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Inside The Anthony Rizzo Trade That Kickstarted The Cubs' Historic World Series Run

The men behind one of the most compelling challenge trades of the decade tell the story of how it came together.
Ken Blaze-USA TODAY Sports

Perhaps the most remarkable aspect of the Chicago Cubs' World Series-winning roster was—at least on the hitting side—how predictably it came together. While the team's pitching rotation was cobbled together with bric-a-brac from across the baseball spectrum, just about every aspect of the Cubs' offense seemed all but preordained.

Kris Bryant became the franchise-defining player he was billed to be almost immediately after his arrival, while not even a six-month layoff could curtail Kyle Schwarber. Wilson Contreras began the year as the safest bet in the minor leagues to become a solid everyday catcher, and finished the year as exactly that. Addison Russell was supposed to make Oakland rue the day they traded him for trade deadline rentals, and has already turned in a 20-home run season with Gold Glove defense prior to his 23rd birthday. Javier Baez, meanwhile, has been just as up-and-down as his strikeout rates suggested he could be, a dynamic talent still learning how to navigate major league pitching.


In fact, the only piece of the club's young core who didn't progress so smoothly is the one who started everything. Nobody knew what Anthony Rizzo would become in Chicago—much less that a challenge trade between two of baseball's bottom feeders would be the first domino that would propel Chicago to its first World Series in more than a century.

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"We were very focused on putting together a group of young position players, and he was the first piece of that," says Cubs general manager Jed Hoyer. "Anthony was the first guy we went out and got, and I guess it did start that movement toward having this really good young core of position players."

Jed Hoyer had been a believer in Anthony Rizzo ever since he drafted the first baseman in Boston. Photo by Jerry Lai-USA TODAY Sports.

The Cubs and the San Diego Padres ended the 2011 season with identical 71-91 records, and shared a fundamental problem: A dearth of young building blocks.

Chicago entered the offseason with only two under-30 players of note in its lineup: 28-year-old Geovanny Soto, coming off his second straight 17-home run season at catcher, and what seemed to be a franchise player in 21-year-old shortstop Starlin Castro. First base, meanwhile, was vacant.

San Diego, on the other hand, had one crown jewel on the major league roster—23-year-old starting pitcher Mat Latos, who had compiled a 3.47 ERA and 3.16 FIP over 194.1 innings the previous season. Rather than attempt to gradually construct a team around him, the Padres surveyed their organization and concluded that help was not on the way. On December 17th, Latos was sent to Cincinnati in exchange for a four-player package headlined by first baseman Yonder Alonso, the Reds' top prospect, who was blocked by the incumbent Joey Votto.


At the same time, the Cubs and Padres had another, far more significant thing in common. The Cubs, led by new team president Theo Epstein, had just hired Hoyer, the Padres' general manager, to fill the same position in Chicago. A source in the Padres organization at the time told VICE Sports that the move was precipitated by an internal power shift within San Diego.

Once in Chicago, Hoyer wasted little time circling back to his old club to inquire about one of his favorite former acquisitions. A year earlier, Hoyer traded for Rizzo as part of what would go down as the GM's signature move in San Diego, the five-player deal that sent Adrian Gonzalez to Hoyer's former employer, the Boston Red Sox—and, by extension, Epstein.

Rizzo was an Epstein favorite—"He was not a guy that Theo wanted to trade at all," Hoyer says—whose inclusion in the deal was mostly borne out of convenience. After all, between Gonzalez's arrival and David Ortiz remaining entrenched at DH, Rizzo would have no place to play. "The number of texts I got about him immediately after the trade from people still working for the Red Sox raving about makeup and 'This guy's not going to miss,'" Hoyer says. "That was kind of a no-brainer part of the deal for us, because we were losing Adrian, we needed a cheaper version of that."

Rizzo was promptly assigned to Triple-A and hit the ground running, beginning the 2011 season with 16 home runs and a .365/.444/.715 slash line. He was in the majors by June, with the San Diego Union-Tribune billing him as "the most celebrated Padres call-up since Roberto Alomar in 1988."


Then, he floundered. Rizzo struck out in 30 percent of his at-bats and hit .141/.281/.242. Less than two months later, he was back in the minors. When the season ended, Rizzo was 22 years old, with plenty of baseball ahead of him. His star had hardly faded, but Alonso's arrival gave San Diego a fresh, perhaps even more highly-regarded prospect to install at first base. More importantly, Byrnes, now officially Hoyer's successor as Padres general manager, believed Alonso's approach at the plate would translate far better to cavernous Petco Park than Rizzo's.

"At the time, Petco Park deflated home runs in right-center field and right field more than any other park," Byrnes told VICE Sports via email. "We were not yet discussing changing dimensions. We were about to better understand exit velocity and launch angle to get more insight into the effects of Petco. At the time, Rizzo's strengths were apparently going to get seriously dampened by the ballpark."

Rizzo was now in the very position Alonso had just been extricated from in Cincinnati: blocked with no foreseeable path to playing time on the major league roster. Meanwhile, with Latos off to Ohio, San Diego found itself in fresh need of young arms to build around.

Hoyer immediately recognized Byrnes' predicament. He still remembers where he was when he got wind of the Padres acquiring Alonso—in downtown Chicago, with his wife. "The first thing that pops in your head is 'Wow, Rizzo might be available," he says. "There's no way we get Anthony if that trade doesn't happen."


While Byrnes' faith in Rizzo may have been shaken, Hoyer and McLeod had no such concerns. Wrigley Field was much cozier than Petco. More importantly, "I also knew that the two biggest champions in San Diego were Jason McLeod and me," Hoyer says. "Being around a guy like Anthony, we realize how hard he's going to work to make himself successful. We believed in him in the draft in Boston. We believed in him going through cancer. Chemo, everything. We believed in him in San Diego and brought him up [at 21]."

And they believed in him despite that rough rookie year.

"He struggled for 140 at-bats, who cares?" Hoyer says. "We knew what went wrong and we kind of had the perspective of, 'So what, this guy's a really good player with good makeup. Let's just go get him.' And not over-thinking it based on what we saw."

Hoyer wasted little time getting in touch with Byrnes, anticipating plenty of competition to acquire Rizzo. But while Hoyer cites Toronto and Miami among the teams he heard were interested, Byrnes says that the sort of bidding war the Padres were hoping for never quite developed.

"There was not widespread interest or particularly aggressive interest in Rizzo," Byrnes says. "A first baseman really needs to hit to have value, and the market reaction demonstrated some hesitation."

Ultimately, it didn't matter, because Chicago had an asset that intrigued Byrnes: 25-year-old Andrew Cashner. A first-round pick out of TCU three years earlier, Casher stood 6-foot-6 and threw in excess of 97 miles per hour. At worst, San Diego figured he could be an impact reliever. At best, he could cushion the blow of trading Latos.


Like Rizzo, however, Cashner suffered through his own 2011 struggles. He was named Chicago's fifth starter out of spring training, only to strain his rotator cuff in his first start of the year. The injury kept him out until September, raising questions about the long-term stability of his shoulder. It may have made the difference between Chicago, a team thin on young pitching in its own right, making him off limits instead of agreeing to put him on the table.

"It was not easy for us to include him in this deal," Hoyer says. "We felt like we needed a little bit more stability if we were going to start this rebuild and Cashner missed the previous season. We knew he was super-talented but we felt like if we could get a little bit more certainty out of this piece, we should do it."

Brynes found himself weighing health versus performance. Ultimately, he opted to gamble on Cashner's ability at a position of need rather than keeping Rizzo and risking his value depreciating, either from sitting on the bench or languishing in Petco. "We understood the risk but were very intrigued by the upside," he says.

On January 6th, 2012, the trade was completed: Rizzo and starting pitcher Zach Cates to the Cubs in exchange for Cashner and outfielder Kyung-Min Na.

Josh Byrnes' acquisition of Yonder Alonso opened the door for a Rizzo trade to Chicago. Photo by Christopher Hanewinckel-USA TODAY Sports

Five years later, the results speak for themselves. Rizzo is a three-time All-Star, a Gold Glove winner and a franchise cornerstone on a World Series winner. Cashner has battled arm trouble and is now on his third team since the trade after inking a one-year contract with Texas this offseason.


"Usually those kinds of challenge trades don't happen," Hoyer says, and the reason why is above: they have the potential to make one team look especially foolish when they go badly.

It's hardly that simple, of course. As recently as 2013, the deal seemed to be tilting in San Diego's favor, after Cashner put up a 3.06 ERA over 26 starts while Rizzo hit just .233 on the season. Even in 2014, Rizzo's first All-Star season, Cashner's 2.55 ERA in an injury-shortened season provided encouragement that the deal seemed to work out for both sides.

"For two-plus years, he pitched like a mid-to-front-of-the-rotation type," Byrnes says. "Obviously, he has not been able to maintain that level of consistency."

As for Rizzo, Byrnes is quick to compliment his former player for achieving a level of success far beyond what he'd imagined. The power potential was unquestioned, but Rizzo's capacity to hit for average was an open question in San Diego. He answered it by raising his batting average by more than 50 points in 2014, and peaking at a career-best .292 in 2016.

"As much as any player I can remember, he totally changed his swing and approach after already reaching the major league-level," Byrnes says of Rizzo. "Credit to him for diagnosing a potential problem and finding a solution."

Still just 27, Rizzo is a figurehead within the Cubs organization and a superstar. He endured the franchise's lean years and was hardened by failure. Consequently, more than any other player on the roster, Rizzo has married his considerable youth and abilities to clubhouse clout.

"It helped him as a leader, having to go through that," Hoyer says. "I love the fact that he has perspective on 101 losses, perspective on 96 losses and he was here when we were struggling. Some of these other guys, they came up and we were good by that point, so they didn't have to live through those years."

Perhaps it was fitting, then, that success didn't come as swiftly to him as it did Bryant, Schwarber, Russell and Contreras, the other young stars of this year's World Series winner. Then again, it's not like it came slowly.

"By 24, he was an All-Star," Hoyer says. "That's a pretty fast ascent when you remember he came up so early. It wasn't like he took so much time. He took some time."

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