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Alex Speier

What if the Red Sox did not trade Anthony Rizzo?

Anthony Rizzo was drafted by the Red Sox in 2007.AP

The list of Cubs players and officials with ties to the Red Sox is long, creating an atmosphere and a sort of reunion when the reigning champions spend the next three games in Boston. Theo Epstein and Jon Lester, in many ways, are the headliners of the reunion tour, but many, many others who were part of Red Sox championships will be back as well, from reliever Koji Uehara and 2013 Game 6 winner John Lackey to former Sox assistant GM and current Cubs GM Jed Hoyer and Cubs advisors Kevin Youkilis and Ryan Dempster.

Yet at a time when the Red Sox are struggling desperately to hit for power, and when the team’s Bermuda Triangle at third base continues to yield poor production, a case can be made that the most interesting what-could-have-been involving a Cubs player visiting Boston this weekend is a player who never played in the big leagues for the Sox.


One of the most fascinating questions to ponder in an exercise of revisionist history: What might have happened had the Red Sox not traded Anthony Rizzo in a package that netted Adrian Gonzalez?

There was organizational debate about whether to ship off a package of three key prospects – righthander Casey Kelly was the headliner with Rizzo an obvious second piece given that Gonzalez represented the long-term answer at first base, with 2009 first-rounder Reymond Fuentes also in the deal – while still committing approximately $160 million to Gonzalez in appending a seven-year, $154 million deal to his $6.3 million bargain of an option year in 2011.

“There’s always wrestling in every trade – especially when you give away prospects for talent that’s going to help in the more immediate future,” said Red Sox chairman Tom Werner.

The clearest alternative to dealing for Gonzalez would have been the re-signing of third baseman Adrian Beltre, who was a free agent after a spectacular 2010 season with the Red Sox, and having Kevin Youkilis at first base.


At the time that the Red Sox struck their deal for Gonzalez, it was far from clear that they would be able to bring back Beltre – their initial conversations about a contract framework with agent Scott Boras had suggested that Beltre’s free agency wouldn’t play out quickly, thus leaving the Sox in a position of uncertainty if they did prioritize him. The deal with the Padres, on the other hand, represented a bird-in-hand solution.

Still, had the Sox been able to re-sign Beltre – who proved a bargain for the Rangers at six years and $96 million – they would have been able to keep their prospects – or, perhaps, use them in another deal that would have created a different Choose-Your-Own-Adventure. Epstein acknowledged that as the team juggled offseason variables, there were dramatically different courses it considered – including possibilities that could have kept Rizzo in the Red Sox organization.

“There’s always myriad alternatives. There’s never just one plan,” Epstein said on Friday at “Champions For Charity,” a fund-raising lunch organized by his Foundation To Be Named Later and the Red Sox Foundation. “In an alternate universe, we could have signed Beltre, moved Youkilis to first. We came really close to trading for [outfielder] Carlos Beltran instead of signing [Carl] Crawford. That would have been great, but that kind of got banged on the medicals.


“There’s always a ton of scenarios. But we thought [Gonzalez’s] swing was uniquely suited for Fenway, and we thought he’d be a pretty good offensive force. And ironically, when you look back at 2011, it was a pretty incredible year. All anyone remembers, obviously, is the other side of the coin, but he did perform here. And even now, at the end of the contract, he’s still a productive player.”

The logic of acquiring Gonzalez – who then looked like one of the best hitters in the game – was obvious at the time, and remained so for most of 2011. Moreover, even the way that Gonzalez’s career unfolded with the Red Sox played a significant role in laying the groundwork for the team’s 2013 championship, since he was the key to a deal that allowed the Sox to unload not only his contract but also those of Crawford and Josh Beckett in 2012, freeing extraordinary resources that allowed the Sox to acquire the free agents who proved pivotal in a 2013 title.

That said, as time went on and as Rizzo’s stock continued to rise, it became harder to ignore completely the alternate universe. The fact that Rizzo became one of the first players acquired by Epstein after he took over the Cubs – Chicago landed Rizzo from San Diego in a four-player deal – suggests that Epstein had spent plenty of time scrutinizing the logic of the deal for Gonzalez.

“I had angst about [trading Rizzo] as we were doing it. I told Rizz we were going to trade back for him at some point -- and we did,” said Epstein. “I just happened to be in a different organization.”


For his part, Rizzo still thinks at times on his development in the Red Sox organization, for whom he played from 2007-10, and with whom he went through the life-changing process of recovering from cancer as an 18-year-old in 2008. A player who in many ways became the first cornerstone of the young Cubs core, however, spends little time playing the what-if game.

“The Red Sox drafted me and it was an historic franchise. Little did I know it would be such an amazing franchise as far as the way I was instructed and the way I was treated. I’m glad I got my start there,” said Rizzo. “From time to time, I do [think about the Red Sox]. I enjoyed my time there. That organization taught me a lot. But now I just watch them on TV, that’s really it.”

The Red Sox, on the other hand, can be permitted a brief rumination on what their team might have looked like with Rizzo – one of 11 players in the big leagues with at least 100 homers since 2014 – as their foundational middle-of-the-lineup masher, rather than a player for whom they must account over the next three days.

Peter Abraham of the Globe staff contributed to this report. Follow Alex Speier on Twitter at @alexspeier.