The San Diego Padres have made numerous bold trades over the years, some of which have significantly benefited the franchise. However, not every deal has gone according to plan. From trading away future stars to acquiring risky veterans, these missteps have left fans wondering about what could have been. Here’s a look at five of the Padres’ most regrettable trades since 2000.
The Five Worst Padres Trades of the Century
5. Jason Bay to Pittsburgh (2003)
In August 2003, the Padres traded Jason Bay, Óliver Pérez, and Cory Stewart to the Pittsburgh Pirates in exchange for Brian Giles. At the time, Giles was a proven star, and the Padres hoped he could anchor their lineup as they transitioned to Petco Park. While Giles performed respectably in San Diego, the long-term outcome favored Pittsburgh.
Bay won the 2004 NL Rookie of the Year and became a two-time All-Star with the Pirates, showcasing consistent power and production. Pérez, though inconsistent, had a standout 2004 season with a 2.98 ERA and 239 strikeouts. In contrast, Giles struggled to meet expectations, with declining power and limited playoff impact during his tenure.
4. Corey Kluber to Cleveland (2010)
The Padres sent Corey Kluber to the Cleveland Indians (now Guardians) as part of a three-team deal to acquire Ryan Ludwick, aiming to bolster their offense for a playoff run. Unfortunately, this trade turned into a disaster. Ludwick hit just .228 during his brief time in San Diego before being traded again.
Meanwhile, Kluber evolved into one of the decade’s top pitchers, winning two AL Cy Young Awards and anchoring Cleveland’s rotation. He led the team to the 2016 World Series and delivered years of elite performance, making the Padres’ decision to let him go particularly painful.
3. Adrián González to Boston (2010)
Hometown star Adrián González was traded to the Boston Red Sox for Anthony Rizzo, Casey Kelly, Rey Fuentes, and Eric Patterson, marking a rebuilding phase for the Padres. While González thrived in Boston with 42 home runs and 203 RBIs over two seasons, the Padres failed to capitalize on their return.
Rizzo, one of the key pieces, was traded away shortly afterward in another regrettable deal (detailed below). González’s departure left a void in the Padres’ lineup, and seeing him later excel with the rival Los Angeles Dodgers added to the sting. This trade exemplified the Padres’ challenges in retaining homegrown talent.
2. Anthony Rizzo to Chicago (2012)
In January 2012, the Padres traded Anthony Rizzo and Zach Cates to the Chicago Cubs for Andrew Cashner and Kyung-Min Na. While Cashner showed flashes of potential, his Padres career was marred by injuries and inconsistency.
Rizzo, however, became a cornerstone player for the Cubs, earning three All-Star selections and playing a pivotal role in their historic 2016 World Series win. Losing Rizzo cost the Padres a franchise-defining talent at first base and forced them to watch him achieve success elsewhere.
1. The 2014 Offseason
The A.J. Preller era began with a series of aggressive trades that ultimately backfired. Among these, the Padres sent Trea Turner to the Washington Nationals (as part of a three-team deal for Wil Myers) and Max Fried to the Atlanta Braves (in a trade for Justin Upton). They also acquired Matt Kemp from the Dodgers in exchange for Yasmani Grandal, Joe Wieland, and Zach Eflin.
Los Angeles Dodgers.
Turner became an electrifying All-Star shortstop and World Series champion, while Fried developed into an ace and a key figure in Atlanta’s 2021 title run. Meanwhile, Myers, despite being a fan favorite, struggled with inconsistency, and Kemp’s production didn’t justify his hefty contract. Grandal, on the other hand, became an All-Star catcher for the Dodgers. These moves remain a sobering reminder of the risks of high-stakes trades.
Honorable Mention: The Juan Soto Trade (2022)
This blockbuster trade initially thrilled Padres fans but ultimately fell short of expectations. While the team made the NLCS in 2022, Soto was dealt to the Yankees a year later, following a disastrous 2023 season. In the trade, the Padres parted with promising prospects like CJ Abrams, MacKenzie Gore, and James Wood, betting on Soto’s future in San Diego.
The plan hinged on re-signing Soto, but his eventual $765 million deal with the Mets was far beyond the Padres’ reach. Although the team flipped Soto for Michael King, Dylan Cease, and Kyle Higashioka, the long-term impact remains uncertain. Time will tell if this trade is seen as a calculated gamble or a costly blunder.
About The Author
Leave a Reply