Derek Jeter and MLB's 30 All-Time Toughest Career Endings to Watch
There has been much talk about the declining skills of New York Yankees shortstop Derek Jeter over the past season plus—last year hitting .270, a full 43 points below his career average of .313, and his .257 average this year with just nine extra base hits. Jeter is chasing the magical 3,000 hit mark, and will likely reach that mark before the All-Star break, with just 21 hits needed. However, is Jeter playing out the string? Have has skills diminished to the point that he is no longer useful to his beloved Yankees?
The history is MLB is literally littered (pardon the pun) with players who believed they could still make valuable contributions to their teams, in spite of their bodies and deteriorating skills telling them otherwise.
The image of an overweight Babe Ruth struggling through his last season with the Boston Braves is a telling example. Ruth, long stripped of his prodigious home run mastery, was clearly overmatched when he stepped onto the baseball fields in that last season in 1935.
It’s difficult for ballplayers to look inside themselves and determine that they just can’t cut it any longer. The lure of big contracts, fame, and their love of competition often gets in the way of making an informed decision regarding the end of their careers.
On May 29, 1989, the great third baseman Mike Schmidt acknowledged that decision when he decided, saying "I could ask the Phillies to keep me on to add to my statistics, but my love for the game won't let me do that." Schmidt, hitting .203 at that point, obviously realized he couldn’t contribute at a high level any longer.
In any event, there are a number of players who hung around in baseball far longer than they should have. Many of those players had already cemented their status in baseball’s Hall of Fame, but continued on in vein.
Here then is a list of 30 players who should have ended their careers in Major League Baseball far earlier than they did.
Source: Baseball Almanac
Doug Mead is a featured columnist with Bleacher Report. His work has been featured on the Seattle Post-Intelligencer, SF Gate, CBS Sports, the Los Angeles Times and the Houston Chronicle. Follow Doug on Twitter, @Sports_A_Holic.
30. Carlton Fisk: 1969, 1971-1993
Catcher Carlton Fisk played the most demanding position in baseball for 24 seasons, playing in 2,226 games behind the plate, good for second place all-time behind Ivan Rodriguez. Fisk is also second all-time in total home runs as a catcher with 351, trailing only Mike Piazza (396).
However, for Fisk’s last two seasons, he was essentially a part-time catcher who could no longer hit. Fisk hit .229 and .189 respectively in 1992 and 1993.
Fisk hung around specifically to break Bob Boone’s record for career games caught. Six days after he broke Boone’s record, Fisk was released by the Chicago White Sox in a controversial move that shed light on Fisk’s testy relationship with White Sox owner Jerry Reinsdorf.
29. Jim Rice: 1974-1989
Boston Red Sox left fielder Jim Rice was considered of the most feared right-handed hitters in the majors in the late 1970s-early 1980s. Rice put together one of the memorable seasons ever for a right-handed hitter in 1978, collecting 213 hits, 46 home runs, 139 RBI, a .315 average, a .600 slugging percentage and 406 total bases, the most in the American League since Joe DiMaggio totaled 418 total bases in 1937.
However, after the 1986 season, during which Rice helped lead the Red Sox to the World Series with 20 HR and 110 RBI, hitting .324, his numbers across the board dramatically declined, and Rice finally called it quits in August, 1989, after hitting just .231 with just three homers.
Ironically, Rice was not voted into the Hall of Fame until his 15th and final year of eligibility in 2009, with many writers pointing to the fact that his career faded at an earlier age.
28. Luis Castillo: 1996-?
Second baseman Luis Castillo enjoyed a good, steady career as a second baseman, winning three Gold Glove awards and being selected to three All-Star teams. A .290 hitter throughout his career, Castillo was a pesky hitter as well.
However, during Castillo’s career in New York, he was dogged by a spate of injuries, and periods of time that saw him benched. While he enjoyed a nice season in 2009, the following year was a disaster, as Castillo fell out of favor with both fans and management.
Castillo was finally released by the Mets in spring training this year, eating his entire salary of $6 million for the 2011 season. While the Philadelphia Phillies gave Castillo a brief nine-day look late in spring training before releasing him, no other team has contacted Castillo since.
27. Randy Johnson: 1988-2009
Randy Johnson essentially played the last three seasons for one reason and one reason only—to reach the 300-win mark for his career. And he found suckers, er teams, more than willing to overpay him for a roster spot.
In January 2007, the New York Yankees traded Johnson along with cash to the Arizona Diamondbacks, the same team that Johnson helped in beating the Yankees for the 2001 World Series championship, for four players. Johnson was paid $24 million for his two seasons in Arizona, during which he won fifteen games and missed a major chunk of the 2008 season to back issues.
In 2009, Johnson found another sucker, er team, the San Francisco Giants, willing to pay him $8 million so he could reach the 300-win plateau. Johnson reached the mark on June 4, and won only three games the rest of the season.
Johnson was already a lock for the Hall of Fame before 2007, having won 280 games and five Cy Young awards overall.
26. Jim Kaat: 1959-1983
Jim Kaat pitched for 25 seasons in the majors, the third longest career for a pitcher in history behind Tommy John and Nolan Ryan. Arguably, Kaat’s career was at least three years too long.
Kaat spent the last five seasons of his career as a reliever, picking up just 22 victories during that time, and never even coming close to his career ERA+ plus of 108. Kaat finally, mercifully, retired in July 1983 at the age of 44.
25. Al Kaline: 1953-1974
Between the years of 1955-1967, Detroit Tigers right fielder Al Kaline was elected to the All-Star team every season and won Gold Glove awards in 10 of those 13 seasons. In 1968, Kaline returned after suffering a broken arm and helped the Tigers win their first World Series championship since 1945.
However, after the 1968 season, Kaline was a shell of a player he once was, matching his career batting average (.297) only once in his last six seasons (1972, .313).
While Kaline is undoubtedly one of the best players ever to wear a Tiger uniform, his ending wasn’t anywhere near his glory years.
24. Jorge Posada: 1995-Present
At 39 years of age, New York Yankees catcher Jorge Posada is now the designated hitter for the Bronx Bombers, and to say he has struggled in that role is putting it mildly.
Currently sporting an average of .174 with just 11 extra base hits in 41 games, Posada has clearly shown he is now overmatched at the plate.
Along with Mariano Rivera and Derek Jeter, Posada joins a trio of players who have played for the same organization for 17 years, an all-time record for three players with one team.
Could it be the 17th season was one year too long?
23. Fred McGriff: 1986-2004
First baseman/designated hitter enjoyed a great 19-year career in the majors, and although he tried mightily to reach the hallowed grounds of the 500-home run club, McGriff fell seven homers short.
During McGriff’s last two seasons during which he was chasing that elusive mark, he was nowhere near the player that slugged 30 home runs 10 times during his career.
McGriff was finally released by his hometown Tampa Bay Devil Rays after 27 games in 2004, during which McGriff hit just .181 with two home runs.
Hanging on for a record is one thing. But costing your team a valuable roster spot is another entirely.
22. Tom Glavine: 1987-2008
The next stop that Tom Glavine will make in baseball is the Hall of Fame, there is no doubt about that. In 2007, Glavine, who is a two-time Cy Young award winner and five-time 20-game winner, won his 300th game pitching for the New York Mets.
In 2008, Glavine signed a one-year contract to return to the Atlanta Braves, the team where Glavine gained his fame. However, he only won two games and was placed on the disabled list twice, the only time during his 22-year career that had ever happened.
Glavine signed another one-year deal with the Braves the following season, Glavine was released by the Braves in June of 2009, after trying to complete a rehab assignment.
I understand Glavine wanting to return to where he was beloved and where he achieved most of his acclaim during his career. But after two wins and an inglorious break-up with the Braves, was it really worth it?
21. Nolan Ryan: 1966, 1968-1993
Nolan Ryan set a record for longevity that may never be matched, pitching 27 seasons across four decades. However, Ryan should have called it a career after 25.
In Ryan’s last two seasons, he was 10-14 with a 4.46 ERA, almost a run and a half higher than his career ERA of 3.19. He had nothing left to achieve, having already notched seven no-hitters and well ahead of Randy Johnson as the all-time leader in strikeouts.
Then again, we never would have seen the famous fight with Robin Ventura.
20. Lefty Gomez: 1930-1943
During the 1930s, Lefty Gomez was the ace of the New York Yankees pitching staff, winning 20 games four times and selected to the All-Star team four times. Gomez was instrumental in helping to lead the Yankees to five World Series championships during the 1930s as well.
However, in 1940 Gomez suffered a devastating arm injury, limiting him to a 3-3 record that season. The following year, Gomez won 15 games, however was unable to go deep into many games, registering only eight complete games, by far his lowest total as a starting pitcher.
Gomez won six games the following season and was sold by the Yankees to the Boston Braves in January 1943.
Gomez never pitched for the Braves and never won another game, retiring at the end of the 1943 season.
19. Dizzy Dean: 1930, 1932-1941, 1947
Dizzy Dean pitched for the famous Gashouse Gang St. Louis Cardinals’ teams of the early-to-mid 1930s and became the most feared right-handed pitcher in the majors, becoming the last pitcher in the National League to win 30 games in a season in 1934.
That season, together with his brother Paul, they won 45 games overall, a record for most wins by brothers in the same season that still stands.
In the All-Star game in 1937, Dean was pitching to Cleveland Indians’ center fielder Earl Averill. Averill hit a hard comebacker to the mound, breaking Dean’s left big toe.
Dean rushed back from the injury, and as a result changed his throwing motion to avoid landing hard on his injured toe. The change in his throwing motion hurt his arm, and the famous Dean fastball was lost forever.
Dean continued trying to pitch, signing a contract with the Chicago Cubs in 1938. While he did help the Cubs into the World Series, Dean only pitched in 13 games that season and won only nine games in the next three seasons before finally calling it quits in 1941.
Dean did make one more appearance as a pitcher, in a marketing ploy for the St. Louis Browns in September 1947.
18. Dave Dravecky: 1982-1989
In the early-to-mid 1980s, Dave Dravecky was a very effective pitcher for the San Diego Padres, effective as both a starter and out of the bullpen, and was an integral part of the Padres team that won the National League pennant in 1984.
In July 1987, Dravecky was involved in a trade that sent him to the San Francisco Giants to help them during the pennant drive. Dravecky did indeed help the Giants to the postseason, posting a 7-5 record and 3.20 ERA in 18 starts.
However, the following season, Dravecky was injured early and often, and after the season ended, Dravecky was diagnosed with a cancerous tumor in his pitching arm. After rehabbing for most of the following season, Dravecky made a successful return on Aug. 10, 1989, pitching eight innings and earning a victory over the Cincinnati Reds.
However, five days later, in a game against the Montreal Expos, Dravecky made a pitch in the sixth inning and immediately fell to the ground in obvious pain. Dravecky had snapped his humerus bone, the same bone that had been affected by the cancerous cells.
Dravecky later found out the cancer had returned, forcing his retirement, and two years later, Dravecky’s left arm and shoulder were amputated.
A tragic ending indeed, however Dravecky never should have been allowed to even attempt a return to baseball.
17. Charlie Gehringer: 1924-1942
Detroit Tigers second baseman is largely considered to be one of the greatest second baseman to ever play the game, leading the Tigers to back-to-back American League pennants in 1934 & 1935, winning the series in ’35.
The Tigers were AL champs again in 1940, with a 37-year-old Gehringer helping to lead the way with a .313.
Gehringer should have stopped there, however. In 1941, his age had clearly caught up with him, with his average dipping almost 100 points to .220, and the following year, 1942, Gehringer lost his second baseman’s job to Billy Hancock, hitting just .267 in 45 games.
16. Jeff Bagwell: 1991- 2005
Houston Astros first baseman became part of one of the worst trades in Boston Red Sox, when he was traded by the Red Sox to the Astros in August 1990 for reliever Larry Anderson.
Anderson was expected to help out the Red Sox bullpen for their pennant drive, and Bagwell was then just a prospect playing Double-A ball.
Of course, Bagwell went on to become the National League Rookie of the Year the following season, and in 1994 was voted the National League MVP award as well.
Bagwell was one of the dominant right-handed hitters in the National League in the 1990s and early 2000s, however in 2001, Bagwell developed an arthritic condition that slowly wore away at his shoulder, and by 2004, Bagwell could barely throw the ball across the field to third base, shot-putting the ball rather than throwing it.
In 2005, Bagwell was a complete defensive liability, and only played in 39 games, hitting a full 47 points below his career average of .297 with just three home runs. While Bagwell attempted to play in spring training of 2006, he himself determined he could no longer play every day and wound up retiring.
While Bagwell, was undoubtedly a great player, his teammates admitted that they covered for him defensively during the final two years of his career.
15. Robbie Alomar: 1988-2004
For fifteen seasons, second baseman Robbie Alomar was widely considered to be one of the top second baseman of his generation, winning 10 Gold Glove awards and being selected to 11 consecutive All-Star teams.
However, in 2003 Alomar’s game literally disintegrated, both offensively and defensively. Alomar switched teams four times in his last two years, never once re-capturing the solid play that had defined his career.
After a tryout with the Tampa Bay Devil Rays in 2005, Alomar finally decided to retire. Too bad he didn’t come to that realization two years earlier.
14. Mo Vaughn: 1991-2003
In the early 1990s, Boston Red Sox first baseman had developed into a powerful slugger, winning the American League MVP award in 1995. After three more productive seasons in Boston, Vaughn signed a free-agent contract with the Anaheim Angels, and despite a rash of injuries was still productive when he played.
However, Vaughn missed the entire 2001 season due to injury, and the New York Mets decided to take a chance and worked a trade to bring Vaughn to the Mets for pitcher Kevin Appier.
The trade turned out to be the ultimate downfall for Mets’ GM Steve Phillips. Vaughn did hit 26 homers in his first season in New York, however he was a full 25-30 pounds heavier than his normal playing weight and was the brunt of jokes throughout the New York media.
The following season, 2003, Vaughn only played in 27 games before a knee injury finally ended his career.
13. Gaylord Perry: 1961-1983
Throughout his career in the major leagues, pitcher Gaylord Perry was the true definition of a junk-ball pitcher, and at times even added a little more than that. A two-time Cy Young award winner, Perry was very good for a very long time.
But Perry’s last three years were far from memorable. Perry was 25-35 with an ERA a full run and a half higher than his career 3.11, pitching for three different teams during that span.
12. Tommy John: 1963-1989
While Tommy John is mostly known for the groundbreaking surgery performed on his left elbow by Dr. Frank Jobe in 1974 that widely became known as Tommy John surgery, he is also known as a man who didn’t know when to stop, and his career, while certainly lengthened by his surgery, should have ended five years earlier than it did.
From 1985-1989, John was 33-34 with a 4.45 ERA, well above his career ERA of 3.34 and WHIP of 1.484.
Surgery is great to extend a career, but ending a career in mediocrity is probably not the desired end result.
11. Ken Griffey Jr.: 1989-2010
It was very nice of the Seattle Mariners to bring Ken Griffey Jr. back to the place where it all began for him back in 1989, however the Mariners should have passed.
Griffey had already gone through several years that had completely worn down his body due to damaging injuries. Between 2001 and 2004 alone, Griffey missed 317 games, amounting to two full seasons.
By the time 2009 rolled around for Griffey, he was already 39, beaten up, and just a shell of the great player that had already amassed 611 home runs, 13 All-Star selections, 10 consecutive Gold Glove awards and an MVP award in 1997.
Nice gesture by the Mariners, but a waste of time and money.
10. Tom Seaver: 1967-1986
As great a pitcher as Tom “Terrific” Seaver was, he was done after the 1981 season, during which he went 14-2 for the Reds, and coincidentally, was the last time he made the All-Star team or garnered any Cy Young award votes.
In the last five years of his career, Seaver was 52-62 with a 4.08 ERA, inflating an ERA that had been about 2.50 during the height of his career. Seaver’s inclusion into the Hall of Fame was already a foregone conclusion before the 1981 season.
During the late 1960s and throughout the 1970s, Seaver was one of the most dominant pitchers. During the 1980s? Not so much.
9. Ozzie Smith: 1978-1996
Ozzie Smith was the named “The Wizard” for one specific reason—there was no better defensive shortstop in the history of baseball. Smith won 13 consecutive Gold Glove awards between 1980-1992 and was selected to the All-Star team 15 times during his career.
However, in 1995, Smith suffered a serious shoulder injury that caused him to miss three months of the season, and the following season, 1996, Smith learned from new manager Tony LaRussa that he was being replaced at shortstop by Royce Clayton.
The relationship between LaRussa and Smith is still frosty to this day, and Smith retired at year’s end after missing the first month with a hamstring injury and playing in half his team’s games.
8. Sammy Sosa: 1989-2005, 2007
Together with Mark McGwire, Chicago Cubs right fielder Sammy Sosa helped to rejuvenate baseball in 1998 with their famous chase of the all-time single season home run record set by Roger Maris in 1961. While Sosa eventually lost out to McGwire, Sosa went on to record three 60-HR seasons, the only player in Major League ever to do so.
However, in 2004, Sosa was on the disabled list with back issues and only registered 35 homers with a .253 average, far below his career numbers. Sosa left the Cubs in controversy at the end of the season after he had requested to sit out the last game of the season, and leaving Wrigley Field in the middle of the game.
Sosa was traded by the Cubs to the Baltimore Orioles, but in 2005 Sosa suffered through what was easily the worst year of his career, hitting just .221 with 14 home runs.
Sosa sat out the 2006 season before returning to play in 2007 for the Texas Rangers, where he hit 21 homers with a .252 average. The image of Sosa in those later years with the Rangers and Orioles was a far cry from the image seen during the mid-to-late 1990s when Sosa performed his signature home run hop with regularity.
7. Pete Rose: 1963-1986
Baseball’s all-time hits leader hung around specifically to do just that—become baseball’s all-time hits leader.
Rose’s last good year came in 1982, when at the age of 41, Rose hit .271 with 172 hits, giving him 3,869 hits for his career—good enough for second place on the all-time list behind Ty Cobb.
But Rose wanted that hits record, despite advancing age and diminished skills. So he marched on, becoming a singles hitter for the remainder of his career. Rose was never much of a home run hitter, but he hit exactly two in his final four seasons, and of his final 387 hits, only 60 were extra base hits.
During Rose’s career, almost 25 percent of his total hits went for extra bases—during his last four seasons, only 16 percent.
6. Hank Aaron: 1954-1976
The image of Hank Aaron knocking a pitch by Los Angeles Dodgers’ starting pitcher Al Downing into the left field bullpen on April 8, 1974 is a memory that will live on forever.
On that day, with that swing, Aaron broke Babe Ruth’s all-time career home run record, despite death threats and racial undertones.
Aaron should have retired on that day. While he went on to hit 40 more home runs, it took three seasons. Aaron was a Brave for his entire career, and watching him play his last two seasons as a member of the Milwaukee Brewers not only didn’t look right, it was painful to watch.
Aaron hit .234 and .229 in his final two seasons, relegated to a part-time role as a designated hitter who painfully just could not hit any longer.
5. Manny Ramirez: 1993-2011
The last three seasons of Manny Ramirez’ career were marked by a series of bad choices, bad memories and overall bad vibes. Manny being Manny became a tired old act, and his own undoing was the cause.
Manny became one of the most feared right-handed hitters in baseball history during the 1990s and 2000s, first with the Cleveland Indians and then with the Boston Red Sox, helping to lead the Sox to two World Series championships in 2004 and 2007.
However, the Red Sox finally had had enough of the Manny act, and after Manny had thrown a 60-something year old traveling secretary down to the ground, and after he couldn’t remember which knee was bothering him during an exam, the Sox traded Manny to the Los Angeles Dodgers.
Manny’s act played well in Los Angeles for a while, but after a failed drug test yielded a 50-game suspension and other Manny acts of random bad behavior, even Hollywood got tired of Manny, and the Dodgers traded him to the Chicago White Sox for the remainder of the 2010 season. Manny failed to do much in Chicago either, hitting just one home run in 24 games.
The end finally came for Manny just six games into the 2011 season, when he suddenly announced his retirement after reports revealed he had tested positive for banned substances a second time.
A great hitter with a horrible ending to a career that will likely not see the light of day in Hall of Fame voting.
4. Steve Carlton: 1965-1988
Steve Carlton is undoubtedly one of the greatest pitchers in the history of baseball, and is one of the top two left-handers in the game along with Warren Spahn. Carlton won four Cy Young awards, won 20 games six times in his career and led the National League in strikeouts five times.
However, from 1985-1988, Carlton was 16-37 with an ERA of 5.21, almost two full runs higher than his career ERA of 3.22. Carlton actually tried to play in 1989 as well, but found no takers.
Carlton believed that his strenuous martial arts training regimen was the key to his longevity in the game of baseball. Too bad it didn’t help his arm any in those final four years.
3. Willie Mays: 1951-1973
Watching the great Willie Mays play was a joy to behold. A natural five-tool player, Mays constantly thrilled with his bat, glove and speed, most notably in the mid-1950s to mid-1960s. Mays continued playing at a high level up until the 1970 season, hitting 28 home runs and registering a .291 batting average.
However, Mays’ skills started to decline in 1971, and in 1972, the San Francisco Giants traded the 41-year-old Mays to the New York Mets for Charlie Williams and $50,000 cash.
Mays’ inglorious ending to his career was marked when he was benched in favor of Don Hahn in center field for the Mets. Mays at the end could barely run, his days as a Met were tarnished by his rapidly diminishing skills. Mays clearly should have retired as a Giant at the end of the 1971 season.
2. Babe Ruth: 1914-1935
In 1934, a 39-year-old Babe Ruth hit 22 home runs with a .288 average for the New York Yankees. But Ruth knew his skills were fast on the decline, and so did the Yankees. Ruth had wanted to manage the Yankees, but Joe McCarthy was firmly entrenched as their skipper and wasn’t going anywhere.
The Yankees traded Ruth to the Boston Braves in February 1935, where Ruth, who was clearly overweight and out of shape, hit just six home runs while batting just .181 in 28 games. Ruth’s skills had deteriorated so much that Braves’ pitchers threatened not to pitch if Ruth was on the field.
Ruth finally called it quits in late May, 1935, and the Braves, who thought Ruth would inject enthusiasm into their team, finished the season 38-115, the fourth-worst record in Major League history.
1. Mickey Mantle: 1951-1968
When Mickey Mantle first appeared in pinstripes with the New York Yankees, he was a can’t miss five-tool player who hit prodigious home run shots and through his tremendous speed was called the “fastest man to first base.”
However, injuries forever played a part during Mantle’s entire career, starting with his rookie season. In the 1951 World Series against the New York Giants, Mantle went after a fly ball hit by fellow rookie Willie Mays.
Playing right field at the time, Mantle stopped when center fielder Joe DiMaggio also converged on the ball and called Mantle off. When Mantle stopped, his cleats caught on a drainage ditch, violently twisting his knee and causing him to miss the rest of the World Series.
While Mantle continued on to greatness, his knees continually got worse over the course of his career. His last good year, 1964, Mantle hit 35 homers with 111 RBI and hit .303. However, the next four years were indeed painful to watch, as the vision of seeing Mantle limping around the bases was a regular sight. After hitting just .245 and .237 in his last two seasons, Mantle finally called it quits in March, 1969.
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