Billy Beane once famously referenced Branch Rickey when he said, “It’s better to make a trade a year too early than a year too late.” The notion is that, if you wait too long, you’ll miss the ideal window for trading a veteran MLB player for prospects that are good enough to restock your farm. One example of a team that failed to heed this advice was the Phillies, circa 2011. And their story may have implications for a team in a similar boat today – like the Astros.

So let’s take a look back at the case of that Phillies team, and the moves they made – and should have made.

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After winning a long-awaited World Series in 2008, and returning to the Fall Classic the following year, the downfall of the Phillies was a precipitous one. An NLCS exit in 2010 begat an NLDS knockout in 2011, and the team then failed to make the postseason over the following decade. 

Things seemed doomed from the start when then-General Manager Rubén Amaro Jr. stubbornly refused to steer the floundering franchise into a rebuild, holding on to his aging stars well past their sell-by dates.

Making things worse, player development was a big problem during the club’s ensuing decade-long run of incompetence, with right-hander Aaron Nola and first baseman Rhys Hoskins being the only homegrown players of note.

Ultimately, Amaro traded away his franchise icons years after it was clear the team needed to reset, getting back packages of varying degrees of quality. Some players, like Cole Hamels and Jimmy Rollins, brought in decent returns, while others, like Chase Utley and Carlos Ruiz netted barely anything at all. 

Let’s jump into some of the more noteworthy trades from the Phillies’ descent into futility, and see when they struck while the iron was hot, when they waited far too long, and when trading away a star didn’t make any sense at all.

 

Cliff Lee

Looking to capture a second consecutive World Series trophy in 2009, newly-minted Phillies’ GM Amaro decided to reel in a true ace for the team’s postseason push. Reigning AL Cy Young Award winner Lee was on the block that summer, and Amaro parted with four exciting prospects to get a deal done: Carlos Carrasco, Jason Donald, Lou Marson and Jason Knapp. 

Donald and Marson failed to produce much at the big-league level, and Knapp never reached the majors. But Carrasco made it worthwhile for the then-Cleveland Indians, turning in 11 excellent seasons in Cleveland’s rotation. The deal was well worth it for the Phillies, however, as Lee made 12 starts down the stretch, posting a 3.39 ERA and anchoring the club’s rotation on their way to the National League pennant.

Seeking to bounce back from a gut-wrenching World Series loss, Amaro swung another deal for a top-tier starter, acquiring future Hall of Famer Roy Halladay from the Blue Jays. With Halladay now in the fold, the decision was made to flip Lee in his last year of team control for future assets to improve the team’s long-term outlook.

So Lee was moved to the Mariners for a trio of prospects: outfielder Tyson Gillies, and right-handers Phillippe Aumont and JC Ramírez. 

The Phillies bowed out of the playoffs with a Championship Series loss to the Giants, and a Divisional Series loss to the Cardinals in 2011 ended their Howard-Utley-Rollins heyday. As for the three youngsters they received in exchange for Lee, none of them panned out.

Aumont hung around Philly for parts of four seasons, appearing in 46 games and posting a wretched 6.80 ERA and -0.4 fWAR. Ramírez was somehow worse, posting a 7.50 ERA and -0.6 fWAR over 24.0 innings in his lone season in Philadelphia. Gillies failed to make the major leagues, and the Phillies cut him loose after the 2014 season.

So the Phillies turned down a chance at an all-time great rotation featuring Halladay, Lee and Cole Hamels, and got less than nothing to show for it. In exchange for Lee’s 7.3 fWAR in his last season of team control, the Phils received three prospects who totalled -1.0 fWAR during their time with the team. 

That massive swing-and-miss not only marked a missed opportunity to either put together an otherworldly starting rotation or add actual difference-making young talent to the farm system, but was also the beginning of the end of perhaps the franchise’s greatest era.

 

Shane Victorino

Victorino was a quality center fielder over his eight years in Philadelphia, earning two All-Star berths and three Gold Gloves while slashing .279/.345/.439 across 3,977 plate appearances. The Flyin’ Hawaiian had taken a bit of a step back in 2012, posting a .261/.324/.401 line in 431 trips to the plate with the Phils, and was in the last season of a three-year, $22 million extension he signed heading into 2010. With free agency looming, Amaro decided to flip the fan favorite to the Dodgers in summer 2012 for some future help.

In exchange for two months of Victorino’s services, the Phillies received 25-year-old right-hander Josh Lindblom and 23-year-old starting pitching prospect Ethan Martin, as well as a player to be named later, who wound up being lottery ticket infielder Stefan Jarrin.

That package proved to be wholly underwhelming, as all three players barely made any impact for the Phillies. Lindblom appeared in 26 contests during his one season in Philadelphia, working to a 4.63 ERA across 23.1 innings pitched. In December 2012 he was traded to Texas alongside Lisalverto Bonilla in exchange for an aging Michael Young. 

Despite some initial buzz surrounding Martin on his rise up the minor league ladder, injuries and ineffectiveness limited the burly righty to 44.0 innings pitched in 17 big league games. 

Jarrin, who had spent his first two professional seasons in Rookie ball, never even appeared in a minor league game after the trade.

All in all, the Phillies traded away a franchise icon who had racked up 24.0 fWAR over eight seasons in their uniform in exchange for a trio of players that combined for -0.7 fWAR in Philly.

 

Hunter Pence

The Phillies found themselves with a hole in right field in 2011, as All-Star Jayson Werth had departed for the Nationals in free agency the previous offseason. To plug the gap, Amaro sent highly-regarded youngsters Jarred Cosart, Jon Singleton, Josh Zeid and Domingo Santana to the Astros in exchange for two-and-a-half years of team control over Pence, a two-time all-star.

Pence was excellent in 155 games for the Phillies, slashing .289/.357/.486 across 676 plate appearances, and earning 4.0 fWAR. But with a season-and-a-half of team control left, Pence was worth a pretty penny on the trade market, so he was dealt at the 2012 deadline to the eventual World Series-winning Giants for a package headlined by 21-year-old catcher Tommy Joseph, alongside lefty reliever Seth Rosin and fourth outfielder Nate Schierholtz.

The Phillies got 37 games out of Schierholtz before releasing him ahead of the 2013 season, wherein he slashed .273/.319/.379. Multiple concussions ultimately forced the highly-touted Joseph out from behind the dish and over to first base, where he appeared in 249 games for the Phillies, slashing .247/.297/.460 for a 95 WRC+. Rosin bounced around multiple organizations as a Rule V pick before making his big league debut in 2014 with the Rangers. He was ultimately returned to the Phils, where he allowed five earned runs in 2.0 major league innings in his only appearance for the team.

In exchange for the 4.7 fWAR that Pence posted from the 2012 deadline to the end of 2013, the Phillies received a trio of players that wound up giving them a whopping -0.5 fWAR. Considering Pence’s status as a franchise icon for the Giants, and the Phillies’ pitiful trade return, this one goes down as a truly horrific fleecing.

 

Jimmy Rollins

The 2013 season was a rough one for the Phillies, as the organization parted ways with World Series-winning Manager Charlie Manuel in the midst of a 73-89 campaign. 2014 was more of the same, as the team posted an identical win-loss record. 

Shortstop Rollins was the face of the franchise for years, and one of the most important elements of the Phillies’ 2008 championship team. The 2007 NL MVP had steadily declined after their World Series win, posting a cumulative .252/.318/.397 line from 2009-2014. With the club foundering and their former star in his last year of team control, the decision was finally made to deal him.

The Dodgers found themselves with a hole at shortstop, as three-time All-Star Hanley Ramírez had departed for the Red Sox in free agency. On December 19, 2014, the Phillies traded Rollins to the Dodgers in exchange for minor league hurlers Tom Windle and Zach Eflin. Windle spent five seasons in the Phillies’ system, reaching as high as Triple-A, but failing to make the majors before finding himself out of affiliated ball after the 2021 season. Eflin, however, made this deal a big win for the Phils.

A 2012 first-round pick by the Padres, Eflin was flipped to the Dodgers as part of the ill-fated Matt Kemp deal in the 2014-15 offseason, and was then used to acquire Rollins the following day. Eflin made his major league debut on June 14, 2016, and would go on to post a respectable 4.49 ERA over 659.1 innings in seven seasons in Philadelphia. 

Eflin missed a good deal of the 2022 season with knee injuries, but came back as the team’s de facto closer during their miracle pennant-winning run. He signed a three-year $40 million pact with the Rays prior to 2023, and had his best season to date last year with a 3.50 ERA across 177.2 innings of work.

As for the Dodgers’ end of the deal, Rollins struggled to a .224/.285/.358 slash in 563 plate appearances in his lone season in Los Angeles. He went on to appear in 41 games for the White Sox in 2016 before retiring at the age of 37.

All told, the Phillies made out like bandits in this one, trading away Rollins, who accumulated only 0.4 fWAR as a Dodger, in return for 8.7 fWAR from Eflin’s seven seasons.

 

Cole Hamels

2008 World Series MVP Hamels was one of the best pitchers in Phillies history, working to a 3.30 ERA in his 10 seasons with the team. The 31-year-old lefty was his usual self through 20 starts heading into the 2015 trade deadline, posting a 3.64 ERA over 128.2 innings. 

Hamels had signed a six-year, $144 million extension prior to 2013, and had three-and-a-half seasons of team control remaining, not including a vesting option for 2019. With such a valuable player spinning his wheels on a 39-64 team heading into July 31, the decision was made to part with one of the franchise’s cornerstones.

The Phillies initially sought to trade Hamels to the up-and-coming Astros, but the southpaw used his no-trade clause to block the move to Houston. Instead, the Rangers came calling with an impressive package of young talent.

The Rangers parted with well-regarded catching prospect Jorge Alfaro, sweet-swinging outfielder Nick Williams, and young hurlers Alec Asher, Jerad Eickhoff and Jake Thompson, as well as former All-Star starter Matt Harrison in exchange for Hamels and lefty reliever Jake Diekman.

Hamels was as good as advertised in Texas, tossing 546.2 innings of 3.90 ERA ball in his four seasons with the Rangers before being flipped to the Cubs at the 2018 deadline for swingman Eddie Butler and two minor leaguers. Diekman also ended up being a valuable addition for the Rangers, firing 124.1 innings of 3.18 ERA work in his four years in Arlington.

On the Phillies’ side, it wasn’t a disaster by any means, but they didn’t end up with the franchise-altering haul of young talent they had hoped for. Williams opened eyes with a 110 WRC+ in his 83-game rookie season in 2017, but failed to make good on that promise in his next two seasons, and was out of the big leagues after 2019. He made a four-game cameo with the White Sox in 2021, but hasn’t reached the majors since.

Eickhoff had a decent, if unspectacular, five-year run in Philadelphia, piling up 440.0 innings with a 4.15 ERA while being hampered by injuries along the way. He’s bounced around multiple organizations in the years since, failing to make a significant impact anywhere.

Thompson only made his way into 30 big league contests scattered across three seasons, all with the Phillies. The 6’4” right-hander totalled 116.1 innings with a 4.87 ERA before finding himself out of the majors for good after 2018.

Asher only started 12 games for the Phillies, putting up a woeful 5.88 ERA over 56.2 innings. He wasn’t much better in 24 games for the Orioles, and saw his last MLB action in 2018 with a two-game cup of coffee with the Brewers.

Spinal fusion surgery ended Harrison’s 2014 season early, and looked to be the end of his MLB career. He gutted out three appearances for the Rangers in 2015, but was shut down on July 27 due to another back flare up. With his hopes of ever taking the mound again at virtually zero, he was included in the Hamels deal solely to offset some salary, and never wound up pitching in the majors or minors again.

The most fruitful part of the trade for the Phillies was Jorge Alfaro, who acquitted himself well in his 143 games with the Phillies, slashing .270/.327/.422 across 508 plate appearances. More importantly, the Colombian-born backstop was packaged with minor leaguer Will Stewart and number-one prospect Sixto Sánchez to acquire All-Star J.T. Realmuto from the Marlins ahead of the 2019 season, who went on to become arguably the best catcher in baseball.

From an fWAR perspective, this deal lands almost dead even, with the Phils getting a cumulative 8.9 mark from their six-player haul, while the Rangers squeezed 8.7 out of Hamels and Diekman. However, the fact that Alfaro was a key piece in bringing in Realmuto for the Phillies’ recent resurgence puts this trade firmly in the win column.

 

Chase Utley

Less than a month after the Hamels trade, Amaro dealt another Phillie who is destined to have his number retired. Second-baseman Utley had been a pillar of the coming-of-age Phillies teams of the late 2000’s, racking up six All-Star nods and four Silver Slugger Awards in 13 seasons with the team. However, injuries and age had taken their toll on the 36-year-old, and he had slashed a measly .217/.284/.333 across 282 plate appearances for the Phils in 2015. With the organization fully in tank mode, and Utley signed to a one-year, $15 million deal, the decision was made to finally flip the veteran for whatever assets could be had.

Utley’s hometown Dodgers placed a waiver claim and worked out a deal for 24-year-old utilityman Darnell Sweeney and 22-year-old right-hander John Richy. He posted a modest 0.3 fWAR for the Dodgers in 34 contests after the 2015 trade, and went on to play three more seasons in Los Angeles after 2015, slashing .236/.315/.381 over 1,246 trips to the plate, and helped the club take home the National League pennant in 2017.

Neither prospect Philadelphia received amounted to much, with Sweeney appearing in 37 games in his lone season in Philadelphia, posting an awful .639 OPS over 98 plate appearances. He made a two-game guest appearance with the Blue Jays in 2018 before being out of the big leagues for good. Richy never made it past Triple-A, bringing the Phillies’ total fWAR from this deal to -0.4. 

Sweeney was sent back to the Dodgers after the 2016 season alongside Darin Ruf in exchange for Howie Kendrick, who had an excellent 39-game stretch in Philadelphia before being flipped to the Nationals for minor league hurler McKenzie Mills. Overall, the Phillies got very little value for a potential Hall of Famer after waiting far too long to trade him away.

The franchise second-baseman posted WRC+ marks of 114, 126 and 107 in 2012, 2013 and 2014, respectively, as opposed to the ugly mark of 64 he had as a Phillie in 2015. If Amaro had pulled the trigger on an Utley trade only a season or two earlier, he undoubtedly could’ve secured a much better return.

 

Carlos Ruiz

One year after the Utley trade, the Phillies and Dodgers linked up for another waiver-wire deal, this time for a former All-Star catcher. Carlos “Chooch” Ruiz had been an anchor for the Phils since 2007, posting a solid .266/.352/.393 line across 3,884 plate appearances, while providing excellent defense. However, the Panamanian was on his last legs in 2016, putting up a .719 OPS in only 48 games for the Phillies.

On August 25, the Dodgers parted with longtime backup catcher A.J. Ellis, minor league starter Tommy Bergjans and a player to be named later for Ruiz’s services for the stretch run. A few weeks later minor league outfielder Joey Curletta was sent to the Phillies to complete the deal.

Ruiz appeared in only 14 games during his brief time in L.A., earning a .683 OPS over 40 plate appearances. In November of that year he was flipped to the Mariners for journeyman reliever Vidal Nuño III, who never played a game in Dodger blue.

Similarly, Ellis only suited up for 11 games for the Phillies, but posted a very nice .871 OPS in that span. He left for the Marlins in free agency that winter, and finished out his career with the Padres in 2018. Bergjans and Curletta both failed to reach the big leagues, making this essentially a one-month swap of backup catchers for the two teams. Technically, the Phillies got the better end of it, with Ellis’ 0.2 fWAR for them edging out Ruiz’s 0.1 for the Dodgers, but this is another instance of the Phillies waiting far too long to deal a once-valuable player.

At 37, Ruiz was only a shell of his former self, having caught 48 games for the Phils in 2016 and only 86 the year before. However, a decent return could have been secured if Amaro had pulled the trigger on a deal as late as 2014, when Ruiz posted a 106 WRC+ over 110 games, or even 2012, when he earned an All-Star nod with an excellent 152 mark in 114 contests.

 

Conclusion

Savvy teams like the Rays have gained reputations for being able to remain competitive almost in perpetuity. A large part of the Rays’ success has been knowing when to trade expiring assets for younger ones. Many aging stars have been turned into impact prospects over the years –   flipping Matt Garza to the Cubs netted Chris Archer; dealing Archer to the Pirates landed Tyler Glasnow, Shane Baz, and Austin Meadows, and this winter’s trade of Glasnow to the Dodgers brought in Ryan Pepiot.

The Phillies had no such luck in their quest to rebuild, as they failed to bring in enough talent to help the team make its way back to contention in a timely manner. Waiting too long to cash in aging stars like Utley and Ruiz, and failing to get sufficient returns for players at their peaks, like Lee and Pence, killed precious opportunities to inject much-needed talent into the minor league system.

With bloated contracts and an aging roster, the Phillies weren’t able to maintain their World Series-caliber peak for long. Player development was the biggest thorn in their side, as top prospects like Dominic Brown, Cody Asche and Maikel Franco, among others, failed to turn into the stars the team envisioned. 

However, the trades they made, or lack thereof, did little to help their cause. If the Phillies had taken a page out of the Rays’ book, and dealt their most significant assets when they still had high value, instead of clinging to fading hopes of contention, they could’ve avoided over a decade of miserable baseball.