Red Sox: Theo Epstein drops fascinating “What If” about 2010 trade

A 2010 trade could have turned out much better for the Red Sox.

Theo Epstein was the mastermind behind several franchise-altering moves as the architect of multiple championship teams but one of the final big splashes that he made during his tenure with the Boston Red Sox could have turned out much differently.

Epstein recently announced that he was stepping down as president of baseball operations for the Chicago Cubs. He spoke with the media in the wake of this stunning decision and that naturally led to reminiscing about the past. One topic focused on Anthony Rizzo, the star first baseman for the Cubs who is tied to the legacy of Epstein with two different franchises.

While serving as general manager for the Red Sox in December 2010, Epstein made a deal with the San Diego Padres to acquire All-Star first baseman Adrian Gonzalez for a package of prospects headlined by Rizzo. Gonzalez was productive in Boston so the trade worked out fine for them but it could have been drastically better with one tweak Epstein tried to make.

According to the Boston Globe’s Alex Speier, Epstein wanted to hold on to Rizzo and offered first base prospect Lars Anderson instead. Padres GM Jed Hoyer wouldn’t budge on his demand for Rizzo, forcing Epstein to eventually relent by including his top prospect in order to seal the deal.

Epstein’s offer wasn’t nearly as ridiculous as it appears in retrospect. Anderson was one of the top prospects in the Red Sox farm system at the time but he never panned out. He appeared in only 30 major league games over the span of three seasons, hitting .167 with a .455 OPS.

Hoyer was wise to hold out for Rizzo. He was considered one of the top position-player prospects in the game and eventually lived up to that pedigree. Rizzo is a three-time All-Star, four-time Gold Glove Award winner and has a Silver Slugger on his resume.

None of those accolades were achieved in a Padres uniform though. By 2012, Epstein had left Boston for Chicago where he swung a deal to re-acquire his former top prospect in a trade that sent Andrew Cashner to San Diego.

The move backfired for the Padres when Cashner failed to develop into the ace they hoped for. He spent five solid yet unspectacular seasons in San Diego before bouncing around the league as a veteran journeyman.

Perhaps Epstein tries to pry Rizzo away from Boston if the prized prospect remained in their organization after he left them for Chicago but there’s no telling if Ben Cherington would have made the same mistake that the Padres did. If they wouldn’t give up Rizzo for Gonzalez, we have to assume they wouldn’t do it for Cashner even with the regime change.

Rizzo emerged as a star in Chicago, playing a pivotal role in bringing the Cubs their first World Series title in over a century. A fair case can be made that the Cubs don’t win that title in 2016 without Rizzo, leaving their passionate fan base toiling away in misery.

More from Red Sox News

• Bizarre trade deadline comes back to haunt Red Sox after Nathan Eovaldi departure
• Red Sox’ Moneyball-style offseason continues with Corey Kluber contract
• Rich Hill’s Red Sox departure puts him within striking distance of unique MLB record
• Red Sox offseason takes another nasty hit with Nathan Eovaldi departure
• Why Red Sox fans should be rooting for Carlos Correa’s Mets deal to go through

As for the Red Sox, they got their man in Gonzalez even if the price was steeper than Epstein would have preferred. Gonzalez delivered an All-Star campaign in his debut season in Boston but his true value would end up being as bait for a blockbuster trade with the Los Angeles Dodgers.

Trading a top prospect for what turned out to be fewer than two full seasons of Gonzalez doesn’t seem ideal. However, it proved worthwhile when you consider that Gonzalez was the price to unload malcontents Carl Crawford and Josh Beckett along with nearly a quarter of a billion dollars in long-term payroll in the Dodgers deal. Boston would have been stuck with those bloated contracts if they didn’t have Gonzalez to entice the Dodgers and clearing that much payroll allowed the Red Sox to revamp the roster for a World Series run in 2013.

Adding Rizzo to the mix wouldn’t hinder Boston’s championship chances that year. The Red Sox took a steep dive to the bottom of the division over the next two seasons which coincided with Rizzo’s emergence as an All-Star. His presence in the lineup would have improved the team’s fortunes through those bleak years.

Having a young slugger to build around in an improved offense may have limited the need to chase high-priced free-agents such as Hanley Ramirez and Pablo Sandoval, both of whom were disasters in Boston. The Red Sox were desperate to add star power to bounce back from a miserable 2014 season but they may not have been in that position with Rizzo on the team.

Lars Anderson became one of the biggest prospect busts in recent franchise history but the Red Sox tried to sell high on him while they could. Reymond Fuentes and Casey Kelly never thrived in the big leagues either so Boston’s trade with the Padres would have been an absolute heist if Epstein managed to convince them to take Anderson instead of Rizzo.

Epstein bringing this story up a decade later suggests that he felt he was close to getting the deal done with Anderson and still holds some regret that he had to part with Rizzo instead. At least he rectified that decision when he brought Rizzo to Chicago.

It worked out in the end for the Red Sox and they have the banner to prove it but we can’t help but imagine how the outlook would have improved if they managed to keep Rizzo out of that 2010 trade.