The number of legendary players that have retired from professional sports in the past six years is staggering. The NHL lost Teemu Selanne and Martin St. Louis, the NBA lost Kobe Bryant and Tim Duncan, and Peyton Manning and Randy Moss bid farewell to the NFL. Major League Baseball has also had its fair share of elder statesmen call it quits since 2011. Unfortunately for New York Yankees fans, many of the players who have recently hung up their cleats wore the pinstripes during the Yankees dynasty of the late-1990s and early-2000s.
A number of these former stars were involved in the steroid scandals that plagued baseball in the late-'90s and early-2000s, harming their reputations and possibly damaging their chances of getting voted in MLB’s Hall of Fame. A handful of perennial All-Stars and future Hall of Famers also make up this list, including two-time World Series champ David Ross, who ended his career as all athletes wish they could, going out on top, as a member of the Chicago Cubs squad that broke their 108-year streak of futility. Ross and fourteen other players who now call themselves former MLB stars can be found below, along with an explanation of where they find themselves in their post-playing days.
16 Andy Pettitte
Pettitte is the first of five prominent New York Yankees players on this list. The southpaw pitcher from Baton Rouge, Louisiana began his career at Deer Park High School in Texas, before being drafted by the Yankees after his senior year. He opted to spend one year at San Jacinto Junior College before signing his first pro contract with the Bronx Bombers.
After four seasons in the minors, where Pettitte met his future teammates Jorge Posada and Derek Jeter, the lefty finally made his Yankees debut in 1995. Over the next 18 seasons, Pettitte became one of the busiest and winningest pitchers of his time. Except for a brief three-season stint with the Houston Astros, the pitcher spent his career in pinstripes as a member of the Yankees. Upon his return to the Yankees for the 2007 season, Pettitte admitted to using PEDs to heal from an elbow injury in 2002, unfortunately damaging his chances of getting into the Hall of Fame in the future. He announced his first retirement following the 2010 season, but this only lasted for one year. Pettitte couldn’t quell the competitive fire inside of him and returned for two more seasons before calling it quits for real in 2013. The southpaw finished his illustrious career with five World Series rings to compliment his record-setting 19 career postseason wins in another record-setting 42 career postseason starts.
Pettitte has taken things easy since his retirement. He occasionally appears at Yankee Stadium for ceremonies honouring his former teammates, and had his own number 46 retired by the Yanks in 2015. Mostly, though, the Louisianan has spent his days with his family. He has helped to coach his two youngest sons’ football teams, while watching his eldest, Josh, pitch at Rice University, after he followed in his dad’s footsteps as a New York Yankees draftee. Pettitte lends his expertise as an assistant coach to former teammate, and co-member of this list, Lance Berkman, at Second Baptist, a Texas high school.
15 Kevin Youkilis
Youkilis, also known as “Youk”, played in MLB for 14 years, establishing himself as one of the most reliable, consistent catchers in the game.
Youkilis attended Sycamore High School in Cincinnati, where he played four different positions, which led to him winning the Amateur Athletic Union National Championship in 1994. In 1997, he graduated and had two schools attempting to recruit him for Division I ball, but of the two, he chose the University of Cincinnati, staying in his hometown. In the 2001 MLB draft, Youkilis was drafted by the Boston Red Sox in the 8th round. For the following three years he played with the Red Sox’s farm teams until he was called up as a third-baseman in 2004.
For the next eight years, Youkilis played for the BoSox, winning many different awards for his performances on the field. Then, in 2012 he was traded to the Chicago White Sox, and again to the Yankees one year later. His catching career began to take its toll on his body here as he suffered a back strain, being placed on a 15-day DL. Upon returning, he re-injured his back, needing surgery just days later. His physical abilities diminished, Youkilis played his final season of professional baseball in Japan before announcing his retirement in 2014. He finished his career with two World Series rings and three MLB All-Star nods on his resumé.
Since Youkilis’ retirement, he has still been prevalent in the baseball world, working with the Chicago Cubs as a scouting and development consultant. Also, in 2016, Youkilis and his brother opened Loma Brewing Company in Los Gatos, California.
14 Ryan Dempster
This Canadian-born MLB starter and reliever played for a variety of teams throughout his 18-year career.
Dempster was drafted by the Texas Rangers in the 1995 MLB draft. In one year with the franchise, he bounced around their minor league clubs before being traded to the Florida Marlins in 1996. Two years later, Dempster made his major league debut with the Marlins and continued to play with them for four years until he was traded to the Cincinnati Reds in 2002. He only spent one year in Cincy before being traded to the Chicago Cubs, where he spent the majority of his career. During this time he emerged as one of the most consistent relievers in baseball and by 2007 he earned a spot in the starting rotation. He was then traded to the Texas Rangers in 2012, and to the Boston Red Sox in 2013, which ended up being his final year in MLB. In 2014, prior to spring training, Dempster called it quits.
Since his retirement, Dempster was hired by MLB Network as a studio color analyst. Later in 2014, it was announced that Dempster would be taking a job with the Cubs’ front office as an assistant to their general manager and president of baseball operations. Dempster has remained in the baseball loop, and even pitched for Team Canada in the 2017 World Baseball Classic at the age of 39.
13 Jason Giambi
Giambi is yet another late-90s baseball player to have his otherwise-successful reputation tarnished due to PED use.
Giambi was a tri-sport athlete at South Hills High School, excelling baseball, football and basketball. He was then selected by the Milwaukee Brewers in the 1989 MLB draft but declined and attended college at Long Beach State University. In the 1992 draft, he was selected by the Oakland Athletics in the second round and, after signing with them, spent three years playing for their farm teams. After breaking into the big leagues, he stuck with the Athletics from 1995-2001. From 2002 until his retirement, he bounced around from the New York Yankees, back to Oakland, then to the Colorado Rockies, and finally to the Cleveland Indians where he retired after the 2014 season. Over the 13 years he played Major League Baseball, Giambi won many awards, including an A.L. MVP nod and five All-Star selections. These accomplishments, however, were overshadowed due to his involvement with the BALCO PED scandal.
Giambi is now one of the co-owners of Hotel Casa Cielo, in Cabo San Lucas, Mexico. He resides in Henderson, Nevada with his wife, where he helps her manage the lingerie and loungewear company that she started.
12 Josh Beckett
Beckett was seen as one of the best prospects of his time and, though he did have an injury-riddled career, he lived up to expectations when it mattered most.
The Spring, Texas native was a standout in high school and bypassed collegiate baseball, jumping straight to the pros after being drafted by the then-Florida Marlins in 1999. After two outstanding seasons in the minors, where he was awarded the organization’s Minor Leaguer of the Year award, Beckett made his MLB debut in 2001. He had five solid but injury-hampered seasons in Florida, leading the team to a World Series title in 2003 and earning World Series MVP honours. He was then traded to the Boston Red Sox, where he won another World Series in 2007, being named the MVP of the ALCS along the way. Past his prime, Beckett spent the final three seasons of his 14-year career as an L.A. Dodger before more injuries forced him to call it a career in 2014. As his postseason accomplishments indicate, Beckett was one of the best clutch pitchers of the 2000s.
Since his retirement, the righty pitcher has stayed quiet and out of public. He spends his days with his wife and two daughters, and his free time on his favourite hobby, deer hunting, on his 7,000-acre ranch in Cotulla, Texas.
11 Todd Helton
Helton is a former MLB first baseman who spent his entire 17-year career with one team, the Colorado Rockies. He is the only person to have his number retired with the club.
The Knoxville, Tennessee native excelled in both baseball and football at Central High School. After his senior year, he was drafted to the San Diego Padres in the 1992 MLB draft but decided to go the college route instead, taking up the University of Tennessee on their scholarship offer. After three solid seasons there, Helton was again selected in the 1995 MLB draft by the Colorado Rockies, 8th overall. He spent two years bouncing around the minor leagues with the Colorado Rockies’ affiliates before making his debut in 1997. After 17 strong seasons, Helton announced his retirement in 2013. He had earned approximately 40 different awards for his success within the sport, including three Gold Gloves, four Silver Sluggers, and five All-Star nods.
Similar to Beckett, Helton has kept quiet since his retirement. His only notable publicity was when was honoured by the Rockies in 2014 as they retired his number 17 jersey. He currently resides in Brighton, Colorado with his wife and their two daughters.
9 Lance Berkman
Berkman, also known as “Big Puma”, is one of the most charitable men to ever play the game of baseball. Not to take away from his tremendous on-field abilities, he is also one of the best switch-hitters to ever play the game.
Berkman began his road to the big leagues at Rice University, where was named the 1997 National College Player of the Year after hitting the third-most long-bombs in NCAA history with 41. The Houston Astros took the big Texan, a native of Waco, in the first round of the 1997 draft and, after playing two and a half years in the minors, he was called up to the big league squad. Despite being on a number of powerhouse Astros clubs, Berkman had to wait until his 2011 signing with the St. Louis Cardinals for his first and only World Series ring. The Big Puma retired after the 2013 season, signing a one-day contract with the team that drafted him so that he could retire as an Astro. Berkman finished his career with the record for the most home runs and RBIs in a single season by a switch-hitter. The outfielder/first-baseman was known for his charitable efforts, running a group called the “Berkman Bunch” which allowed underprivileged kids to meet him before games and donating just over $2.4 million to the “To The Lord’s Fund” charity. He was named to Forbes’ 30 Most Generous Celebrities for his actions.
Since Berkman hung up his cleats, he has lent his expertise to a Houston-area high school, Second Baptist, where he has been the head baseball coach since 2015. He also continues his charitable efforts with the two foundations he runs.
8 Mark Teixeira
Teixeira is a great humanitarian and an even better baseball player. He created one scholarship himself and also gives one out in partnership with his wife.
He began his career playing college baseball at Georgia Tech. Over his career, Teixeira suited up for the Texas Rangers, Atlanta Braves, Los Angeles Angels, and, most memorably, the New York Yankees, but the first baseman was originally drafted by the Rangers 5th overall in 2001. He is viewed as one of the most prolific switch hitters in MLB history and contributed greatly to the Yankees’ 27th World Series championship in 2009. Over his time playing MLB baseball, he was a three-time All-Star, won five Gold Glove Awards, and three Silver Slugger Awards. Teixeira also holds the all-time MLB record for most games with a home run from both sides of the plate with 14. At the end of 2016, Teixeira announced his retirement as a result of wear-and-tear from various injuries throughout his career.
Teixeira set up a scholarship at his high school in honour of a friend that passed away in a car accident. Him and his wife also established the Mark Teixeira Charitable Fund. Since his retirement, the Maryland native has joined ESPN as an analyst.
7 Mariano Rivera
The man affectionately known as “Mo” is undoubtedly the best closer to ever play Major League Baseball and is a lock to be inducted into the Hall of Fame once he is eligible in 2019.
After growing up very under-privileged in a small suburb of Panama City, Panama, Rivera didn’t even play serious organized baseball until he was in his late-teens. He began as a shortstop, but transitioned to pitching at age 19 when his club’s regular pitcher was under-performing. His immediate success led to the New York Yankees scouts inviting him to a tryout and signing him to an international amateur contract in 1990. After five years of seasoning, learning English, and posting incredible numbers, Rivera made his debut with the Pinstripes in 1995. After an up-and-down rookie season as a starter, the club decided to move him to the bullpen, and by 1997, he was the team’s full-time closer. After 17 more lights-out, record-setting seasons, Rivera hung up his cleats in 2013. He finished his career with five World Series rings and THIRTEEN All-Star nods. The clutch righty has a career ERA of 2.21 to go along with his 652 saves, both MLB career records.
“Mo” has had a diverse life since his retirement. He has been bestowed with many awards, including two for his humanitarian efforts in his native Panama, and has been honoured by the Yankees in a number of ceremonies, having his #42 jersey retired in 2014. The future Hall of Famer has invested in and endorsed a wide variety of businesses, including restaurants and a car dealership. The busy man has also been assisting his eldest son, Mariano III, hone his craft as a pitcher. He has been drafted by both the Yankees and the Washington Nationals and currently plays in their minor league system.
6 Chipper Jones
The only other man in this article besides Lance Berkman on the shortlist as the best switch-hitter in MLB history, Jones spent his entire 23-year pro career in the Atlanta Braves organization.
Born Larry Wayne Jones Jr., but known as “Chipper” because he was a “chip off the old block” of his father, who also played and coached baseball, the DeLand, Florida native played his pre-MLB baseball at both Taylor High School and Bolles School. After his senior year, Jones was taken first overall by the Braves in 1990. After three minor-league seasons, Jones made his debut near the end of the 1993 season, but missed the 1994 campaign with a torn ACL, making 1995 his official rookie year. Other than two seasons at left field in 2002 and 2003, the switch-hitter was the starting third baseman for the Braves for seventeen outstanding seasons before announcing his retirement from the sport in 2012. He finished his HOF-worthy career with a World Series title, an NL MVP, and eight All-Star nods to his name.
Jones has stuck around baseball since his retirement. He was honoured by the Braves, having his #10 jersey retired and being inducted into the team’s hall of fame in 2013. He has since signed on as an advisor to the organization, a position he has fulfilled since 2015. An avid hunter, Jones also has two TV shows: Major League Bowhunter, which he runs with friends, and Buck Commander, which he runs with three former teammates and Duck Dynasty star Willie Robertson.
5 Derek Jeter
Jeter is one of, if not THE best and most consistent shortstops to ever play the game. The former Yankee is a surefire MLB Hall of Famer once he becomes eligible for induction in 2020.
Jeter played his high school baseball at Kalamazoo Central, where he won three different High School Player of the Year awards following his senior season. The Houston Astros had the first overall pick in 1992 but passed on Jeter as they thought he would want to go to college rather than signing with them. The next four teams to pick shared that sentiment and the outstanding shortstop fell to the Yankees, 6th overall. Following three and a half minor league seasons, the man who came to be known as “Captain Clutch” made his MLB debut in 1995. He never looked back from there, becoming the team’s starting shortstop in 1996 and leading the Pinstripes for nineteen more incredibly consistent seasons until his retirement in 2014. Jeter finished his Hall of Fame-worthy career with five World Series rings, five Gold Glove and Silver Slugger awards, and 14 All-Star game selections. He is just as well known for his leadership as he is for his playing abilities, also serving as the Yankees’ captain from 2003-2014.
Jeter has remained active since hanging up his cleats, partaking in a number of business ventures such as a publishing company and The Players Tribune website. He also runs his own charity, the Turn 2 Foundation, helping teens avoid drug and alcohol addiction. Jeter and his wife, model Hannah Davis, recently announced that they will be having their first child in mid-2017.
4 Michael Young
Young, a now-40-year-old MLB retiree, was known for his versatility. He spent much of his career as a second baseman, but was also an MLB All-Star five times as a shortstop, once as a third baseman, and once as a DH/utility infielder.
Young began his career playing baseball at Bishop Amat Memorial High School and then attended college at University of California, Santa Barbara. In 1994 he was drafted by the Baltimore Orioles but decided to return to college. Three years later, in the 1997 MLB draft, Young was taken 25th overall by the Toronto Blue Jays. After three minor-league seasons with the Bluebirds, was traded to the Texas Rangers where he made his MLB debut in 2000 and remained for the majority of his career until 2012. In 2013, the California native split the season between the Philadelphia Phillies and L.A. Dodgers before retiring in early 2014. Having his career year in 2003, the versatile Ranger was 3rd in the league in hits with 204, led all second basemen with a batting average of .306, and had a stellar fielding percentage of .987. Showing his versatility and consistency, Young also won the A.L. batting title in 2005 as a shortstop with an average of .331.
Since his retirement, Young has donated money to his alma mater, the University of California, in order to refurbish the school’s baseball field. He has also been running the Michael Young Family Hispanic Scholarship Program with his wife. Young has recently been recognized for his productive career, being inducted into the Texas Rangers’ Hall of Fame in a pregame ceremony in 2016.
3 Alex Rodriguez
A-Rod is one of the most controversial players of the past twenty-five years. He has had a great career on the field, but has also had plenty of issues off of it.
Rodriguez had great numbers as a high school player at Westminster Christian School and, like many of the stars on this list, chose to forego college, signing with the Seattle Mariners who has selected him 1st overall in the 1993 MLB draft. He spent only three months in the minors before being called up to the show at the ripe old age of 18. After seven years in Seattle, A-Rod made a brief two-season pitstop in Texas with the Rangers before landing with the New York Yankees in 2004. He spent the most memorable years of his career in pinstripes before his diminishing abilities forced him to hang up his cleats in 2016. A-Rod has an incredible laundry list of accomplishments, including a World Series title, three A.L. MVP crowns, and 14 All-Star game appearances, but all of this is overshadowed by his negative off-field reputation. In 2013, it was revealed that A-Rod was involved in the Biogenesis PED scandal and he suffered the longest suspension in MLB history: 162 games.
In the eight months since his retirement, Rodriguez has remained in the public’s eye. He worked with Fox Sports as an analyst during the 2016 playoffs and has recently announced a relationship with singer Jennifer Lopez.
2 David Ross
Ross is a recently retired, two-time World Series champ who is most recognized for his recent 2016 win with the Chicago Cubs, breaking their 108-year dry spell.
Ross was born in Bainbridge, Georgia but went to highschool at Florida High School where he played on their baseball team. In 1995, he was drafted by the L.A. Dodgers but chose to attended Auburn University instead of signing with them. In the 1998 draft, the Dodgers selected Ross again, and this time he signed with them. From here, he played two years with the Dodgers before bouncing around with six different teams from 2005-2015, ending up with the Cubs. In Ross’ final season, after having already played 15, he helped the Cubs win the 2016 World Series, becoming the oldest player to hit a home run in World Series history.
Since his retirement last season, Ross has found a new hobby, becoming one of the contestants competing on season 24 of Dancing with the Stars. “Grandpa Rossy” is the first pro baseball player to ever compete on the show.
1 David Ortiz
The Dominican legend, lovingly referred to as “Big Papi”, is one of the most dangerous power hitters of his generation.
Ortiz was a standout at Estudia Espaillat High School in his native Dominican Republic and signed an amateur contract with the Seattle Mariners at the tender age of 17. When he first came stateside as a member of the Mariners organization, he was known as David Arias, his maternal last name. After three seasons in Seattle’s system, he was traded to the Minnesota Twins, where be began going by David Ortiz, his paternal last name. After spending almost a full season in the Twins’ farm system, Ortiz made his MLB debut in 1997. After six up-and-down seasons in Minnesota, Ortiz was released from his contract. He signed with the Boston Red Sox in 2003 and the rest is history. Big Papi helped break the Curse of the Bambino in 2004, and led the team to World Series titles again in 2007 and 2013, before announcing he would retire following the 2016 campaign. He finished his career with ten All-Star nods, an A.L. MVP, and seven Silver Slugger awards to his name. Possibly the best DH to ever play, Ortiz has a good chance of going to Cooperstown once he is eligible in 2021.
Since Ortiz’s career ended six months ago, he has spent most of his time on philanthropy. He runs the David Ortiz Children’s Fund, which was founded in 2007, and has also recently been a brand ambassador for UNICEF’s Kid Power Champion mission in Burkina.