spent much of the next 4 seasons switching between left and center with Mickey. An All-Star in ’62 and ’63 and a Gold Glove in ’65, his homer won Game 5 of the ’62 Series, and his homer in Game 1 of ’63 broke up a no-hitter by Sandy Koufax (though it didn’t stop Koufax from fanning 15, then a Series record and still a Series record for lefties).
Never batted .300 or had 100 RBIs, but topped 20 homers 4 times – and, like Mantle, was a switch-hitter, so he wasn’t just taking advantage of the pre-renovation Stadium’s short RF porch, and in fact was hurt by its LF and CF Death Valley. Grew up outside Detroit, where his father Mike Tresh grew up; unlike his father, who played mostly for the White Sox, finished his career with their hometown Tigers. His own son, Mickey (named for Mantle), was a Yankee farmhand, but never got past Double-A ball.
5. Lou Piniella, 1974-84. The 1969 AL Rookie of the Year with the Kansas City Royals, he didn’t get along with management there, so they sent him to the Yankees for lefty reliever Lindy McDaniel. Great trade for both teams. McDaniel was washed up, but he was practically an extra pitching coach for the Royals’ young staff. Piniella, well, let’s just say he was called “Sweet Lou” not for his disposition, but for his swing.
At first he played mostly right field, with White in left. By the time Reggie Jackson arrived for 1977, White was mostly a bench player and Lou was the main man in left, and he became a pretty good left fielder, his catch taking a home run away from Ron Cey of the Dodgers in Game 4 of the World Series. In the 1978 Playoff with the Red Sox, Reggie was the DH, Roy was in left and Lou in right, and he made 2 key plays in that game to save it.
And what a hitter: .291 lifetime average, 109 OPS+, 6 .300 seasons (4 with the Yankees), and always seemed to come through in key situations. As a boy, I enjoyed Nathan Salant’s book This Day In Yankee History, and as he wrote of the 1978 “Boston Massacre” series, he mentioned that Reggie had been intentionally walked: “That made no sense at all, because the next batter was the Red Sox killer himself, Lou Piniella.” And Piniella went 10-for-16 with 5 RBIs in that series. He also batted .305 with 2 homers and 6 RBIs in his 5 ALCS appearances and .319 with 10 RBIs (albeit none on homers) in his 4 World Series. If it was October, and Lou was batting against you, you were not thinking it was sweet.
He retired and became the Yankees’ hitting instructor, then, except for a brief 5th term for Billy Martin, was the Yankees’ manager from 1985 to ’88, getting them in the AL East 4 straight seasons but never getting that one extra starting pitcher he needed from George Steinbrenner. He helped make Don Mattingly a great hitter, but had to go to the Cincinnati Reds – where he helped make Paul O’Neill a great hitter, if one with a similarly explosive temper – to win a Pennant and a World Series as a manager. He remains the only manager to lead the Seattle Mariners to a postseason berth, 4 of them. It’s unlikely the Number 14 he wore as a Yankee will be retired anytime soon, but Lou was a classic Yankee, and one of my 5 favorite players of my time.
4. Bob Meusel, 1920-29. “Long Bob” and his brother Emil (known as Irish even though the family was of German descent) were among the earliest Californians to reach the majors – or, as the people involved in or rooting for teams in the Pacific Coast League said until 1957, “the eastern leagues.” Both went to New York, Irish to the Giants, Bob to the Yankees, and they opposed each other in 3 straight World Series, the Giants winning in 1921 and ’22, the Yankees in ’23. Bob also helped the Yankees win the ’26 Pennant and the ’27 and ’28 World Series.
He was a lifetime .318 hitter, who was a perfect fit in the Yankee lineup, 5th after Babe Ruth batted 3rd and Lou Gehrig 4th – hence, in his last full season, 1929, the first season in which the Yankees wore uniform numbers, Meusel was the first to wear the Number 5 that would be solely identified with Joe DiMaggio (who, of course, did not always bat 5th). Five times, Meusel drove in at least 100 runs, and led the AL in homers and RBIs in 1925. He played with the Cincinnati Reds in 1930, then headed back west and ended his career in the PCL. He died in 1977, at age 81.
3. Charlie Keller, 1939-49, with a brief return in ‘52. He was big and strong and hairy, and they called him King Kong – though not to his face, as he hated the nickname. This guy formed one of the greatest outfielders ever, with Joe DiMaggio in center and Tommy Henrich in right. His best known hit was a double off the right-field wall at Ebbets Field to complete the rally after Mickey Owen’s muff kept the Yanks alive in Game 4 of the 1941 World Series. He was hitting at a Hall of Fame pace, averaging a .296 batting average, 24 homers and 98 RBIs in his first 5 seasons, 4 of which ended with Yankee Pennants (1939, ’41, ’42 and ’43) and 3 with World Series wins (all but ’42).
Then he went off to war, and when he got back a back injury slowed him down. He helped the Yankees win a 4th and 5th Series in ’47 and ’49, but that was pretty much it for him: His last great year was at age 29, and he packed it in at 35. He returned to his native Maryland and trained racehorses at his Yankeeland Ranch, many of them with "Yankee" in their names.
2. Hideki Matsui, 2003-09. His first home game at a Yankee Stadium, he hit an Opening Day grand slam. His last home game at a Yankee Stadium, he went 3-for-4 with a homer and 6 RBIs to clinch a World Championship. In between he gave us a bunch of memories, including one of the 4 straight hits off Pedro Martinez in 2003 ALCS Game 7, maybe the best game ever played at the old Stadium.
He's with the Oakland Athletics now, and new catcher Russell Martin may end up getting his Number 55. But "Godzilla" was a beast. I wonder if he'll be the first Yankee to get a Plaque with part of its next not in English?
1. Dave Winfield, 1981-90. In the strictest sense, Big Dave was the Yankees’ main left fielder for only 3 seasons, 1981, ’82 and ’83, before moving over to right field. (Steve Kemp was the main one in ’84, Ken Griffey Sr. in ’85, Dan Pasqua in ’86, Gary Ward in ’87, Rickey Henderson moving from center to left for ’88, then Mel Hall taking over after Rickey was traded in ’89.)
Big Dave went 1-for-21 in the 1981 World Series, and that led George Steinbrenner to eventually call him "Mr. May." It was totally unfair, and even less fair was how George got rid of him -- which led to baseball temporarily getting rid of George, and Dave getting the hit that clinched the 1992 Series for the Toronto Blue Jays.
He hit 465 home runs, got over 3,000 hits, is in the Hall of Fame, and had most of his great years with the Yankees. Yet his Number 31 has been continually given out (sometimes it's worked, as with the aforementioned Tim Raines; sometimes not, as with several weak pitchers), and he hasn't gotten his Monument Park Plaque. No ring? Don Mattingly has a Plaque but no ring, and he was not a better player than Winfield. The ovations Dave gets when he comes back for Old-Timers' Day are not enough: Hank, Hal, give him his Plaque! And don't ever let another kid just off the Columbus -- excuse me, Scranton -- Shuttle sully his 31!
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