While we talk about some of the worst teams we’ve ever seen, like the 2025 Colorado Rockies or the 2024 Chicago White Sox, the franchise that has the most losses ever is the Philadelphia Phillies. For decades, the Phillies have been known as a lovable loser. The Phillies have lost more than 11,000 games in its history, more than any other team in MLB history.
Yet, that’s not how we look at the Phillies today. Now, they are one of the most star-studded teams in the league. In the 21st century, the Phillies have won the National League pennant three times and they’ve won the NL East title six times. They even won their second World Series title in 2008.
Today, there are stars in the lineup and a chance to compete every year. It’s a much different team than in years past, but that doesn’t mean we should forget the past. There have been all-time greats who have played in the City of Brotherly Love. Many are retired now, but some are still building their Philadelphia legacy.
First Base
Ryan Howard
2004-2016
Ryan Howard had a stretch where he was one of the most feared hitters in baseball. His early career was some of the best power hitting we’ve seen from a youngster this century. He won the Rookie of the Year award in 2005 after hitting 22 home runs and adding 63 RBIs. That was just an appetizer.
The Phillies saw one of the best seasons in the history of the franchise with Howard’s 2006 season. He won the National League MVP after hitting a league-leading 58 home runs and putting up a 149 RBIs. He dominated the field, becoming the best slugger in baseball at a time that included David Ortiz, Albert Pujols, and Lance Berkman.
Howard continued his success, adding more than 130 RBIs in each season from 2006 to 2009. In three of those four years, Howard led baseball in RBIs. He would continue to put up big numbers until 2011, but injuries started to catch up to him. He would miss time throughout the rest of his Phillies career.
However, Howard left behind a great legacy. He was a great slugger who could hit the ball a mile. It is unfortunate how it all ended, but Howard did bring a World Series to Philadelphia, and that legacy will last a lifetime.
Second Base
Chase Utley
2003-2015
Sticking with this era of Phillies baseball off the top, Chase Utley is hard to top for fan favorites in baseball. Like Howard, Utley had a window where he was one of the best in the league at his position. He made five-straight All-Star Games and added four-straight Silver Slugger awards at second base.
Utley was a major component of the Phillies team that went to the World Series in back-to-back years. He had three home runs, nine RBIs, and three stolen bases during their 2008 championship run. He only hit .220 that year, but he had a .391 on-base percentage, making sure there were players on base for the power hitters behind him. Utley was even better in the 2009 playoffs, putting up six home runs, a .292 average, and 15 runs. He had five home runs in the World Series, a record he shares with Reggie Jackson and George Springer.
Utley once held the MLB record for reaching base in 27 consecutive playoff games. The record has since been broken by Miguel Cabrera. It shows the insane consistency that Utley brought to the Phillies for so many years.
This was a player born for Philadelphia. He did not care what his opponents thought of him as long as he was winning. He would kick up dirt, slide through opponents, and go full throttle on every play just to gain that extra inch to give his Phillies the advantage.
Shortstop
Jimmy Rollins
2000-2014
Why don’t we stay right here in the mid-2000s as we assess the great career of Jimmy Rollins? The Phillies’ long-time shortstop was outstanding for more than a decade. Rollins brought a little bit of everything to the lineup. He had surprising power numbers, could steal bases every time he got on base, and he led the league in triples four times. He was the ultimate mixture of speed and power. Rollins added great value to the Phillies' lineup.
In 2007, Rollins won the NL MVP. He was incredible that season. In the 21st century, only Curtis Granderson had more triples than Rollins, who had 20. He also had a league-leading 139 runs, 30 home runs, 94 RBIs, and 41 stolen bases.
He was even a great fielder at the hardest position on the field. He won the Gold Glove four times. No Phillies player has won a Gold Glove since Larry Bowa did it in 1978. Rollins ended that streak, truly proving this was a different era of Phillies baseball.
Rollins is the Phillies' career leader in at-bats (8,628), hits (2,306), doubles (479), and second in games played (2,090) and stolen bases (453), and third in runs scored (1,325) and triples (111). He did all this while playing some of the best shortstop in the league. He helped the Phillies get back to the World Series and brought Philadelphia their first title in any sport in decades. This city will love Rollins for his contributions to baseball and to the Philadelphia.
Third Base
Mike Schmidt
1972-1989
There are few players in the league who have had as big an impact on one franchise as Mike Schmidt. He is the catalyst for Philadelphia Phillies players. While almost every other superstar player in the Phillies organization eventually left, Schmidt was different. He was truly married to the city of Philadelphia, staying with the franchise through sickness and health.
Schmidt spent 18 years with the Phillies, hitting 548 home runs and knocking in close to 1,600 runs. There is really no argument to be made for any other Phillies third baseman. Schmidt is worlds better than everyone else.
Now the real question is if Schmidt is the best third baseman of all time. There’s an argument to be made that he’s the top guy at the position. Yes, there are other superstars like Brooks Robinson, Alex Rodriguez (who also played shortstop), George Brett, and Eddie Matthews, but Schmidt leads all of them in bWAR while playing third base. Schmidt finished his career with 106.4 bWAR.
Today, he’s one of the most underrated power hitters in the history of the game, and he chose Philadelphia for his entire career.
Catcher
Darren Daulton
1983-1997
This was a real competition. There are three Phillies catchers who stand out. Bob Boone, who was one of the better defensive catchers of his era, was the Phillies backstop throughout the 1970s. Their current catcher J.T. Realmuto might take this over in just a season or two, performing as one of the best offensive catchers in the game today. He’s actually been with the Phillies for seven years, which may shock some people.
However, for now, we’re going with Darren Daulton. He was a center-of-the-lineup guy for those 1980s and 90s Phillies teams. He was behind the plate every single day, and he could go yard when the Phillies were desperate for offense. This wasn’t a great era of Phillies baseball, as he only made the postseason once. He did get to win a World Series after he was traded towards the end of his career to the Marlins, and he hit .364 in the postseason that year. If he wasn’t so committed to Philadelphia, we might see his career differently.
Daulton was always pushing for more, and he had this great stretch from 1992 to 1995 where he made three All-Star teams and led the league in RBIs with 109 in ‘92. He won the Silver Slugger that year and finished sixth in MVP voting. His radio show extended his legacy in Philadelphia, and while Realmuto is likely to pass him, he still holds onto this distinction as the best catcher in team history.
Right Field
Bobby Abreu
1998-2006
Bobby Abreu played for the Phillies at a strange time in Philadelphia sports. The rise of the internet, daily local radio shows, and a long history of disappointment from the four major sports had Philly fans angrier at their stars. Donovan McNabb received the brunt of the vitriol, as he couldn’t get the Eagles over the hump, but stars in other sports like Allen Iverson, John LeClair, and Bobby Abreu faced their own set of expectations that many believed weren’t met.
Abreu was actually really good for a stretch. But because of the struggles of the Phillies overall, he is now underrated. Abreu had deceptive speed and good power. He was a guy to put in the middle of the lineup, where he was more than 150 games every season. He even played all 162 games twice for the Phillies.
He won a Gold Glove in 2005 and a Silver Slugger in 2004. He led the league in doubles in 2002 and in triples in 1999. His stat line included more than 40 doubles five times. Abreu broke 20+ home runs seven times with Philadelphia, including two seasons where he had 30+ home runs. That speed we talked about also came through on the base paths, where he had 30 stolen bases five times. He even had 40 stolen bases once!
If the Philadelphia Phillies were any better and if Abreu were better with the media, he would have been beloved by this fanbase and would have been more in consideration for awards as well.
Center Field
Richie Ashburn
1948–1959
Richie Ashburn played in an era with the greatest players of all time. Mickey Mantle, Willie Mays, Jackie Robinson, Stan Musial, Duke Snider, and Roy Campanella were all working for attention. Ashburn still stood out for his style of play, his effort in each at bat, and his impact to the Phillies. In what has become a theme, he would have had more glory if the Phillies were just a better team, but he did just fine during his tenure in the league.
Ashburn finished his career with 2,200 hits over 12 years in Philadelphia. He won two batting titles and finished his career with an over .300 batting average. He also understood the importance of getting on base, leading the league in walks three times with the Phillies. This is the type of player that would have been successful in any era. Ashburn was the first player ever to win the batting title and lead the league in walks.
At the end of his career, Ashburn was considered one of the best leadoff hitters of all time, and he was great in center field. He clearly took pride in the details of the game, because he was so into making sure every aspect of his game was clean. This is the type of player a manager begs for.
Left Field
Ed Delahanty
1891-1901
We have to be honest, we haven’t had many, if any, players who played most of their careers in the 19th century. It was a completely different game then. However, the Philadelphia Phillies had a few really good players back then. This one deserves to be in this lineup.
You may not know Ed Delahanty, but he was one of the first power hitters in the history of the game. He hit his 100th home run right after the turn of the century, which had him up there with the all-time home run hitters for decades. He was tied with Honus Wagner in the eighth spot on the all-time list until 1918. In 1919, he was passed by Babe Ruth, who would own the all-time home run lead by the end of the next season.
He wasn’t just a power hitter. Delahanty hit over .400 three times in his career. In 1896, he became the second person ever to hit four home runs in a game. Still, to this day, he’s the only player to have one game with four home runs and one game with four doubles.
Delahanty played in the league almost 150 years ago, but he was so good that he’d probably be a decent player today. After his career ended, Delahanty tragically died after an accident in the Niagara River, and many believe he may have fallen down Niagara Falls.
Designated Hitter
Bryce Harper
2019-2025
Skipping ahead to today, Bryce Harper is one of the best power hitters of this era, and he’s the best free agent acquisition in the history of this franchise. Taking him from their rivals just a few miles away in Washington, D.C., Harper signed a 13-year, $330 million deal in March 2019. Looking at what Juan Soto signed for just a few months ago, this seems like the bargain of the century.
Harper has been dominant for the Phillies over his six-plus years. He won the NL MVP in 2021 after leading the league in slugging percentage and OPS, among multiple other categories. He led the Phillies to the World Series in 2022, winning NLCS MVP along the way. That postseason, he hit .349 with six home runs and 13 RBIs.
It’s been a while since the Phillies were perennial contenders like they are now. You have to remember, the Phillies didn’t win a postseason series until 1980, the year they won their first World Series. They only have 15 playoff series wins in the history of the franchise. Harper was responsible for five of those series wins, a third of the team’s history in just six seasons.
Harper is looking to keep the magic alive, as the Phillies are in the driver’s seat to win the National League East and go on another run towards the World Series. By the end of his contract, Harper has a real chance to be the best player outside Schmidt to ever wear a Phillies uniform.
Starting Pitcher
Steve Carlton
1972-1986
The Philadelphia Phillies have had their share of great starting pitchers. Heck, at one time they had Roy Halladay, Cliff Lee, Cole Hamels, and Roy Oswalt in the same rotation. Yet, despite the talent the Phillies have had in the rotation, including today with Aaron Nola and Zack Wheeler, there was no other choice for starting pitcher here than Steve Carlton.
One of the most underrated pitchers in modern baseball history (again, a theme for Philadelphia), Carlton was a flamethrower with a unique motion that fooled hitters to the tune of 4,136 strike outs over his career. More than 3,000 of those strike outs came as a member of the Phillies. He was the best pitcher in baseball, and he had the hardware to back it up. He won four Cy Young awards in Philadelphia, the first player in baseball history to do it.
Carlton’s best season came at the right time. In 1980, he had a 10.2 WAR, leading all of baseball, along with 24 wins to only nine losses and 286 strike outs. He would lead the Phillies to the playoffs that season, where he kept the good times rolling. He went 3-0 with a 2.30 ERA in the postseason, helping secure the first World Series title in franchise history.
To think, the only reason Carlton was even on the Phillies was out of spite. The St. Louis Cardinals GM traded him to a last-place team because of a salary dispute in 1971, and now he took his legacy to the City of Brotherly Love, where he excelled. Who knows how many more titles the Cardinals have with the best pitcher in baseball in their rotation? Instead, glory came to Philadelphia.
Relief Pitcher
Brad Lidge
2008-2011
It was really hard to leave Tug McGraw off this list for his longevity and impact to the Phillies for a decade in the ‘70s and ‘80s, but there is no greater impact than that of Brad Lidge, who was the Phillies final pitcher when they won the World Series in 2008. Lidge came to the Phillies in a trade the offseason prior, with the Astros moving him for Michael Bourne and a few other pieces.
In his first season in Philadelphia, Lidge was perfect. No, literally, Lidge was given 41 save opportunities, and he had 41 saves. It changed the Phillies bullpen overnight. Now, this was a team ready to compete in the postseason. He even received first-place votes for MVP. As a closer.
He continued that dominance in the postseason, saving seven games in seven opportunities on the way to the Phillies’ second World Series title. He finished Game 5 of the World Series with a strikeout, a fitting end for one of the best seasons we’ve seen from a closer in any franchise.
Lidge would continue his run with the Phillies, including another World Series appearance in 2009. He was bad during the regular season, but he rebounded in the playoffs in the Divisional and Championship Series. He stayed there through the 2011 season, but he never hit the highs of the 2008 season. Luckily, it ended with a ring.