The greatest athletes who never won a championship
Carlos Avila Gonzalez/San Francisco Chronicle via Getty Images

The greatest athletes who never won a championship

There are only so many championships to go around, and unfortunately for some all-time greats, they all did not get a chance to claim one for themselves. From the Stanley Cup to the Larry O’Brien Trophy, to World Cup titles and Olympic Gold, every corner of the sports world has those that have amazing careers but don’t emerge with a championship to their credit. Here is a look at some of the peak performers of all-time that never finished a season as the last man or woman standing.

 
Jeff Bagwell and Craig Biggio
Photo by Brian Bahr/Getty Images

It’s impossible to separate the pair of Astros infielders, who were the backbone of the “Killer B’s” for 15 seasons together in Houston. They were elected to nine All-Star Games (including three together), won five Gold Gloves and Bagwell was named 1994 MVP. Meanwhile, Biggio would join the 3,000 hit club in 2007 and became the first player to be inducted into the Hall of Fame as an Astro….before Bagwell became the second. In 2005, they helped Houston to the franchise’s first World Series appearance but were swept by the White Sox.

 
2 of 60

Ernie Banks

Ernie Banks
Bettmann / Contributor

Few men played baseball with more joy than The Say Hey Kid, who hit 512 home runs and won two MVPs during his nearly two decades with the Chicago Cubs. However, Banks is arguably the greatest player who never made a postseason appearance as well, as the Cubs didn’t post their first winning record of Banks's career until his 11 th season and never finished higher than second place.

 
3 of 60

Charles Barkley

Charles Barkley
Photo by Mitchell Leff/Getty Images

Although he was an 11-time All-Star and All-NBA performer, Barkley never reached the summit of the NBA in his 16-year career. His most successful season came in 1993 –a year where he won league MVP— when he took the Phoenix Suns to the NBA Finals, but ultimately fell in six games to the Chicago Bulls. Barkley was however the leading scorer on two Gold Medal-winning Olympic teams in 1992 and 1996.

 
4 of 60

Elgin Baylor

Elgin Baylor
Bettmann / Contributor

One of the most dynamic and inventive forwards of all time, Baylor’s game was ahead of its time. The 11-time All-Star averaged 27.4 points and 13.5 rebounds for his career and reached the NBA Finals on seven different occasions with the Minneapolis and Los Angeles Lakers. However, he came up short in each one, six times to the Boston Celtics and seventh to the New York Knicks. Sadly, the Lakers would finally win the championship in 1972, but Baylor retired just nine games into the season.

 
5 of 60

Barry Bonds

Barry Bonds
Photo by Kirby Lee/Getty Images

Over the course of his 22-year career, among his many accomplishments, Bonds set records for the most home runs in a career (762) and in a single season (73). He also is the only player to hit 500 home runs and steal 500 bases. No other player has even reached 400 of both stats. After struggling early in his playoff career with the Pittsburgh Pirates, Bonds made the most of his lone World Series appearance in 2002 with the San Francisco Giants. He hit .471 (8-for-30) with four home runs and two doubles while taking 13 walks. However, the Giants fell in seven games to the Anaheim Angels.

 
6 of 60

Pavel Bure

Pavel Bure
Kellie Landis / Getty

One of the most exciting, dynamic goal scorers in NHL history, Bure was a blur shooting across the ice. The “Russian Rocket” averaged more than a point per game over his 12-year NHL career, twice winning the Rocket Richard Award as a top goal-scorer, scoring 60 goals in both 1993 and ’94. In the latter year, he led the NHL in playoff goals with 16, including a memorable double-overtime winner in versus the Calgary Flames in round one. The Canucks would reach the Stanley Cup Finals, but fall to the New York Rangers.

 
7 of 60

Dıck Butkus

Dıck Butkus
Bettmann/Contributor

The innovator of what the middle linebacker position would come to be known for, Butkus was the most feared defensive force of his day. Over the course of his nine-year career with the Chicago Bears, Butkus was an eight-time Pro Bowler and 27 fumbles in his career, while causing an innumerable amount more. But despite his personal dominance, the Bears never had a winning record again after his rookie season before Butkus was forced into early retirement in 1973.

 
8 of 60

Rod Carew

Rod Carew
Hannah Foslien/Getty Images

Carew totaled 3,053 hits lifetime, while seven batting titles and the 1977 American League MVP, a season where he hit .388 for the Minnesota Twins. But over his 19-year career, Carew made only four postseason appearances between the Twins and Anaheim Angels and hit just .221. Aside from a stellar 1979 ALCS, his lifetime postseason average was just .121 (4-for-33).

 
9 of 60

Tina Charles

Tina Charles
Tim Clayton/Corbis via Getty Images

Over the course of her 11-year career, Charles has accomplished a great deal in the WNBA, including picking up Rookie of the Year honors, MVP, and getting seven All-Star nods. However, picking up a title has continued to elude her. Charles has twice reached the conference championship round, once with the Connecticut Sun in 2012, then with the New York Liberty in 2015. Charles joined the Washington Mystics ahead of the 2020-21 season, so perhaps her third stop will be the charm.

 
10 of 60

Ty Cobb

Ty Cobb
Tim Clayton/Corbis via Getty Images

Cobb was undeniably the greatest player of the Deadball Era, setting 90 different records in his career, winning 12 batting titles and twice hitting over .400. The Detroit Tigers star’s .366 lifetime batting average is still the highest of all-time and his record of 4,189 hits stood for 57 years. But despite his individual accolades, Cobb lost in all three of his World Series appearances and saw his lifetime batting average drop over 100 points in postseason play to .262.

 
11 of 60

Marcel Dionne

Marcel Dionne
Bruce Bennett Studios via Getty Images Studios/Getty Images

Dionne was one of the great goal scorers of all time during his 18-year career, mostly with the Los Angeles Kings. He scored 50 goals in six different seasons and 1,771 points, the sixth-best all-time. The “Little Beaver” never advanced past the second round and currently has the most career points all-time for any player who didn’t raise the Stanley Cup.

 
12 of 60

Aaron Donald

Aaron Donald
Mark J. Rebilas-USA TODAY Sports

In short order, Donald has become an all-time caliber defensive line for the Los Angeles Rams. At age 30, he is already a three-time Defensive Player of the Year with 85.5 sacks and 131 tackles for a loss. Donald and the Rams reached Super Bowl LIII but fell to the New England Patriots 13-3.

 
13 of 60

Patrick Ewing

Patrick Ewing
Photo by Focus on Sport/Getty Images

Few –if any— players entered the league with higher expectations than Ewing, the Georgetown superstar who was the centerpiece of the New York Knicks throughout the 1980s and 90s. In his career, he was an 11-time All-Star and three-time All-Defense selection, but along the way, he took some crushing playoff losses at the hands of the Michael Jordan-led Bulls and Reggie Miller’s Indiana Pacers. Ewing helped to lead the Knicks to two Finals appearances, but lost in seven games in 1994 then missed the 1999 Finals with a knee injury.

 
14 of 60

Mike Gartner

Mike Gartner
Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images

This is a distinction that the Hall of Fame defenseman nearly avoided. He was a member of the eventual champion New York Rangers in 1994 but was moved to the Toronto Maple Leafs at the trade deadline. Ironically, the Maple Leaf’s playoff run that same season was the longest of a career that saw him make the playoffs in 15 of his 19 seasons.

 
15 of 60

Ken Griffey Jr

Ken Griffey Jr
Otto Greule Jr/Getty Images

Arguably the most popular player of the last half-century, Griffey’s all-around brilliance in centerfield made him the most exciting player in the sport. His rise brought the Seattle Mariners to new levels of success, including their first postseason appearance in 1995, and his mad dash to score the winning run of the 1995 ALDS against the New York Yankees is the greatest highlight of his career. It also became the only postseason series he would win at age 25.

 
16 of 60

George Gervin

George Gervin
Patrick Gorski/Icon Sportswire via Getty Images

The Iceman was one of the most prolific scorers in NBA history, leading the league in scoring in four different seasons. He made 12 consecutive All-Star appearances between the ABA and NBA and was the all-time leader in nearly every scoring category for the San Antonio Spurs at the time of his retirement. However, although he averaged 28.7 points per game over three Conference Finals appearances, he never advanced to a Championship series.

 
17 of 60

Tony Gonzalez

Tony Gonzalez
Sporting News via Getty Images via Getty Images

Gonzalez was ahead of his time as a weapon at tight end, finishing his career as the all-time leader in catches and receiving yards by a tight end. His 1,325 catches rank third in NFL history and he was a Pro Bowler in 14 of his 17 seasons between the Kansas City Chiefs and Atlanta Falcons. Gonzalez only won a single playoff game in his career, coming in his next to last year in 2012.

 
18 of 60

Tony Gwynn

Tony Gwynn
Focus on Sport/Getty Images

Few in history knew how to handle a bat better than Gwynn, who was an eight-time batting champion and 15-time All-Star. He came the closest to hitting .400 of any player since 1930 when he hit .394 during the strike-shortened 1994 season. Gwynn twice reached the World Series, first in 1984, then again in 1998. However, his Padres teams never fared well, with Gwynn losing eight of his nine career World Series games, although he did hit .500 (8-for-16) versus the Yankees in ’98.

 
19 of 60

Roy Halladay

Roy Halladay
Photo by Jim McIsaac/Getty Images

Halladay spent the first 12 years of his often being the lone star in the sky for the Toronto Blue Jays, who peaked with an 87-win season in 2006. But the two-time Cy Young Award winner wasted no time in making a postseason impact when he finally did reach October with the Philadelphia Phillies, throwing a no-hitter in his playoff debut in 2010 before the Phillies lost in the NLCS. It was the deepest postseason run of Halladay’s Hall of Fame career.

 
20 of 60

Denny Hamlin

Denny Hamlin
Chris Graythen/Getty Images

With 44 career wins, including three Daytona 500 titles, Hamlin’s career has been anything but undecorated. However, after 16 seasons, he is the most accomplished driver ever to not win a Cup Series championship. Part of this is due to the overlap of his career with that of seven-time champion Jimmie Johnson, whom he lost hold of the title to in the season’s final race in 2010 after spinning out during the Ford 400.

 
21 of 60

James Harden

James Harden
Daniel Dunn-USA TODAY Sports

An All-Star in 9 of his 11 seasons to date, a three-time scoring champion, and 2018 MVP, Harden has been one of the most accomplished stars of his era. However, he has been unable to capture his first championship, despite reaching the NBA Finals in 2012 with the Oklahoma City Thunder and reaching the Western Conference Finals on three different occasions with the Houston Rockets.

 
22 of 60

Dale Hawerchuk

Dale Hawerchuk
Bruce Bennett Studios via Getty Images Studios/Getty Images

Hawerchuk was a regular in the playoffs, making appearances in 15 of his 16 career seasons. However, he was stuck with one of the toughest positions to be in historically, as his Winnipeg Jets teams often ran up against the powerhouse Edmonton Oilers of the 1980s. He finally reached the Cup Finals in his last season but was defeated by the Detroit Red Wings. Overall, Hawerchuk saw his season end at the hands of the future Stanley Cup Champions seven times.

 
23 of 60

Jarome Iginla

Jarome Iginla
John Russell/NHLI via Getty Images

The Calgary Flames legend had a decorated career that saw him score 1,300 points, twice with the Rocket Richard Award, the Art Ross Trophy, and receives the Pearson Award as MVP voted by the players in 2002. In 2020, Iginla was elected to the Hockey Hall of Fame, but he will enter the Hall without a Stanley Cup to his credit. The closest he came was in 2004 when the Flames barely fell to the Tampa Bay Lightning.

 
24 of 60

Allen Iverson

Allen Iverson
Ezra Shaw/Getty Images

Basketball’s most prolific small scoring guard, Iverson was one of the most influential players of all time both on and off the court. His 2001 season was one of the greatest singular effort campaigns in NBA history, as he won MVP after averaging 31 points per game and leading the Philadelphia 76ers to the NBA Finals. In Game 1 of the series, he scored 48 points and gave the Los Angeles Lakers their first –and only— playoff loss on the year, as the Sixers would fall four games to one in Iverson’s only Finals appearance.

 
25 of 60

Harry Kane

Harry Kane
Tim Groothuis-Witters Sport-USA TODAY Sports

The Tottenham star has become one of the best strikers in the world and could have a massive sum offered up for his services this summer. However, he has yet to turn in a significant title in his career. He did reach the 2019 UEFA Champions League final but fell to Liverpool. Kane is in the middle of his prime and has the chance to make a critical decision about how to add some hardware to his trophy case in the near future.

 
26 of 60

Jim Kelly

Jim Kelly
Owen C. Shaw/Getty Images

No athlete’s legacy is more defined by not winning the big one than Kelly’s, who led the Buffalo Bills to four consecutive Super Bowl losses between 1990 and 1993. A five-time Pro Bowler and Hall of Famer, the Bills reached the playoffs in eight of his 11 seasons at the helm. However, on Super Sunday, Kelly struggled mightily tone of two touchdowns versus seven interceptions over his four appearances and was knocked out of Super Bowl XXVII in the second quarter.

 
27 of 60

Michelle Kwan

Michelle Kwan
Stuart Franklin/Getty Images

A nine-time U.S. Champion and five-time World Champ, Kwan is one of the most decorated and successful figure skaters of all time. However, she also is one of the most notable performers that never claimed an Olympic gold as well. She claimed the Silver in 1998 but then moved back to claim Bronze in 2002. A groin injury and subsequent knee surgery had her opt-out of the 2006 Games and unfortunately secured her place as arguably the greatest skater of all-time to never claim a Gold Medal in an otherwise amazing career.

 
28 of 60

Nap Lajoie

Nap Lajoie
GHI/Universal History Archive via Getty Images

A Triple Crown winner in 1901 when he hit .426 for the Philadelphia A’s, it was the first of five batting titles for Lajoie, who was a member of the inaugural Baseball Hall of Fame class. However, team success was something that rarely followed Lajoie, as a second-place finish by the 1908 Cleveland Naps (named for him) was the best of his career. Lajoie never played in a World Series game across his 21-year career.

 
29 of 60

Dıck "Night Train" Lane

Dıck "Night Train" Lane
Bettmann / Contributor

One of the premier cornerbacks of all-time, Lane twice led the NFL in interceptions in a season, totaling 68 in his career, the fourth-most of all-time. His 14 picks as a rookie in 1952 remain the single-season record and he was an even more vicious tackler he was strong in coverage. However, he spent the majority of his career with the Chicago (now Arizona) Cardinals and Detroit Lions, who remain among the Super Bowl-less franchises in league history, thus he never claimed a title.

 
30 of 60

Eric Lindros

Eric Lindros
Bruce Bennett Studios via Getty Images Studios/Getty Images

Concussion and controversy kept Lindros ever realizing his full potential, but he did win both the Hart Trophy and Lester B. Pearson Award as MVP in 1995. Two years later, Lindros made his only Finals appearance, which resulted in a sweep at the hands of the Detroit Red Wings, after the Flyers had dropped just one game in each of the previous three rounds. Lindros was responsible for 26 points in 19 games during the run.

 
31 of 60

Karl Malone

Karl Malone
GEORGE FREY/AFP via Getty Images

An 11-time All-Star, The Mailman’s 36,928 points are the second-most in NBA history, behind only Kareem Abdul-Jabbar. He made two consecutive NBA Finals appearances in 1997 and ’98 with the Utah Jazz, the first of which came on the heels of being named league MVP. However, in both instances, he fell to Michael Jordan and the Chicago Bulls in six games. In his final season in 2004, he joined the Lakers in his final attempt at a title but was upset by the Detroit Pistons.

 
32 of 60

Dan Marino

Dan Marino
RHONA WISE/AFP via Getty Images

Marino did nearly everything possible in football besides winning a Super Bowl, which sealed his fate as arguably the best player in history to win a championship. A nine-time Pro Bowler and 1984 MVP, Marino led the NFL passing yards five times and touchdowns on three occasions, in route to becoming the NFL’s all-time passing leader upon his retirement with 61,361 yards. Marino threw for 318 yards in Super Bowl XIX but lost to the San Francisco 49ers 38-16.

 
33 of 60

Bruce Matthews

Bruce Matthews
George Gojkovich/Getty Images

One of the most versatile and dominant offensive linemen of all time, Matthews was selected to 14 Pro Bowls over his 19-year career, all spent with the Houston Oilers/Tennessee Titans franchise. His 293 games started are third-most in NFL history and he never missed a game to injury. Matthews made his lone sole Super Bowl appearance in 1999 when the Titans came within a yard of defeating the St. Louis Rams.

 
34 of 60

Angel McCoughtry

Angel McCoughtry
Julio Aguilar/Getty Images

McCoughtry’s resume is a brilliant one, as the top pick in the 2009 WNBA Draft certainly has delivered on the promise. In 10 seasons with the Atlanta Dream, she twice led the league in scoring and topped 20 points per game five times. McCoughtry has also been a two-time All-WNBA First Team pick and seven-time All-Defense member. But despite reaching the Finals four times, three with the Dream and once with the Las Vegas Aces last summer, but is still yet to add that final piece to her Hall of Fame resume.

 
35 of 60

Tracy McGrady

Tracy McGrady
Ronald Martinez/Getty Images

A seven-time All-Star and two-time scoring champion who once scored 13 points in 35 seconds, McGrady was one of the most exciting and skilled scorers of his era. Yet during the prime of his career as a headline superstar, he never was able to advance beyond the first round of the playoffs. This came despite the fact he averaged 29.8 points per game over five consecutive seasons Round 1 exits with both the Orlando Magic and Houston Rockets.

 
36 of 60

Reggie Miller

Reggie Miller
Sporting News via Getty Images via Getty Images

One of the most fearless shooters in the NBA history, much of the legend of Reggie Miller stemmed from his heated showdowns with the New York Knicks and Chicago Bulls in the 1990s. Despite some legendary performances, Miller never advanced to the NBA Finals until 2000, when the Indiana Pacers faced the Los Angeles Lakers. Although Miller averaged 24 points per game in the series, the Pacers fell in six games in the only Finals appearance of his 18-year career.

 
37 of 60

Randy Moss

Randy Moss
Rob Tringali/Sportschrome/Getty Images

The most athletically gifted wide receiver in NFL history, Moss changed the way the game was played with his size and speed. He made an immediate impact as a rookie in 1998, helping the Minnesota Vikings to a 15-1 record and to the brink of reaching the Super Bowl, if not for a missed kick by Gary Anderson. In 2007 with the New England Patriots, Moss finally reached his first Super Bowl and scored a touchdown as the Patriots were looking to close out an undefeated season. However, a miraculous fourth-quarter performance by Eli Manning snatched Moss’ best chance at a championship from him.

 
38 of 60

Anthony Munoz

Anthony Munoz
Peter Brouillet/Getty Images

Considered by many to be the greatest offensive tackle of all time, Munoz’s arrival in Cincinnati ushered in the greatest era of success in the franchise’s history. Munoz made 11 Pro Bowls in his 13-year career and helped the Bengals to four playoff appearances and two Super Bowls, both of which came as losses to the San Francisco 49ers. In both Super Bowl XVI and XXIII, the Bengals’ defeats came by less than a touchdown’s difference.

 
39 of 60

Steve Nash

Steve Nash
Christian Petersen/Getty Images

It could be argued that Nash is the most accomplished NBA player of all-time to never reach the Championship round. He led the NBA in assists five times at the helm of the high-powered Phoenix Suns of the early 2000s, capturing back-to-back MVP honors in 2005 and 2006. However, Nash never broke through to the NBA Finals and as it currently stands, he is the only multi-time MVP in NBA history to never win a title in his career.

 
40 of 60

Cam Neely

Cam Neely
Jessica Rinaldi/The Boston Globe via Getty Images

A true warrior that often fought through injuries to put his prodigious talent on display, Neely put 50 pucks in the net in back-to-back seasons in 1990 and ’91. Between 1988 and 1991, Neely scored 74 points over 73 playoff games, a run where the Bruins twice lost in the Stanley Cup Finals to the Edmonton Oilers and lost in the Conference Finals to the Pittsburgh Penguins as well. Neely was limited to just nine playoff games over the final five seasons of his career due to knee injuries.

 
41 of 60

Adam Oates

Adam Oates
Mitchell Layton/Getty Images

No player has been more productive in the Stanley Cup Playoffs to never raise the title than Oates was. He is 27th all-time in postseason scoring with 48 points and twice reached the Finals, with the Capitals in 1998, then again with the Mighty Ducks of Anaheim in 2003. He experienced both extremes of playoff pain, being swept at the hands of the Red Wings, before falling in seven games to Devils as a 40-year-old.

 
42 of 60

Brad Park

Brad Park
Bruce Bennett Studios via Getty Images Studios/Getty Images

Perhaps no player in hockey history had a more pronounced habit of coming up just outside the winner’s circle. Although Park made the playoffs in every season of his NHL career, he never won the Stanley Cup. This came despite three trips to the championship round, including losing to the Bruins with the Rangers in 1972, then losing in consecutive years losing as a member of the Bruins in 1977 and ’78. Add in his six runner-up nods for the Norris Trophy and your heart has to go out to him.

 
43 of 60

Chris Paul

Chris Paul
Robert Hanashiro-USA TODAY Sports

Paul’s latest attempt was his greatest attempt. At age 36, CP3 broke through to the NBA Finals for the first time, but fell in six games to the Milwaukee Bucks, ending a heroic run for the Phoenix Suns, who were also seeking their first title in franchise history. It is the latest of heartbreaking attempts to reach the summit of the NBA, as he enters the twilight of a career that has seen him reach the playoffs in 14 of 15 campaigns, leading five different teams to the postseason in the process.

 
44 of 60

Gilbert Perreault

Gilbert Perreault
Bruce Bennett Studios via Getty Images Studios/Getty Images

After being the first overall pick in the 1970 Draft by the Buffalo Sabres, Perreault would go on to spend his entire 17-year career with the team, scoring 1,326 points in the process. The longest playoff run of his career came in 1975 when the Sabres faced off against the defending champion Philadelphia Flyers in the Cup Finals. Perreault’s famous French Connection line was famously stopped late in Game 6 by Flyers goalie Bernie Parent in a momentum-swinging moment that swung the fate of his best shot at raising the Cup.

 
Cristiano Ronaldo
Dean Mouhtaropoulos/Getty Images

Without a doubt, Ronaldo is one of, if not the, most famous and decorated footballers of all time. While he is a five-time Ballon d’Or winner, with five Champions League titles and one EURO title as well. With this legacy of achievements, it could be argued that the Portuguese legend doesn’t deserve placement on this list at all. However, a career-capping World Cup victory remains outside of his grasp, with his best showing being a third-place showing back in 2006. At age 36, he may have one more run left him to scratch this final missing title of note from his record in 2022.

 
46 of 60

Barry Sanders

Barry Sanders
Damian Strohmeyer/Allsport/Getty Images

During his decade with the Detroit Lions, Sanders entrenched himself as one of the most dynamic, exciting runners in NFL history. He averaged 1,500 yards per season and topped 2,000 yards in 1997, before retiring suddenly in 1998 at age 30 with 15,269 yards, the second-most in NFL history. Despite his brilliance, Sanders claimed his only playoff win in his third season, as Detroit exited in the Wild Card round on four other occasions.

 
47 of 60

O.J. Simpson

O.J. Simpson
Ross Lewis/Getty Images

The Juice was the NFL’s leading rusher for the decade in the 1970s, leading the league in yards four times, including becoming the first 2,000-yard rusher – and the only player to do it with a 14-game schedule. Despite this, the Bills only made the playoffs once with Simpson in 1974, who was limited to 49 yards against the vaunted Steel Curtain defense of the Pittsburgh Steelers.

 
48 of 60

Bruce Smith

Bruce Smith
Focus on Sport/Getty Images

Another Buffalo Bills great who never got across the finish line in the early 90s, Smith was one of the greatest defensive linemen of all time. Smith was an 11-time Pro Bowler and two-time Defensive Player of the Year, finishing his career with 200 sacks, the most in NFL history. Smith totaled two sacks across his four Super Bowl appearances.

 
49 of 60

John Stockton

John Stockton
Matt A. Brown/Icon Sportswire via Getty Images

The NBA’s all-time leader in both assists and steals, Stockton spent his entire 19-year career with the Utah Jazz, remarkably making the playoffs every year of his career. He formed one of the most famous duos in NBA history alongside Karl Malone, with whom he spent 18 of those years. The Jazz reached the NBA Finals in 1997 and 1998, but lost on both occasions, with Stockton averaging 12 points and eight assists over 12 Finals games.

 
50 of 60

Peter Statsny

Peter Statsny
Bruce Bennett Studios via Getty Images Studios/Getty Images

Stastny was a points machine in the early going of his career with the Quebec Nordiques, topping 100 points in seven of his first eight seasons. However, they were never able to get past the Wales Conference Finals, being swept by the New York Islanders in 1982, then falling in six games to the Philadelphia Flyers three years later. After being dealt to the New Jersey Devils during the 1990 season, he never made it past the divisional round.

 
51 of 60

Mats Sundin

Mats Sundin
Graig Abel/Getty Images

Sundin reached the playoffs in 10 of his 13 seasons with the Toronto Maple Leafs but was unable to break their long-standing Cup drought in the process. He reached the conference finals three times in 1994, 1999 and 2002, but never got over the hump. Had he been able to stay with his original club, the Quebec Nordiques –the future Colorado Avalanche— Sundin would’ve picked up two Cups in his career.

 
52 of 60

Derrick Thomas

Derrick Thomas
DAVE KAUP/AFP via Getty Images

Nearly as soon as Thomas arrived in Kansas City in 1989, the Chiefs took off. Between 1990 and 1997, they never finished lower than 2nd place in the AFC West. Meanwhile, Thomas became the most fearsome linebacker in the NFL, with Thomas being named an All-Pro each season. However, a string of crushing playoff disappointments saw Thomas reach as far as the AFC Championship Game just once before his tragic car accident and subsequent death in 1999 at age 33.

 
53 of 60

Joe Thornton

Joe Thornton
Dan Hamilton-USA TODAY Sports

Time is getting short for Thornton’s long-time pursuit of the Stanley Cup. The first overall pick in the 1997 NHL Draft won only one playoff series in seven seasons with the Boston Bruins, who would go on to win the Cup a few years after dealing him away to San Jose. With the Sharks, Thornton reached the playoffs in 12 of 14 seasons, but lost in six games to the Pittsburgh Penguins in the Cup Finals in 2016, while falling in the conference finals three other times.

 
LaDainian Tomlinson
Robert B. Stanton/NFLPhotoLibrary

One of the greatest all-purpose threats of all-time out the backfield, Tomlinson was one of the busiest and best running backs of his generation. During his nine years with the San Diego Chargers, the team won the AFC West title five times, with Tomlinson winning MVP in 2006 when he scored 31 total touchdowns. However, San Diego only reached as far as the AFC Championship Game once and lost in the Wildcard round on three other occasions.

 
55 of 60

Mike Trout

Mike Trout
Joe Nicholson-USA TODAY Sports

While Trout is still in the process of crafting his legacy, his accomplishments to date deem him worthy of looking at how regularly early his seasons have ended. When Trout turns 30 in August 2021, he will have won three AL MVPs and have played at an astonishing level of producing nearly 30 more Wins Above Replacement level than his closest competition since 2012. Despite that, Trout has appeared in only three postseason games thus far, in 2014 when he went 1-for-12 (the sole hit being a home run) over a three-game sweep at the hands of the Kansas City Royals.

 
56 of 60

Pierre Turgeon

Pierre Turgeon
Elsa Hasch /Allsport

One of the more underrated players of all-time, Turgeon made an early impact with the Buffalo Sabres, before later winning the Lady Byng Trophy with the New York Islanders in 1993. However, he played his most significant playoff hockey as a member of the St. Louis Blues between 1997 and 2001, when he had the terrible luck of being beaten by the future Stanley Cup Champions in four of his five seasons with the Blues, which included capturing the Presidents’ Trophy in 2000, before being upset in the first round by the #8 seeded San Jose Sharks.

 
Russell Westbrook
Bill Streicher-USA TODAY Sports

A nine-time All-Star, two-time scoring champ, and all-time leader in triple-doubles with 184 (and counting), Westbrook has accomplished some extraordinary feats in his career. Alongside Kevin Durant and James Harden, Westbrook reached the NBA Finals in his fourth season, falling to the Miami Heat in five games. Since then, he has reached the Conference Finals once in 2016 but has also made Round 1 exits in five of the last season seasons.

 
58 of 60

Dominique Wilkins

Dominique Wilkins
Focus on Sport via Getty Images

One of the most exciting players of all time, Wilkins was as much a victim of bad timing in his career, as any particular failure of his own. His career ran parallel against those of Larry Bird, Michael Jordan, and Isiah Thomas, whose teams ended seven of the 10 playoff runs for Wilkins. Still, a nine-time All-Star and 1986 scoring champ who averaged 24.8 points for his career, his legendary Game 7 shootout versus Bird in 1988 saw Wilkins erupt for 48 points, but see the Hawks lose 118-116.

 
59 of 60

Ted Williams

Ted Williams
Bettmann/Contributor

A lifetime .344 hitter who made 19 All-Star appearances and hit 521 home runs, The Splendid Splinter is on the shortlist for the greatest hitter of all time. However, his Boston Red Sox tenure coincided with a stretch of the New York Yankees reaching the World Series 14 times, as well as him twice leaving for active duty during World War II and the Korean War. His lone World Series appearance came in 1946 when he hit just .200 after being hit in the elbow with a pitch just before the Series started. The Red Sox would lose to the St. Louis Cardinals in seven games.

 
60 of 60

Carl Yastrzemski

Carl Yastrzemski
Bettmann/Contributor

Yaz played 23 years at Fenway Park and became the club’s all-time leader in hits, RBI, total bases, and games played, among other accomplishments. An 18-time All-Star, three-time batting champ, and 1967 MVP when he completed the AL Triple Crown, Yastrzemski twice led the Red Sox to the World Series, and although he came away without a victory, it certainly wasn’t his fault. Over 17 postseason games, he hit .369 with four home runs and a .447 on-base percentage.

Matt Whitener is St. Louis-based writer, radio host and 12-6 curveball enthusiast. He has been covering Major League Baseball since 2010, and dabbles in WWE, NBA and other odd jobs as well. Follow Matt on Twitter at @CheapSeatFan.

More must-reads:

Customize Your Newsletter

+

Get the latest news and rumors, customized to your favorite sports and teams. Emailed daily. Always free!

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.