Cubs: Ranking the five best moves during the Theo Epstein era

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Theo Epstein transformed the Cubs in countless ways. Here are his 5 best moves.

As we close the book on Theo Epstein’s tenure in Chicago tomorrow, there are a lot of emotions. We’re talking about the architect who not only delivered the Cubs‘ first World Series title in over a century, but completely transformed the organization – and the expectations surrounding it on a year-to-year basis.

Over the last nine years, the three-time World Series champion executive has made too many moves to count. Granted, they weren’t all home runs (remember Edwin Jackson?) – but he pulled the right levers and pressed the right buttons to propel the Cubs to three division titles, a trio of NLCS appearances and a World Series championship. Not too shabby in the grand scheme of things.

Rather than focus on specifically trades or only free agent signings, I decided to go with the top five moves Epstein made while at the helm in Chicago. The order is completely of my own choosing. You could definitely make the case for your own, but I think at the end of the day, these five moves had the most lasting impact on the franchise.

Cubs: Theo Epstein’s Greatest Moves: No. 5 – Signing Ben Zobrist

Coming off a World Series title with the Kansas City Royals, switch-hitting utilityman Ben Zobrist was a hot commodity heading into the 2015-16 offseason. Epstein swooped in and locked him up on a four-year, $56 million deal. This, of course, proved critical in the years to come.

During the team’s World Series campaign, Zobrist earned the third All-Star nod of his career, slashing .272/.386/.446 after being reunited with Maddon, his former manager in Tampa Bay. His versatility was critical to keeping key guys fresh, not only in 2016, but during his four years on the North Side.

His biggest moment came in Game 7 of the Fall Classic, when he punched a go-ahead RBI double down the third-base line in the tenth inning, which put the Cubs ahead for good. No one will ever forget him jumping into the air upon reaching second base as his teammates went wild in the dugout.

Zobrist’s contributions in the World Series went far beyond that knock, evidenced by his .919 OPS over the seven games. He earned World Series MVP honors – and although his Cubs career ended in a rather unceremonious fashion, he was a critical piece to the team’s run in the back half of the decade.

(Photo by Jonathan Daniel/Getty Images) /

Cubs: Theo Epstein’s Greatest Moves: No. 4 – Bringing in Joe Maddon

After the Chicago White Sox dumped Ricky Renteria after he led the team to the postseason this year, you have to feel bad for the guy. Why? He bore the brunt of the rebuild on the other side of the city – only to have Theo Epstein fire him so he could bring in longtime Tampa Bay skipper Joe Maddon.

The move paid off immediately, with Chicago making an unanticipated run to the NLCS in 2015 on the heels of a 97-win regular season. The eccentric skipper won NL Manager of the Year, Kris Bryant earned Rookie of the Year honors and Jake Arrieta cruised to the NL Cy Young Award.

Of course, the Maddon-led Cubs followed that up by winning it all the next year, with Bryant winning NL MVP and Kyle Hendricks and Jon Lester earning two of the three NL Cy Young finalist spots. Those two years were remarkable on the North Side of Chicago.

Maddon led the Cubs back to the NLCS for a third consecutive year in 2017, but the team was running on fumes. While 2018 and 2019 paled in comparison, the three-time Manager of the Year left an indelible mark on the franchise – and will forever hold a spot in the hearts of all who witnessed this Golden Era.

(Photo by Justin K. Aller/Getty Images) /

Cubs: Theo Epstein’s Greatest Moves: No. 3 – The Jake Arrieta-Pedro Strop trade

When we’re talking about my all-time favorite Cubs, the final two comes down to Hall of Famer Ron Santo and none other than Jake Arrieta. His jawing at Pirates fans on Twitter ahead of the 2015 NL Wild Card Game was next-level; and the fact that he backed it up is the stuff of legend.

Arrieta came to the Cubs along with right-hander Pedro Strop in a 2013 trade with the Baltimore Orioles. This trade ranks as one of the most lopsided in baseball history. Arrieta went on to win a Cy Young Award with Chicago, backed up by a 2.73 ERA in 128 starts. In the 2016 World Series, he did everything in his power to shoulder the burden, striking out 15 in 11 1/3 innings of work.

I could go on about Arrieta for days. But that wouldn’t do Pedro Strop the service he deserves. Love him or hate him (if you dislike him because he wears his hat angled, I don’t care about your opinion) – but the guy was a huge part of the Cubs’ success. Numbers don’t lie.

From 2014 to 2018, Strop averaged 65 appearances annually, working to a 2.61 ERA, 1.029 WHIP and 10.1 K/9 mark. His wipeout slider paired perfectly with his fastball and he was Maddon’s go-to guy in tight spots for much of this time. And to think – Epstein landed both of these guys for the likes of Steve Clevenger and Scott Feldman.

(Photo by Brian D. Kersey/Getty Images) /

Cubs: Theo Epstein’s Greatest Moves: No. 2 – Trading for Anthony Rizzo

Oh captain, my captain. Anthony Rizzo is the undisputed face of the Chicago Cubs franchise. Since coming over ahead of the 2012 campaign, there’s little he hasn’t done on – and off – the field.

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Rizzo is a three-time All-Star, four-time Gold Glove recipient, a Platinum Glove honoree and a Silver Slugger winner. Not to mention he’s a World Series champion and has performed like clockwork over the better part of a decade.

Since 2014, Rizzo has essentially averaged 30 home runs and 100 RBI with a .284/.388/.513 slash line, while providing stellar defense at first base. He’s the heart and soul of this team and I’d imagine we see a statue of the slugger outside the Friendly Confines someday for all his efforts.

Epstein was uniquely familiar with Rizzo. After all, the Red Sox – under Epstein – drafted him back in the sixth round of the 2007 draft. New president of baseball operations Jed Hoyer knew Rizzo from both Boston and San Diego. After picking up his option for 2021, we all have to wonder – is this the swan song for Rizzo at the Friendly Confines?

Cubs: Theo Epstein’s Greatest Moves: No. 1 – Signing Jon Lester

Theo Epstein had to sell Jon Lester on what he was building in Chicago. His pitch to the coveted left-hander included a presentation of him on the mound with a Cubs’ World Series title at stake. Less than two years later, that came to fruition with Lester coming out of the pen in Game 7 in Cleveland.

While his win-loss record in 2015 wasn’t what you’d like, he proved that’s not how you measure success with pitchers. He worked to a 2.92 FIP across 205 innings, cementing himself atop the rotation. He followed that up with a runner-up finish in the NL Cy Young voting in 2016 – adding a third World Series ring to his collection.

Although he’s certainly not the pitcher he was back at the start of his Cubs tenure, Lester has continued to reinvent himself on the bump. There are few better big-game pitchers in baseball today and, when October comes around, he’s the guy you want to have the ball.

Next. Ranking the all-time greatest Cubs players. dark

Over 1,000 innings of regular season action, a pristine postseason resume, two All-Star appearances and a World Series title. The Cubs got exactly what they were hoping for in Lester – and it’s clear he’s not just the best move Theo Epstein made here, but one of the all-time best free agent signings in Chicago sports history.

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