Chicago Cubs: What’s been Theo Epstein’s best trade?

It’s been a successful five-year tenure in Chicago for Theo Epstein and his crew. Epstein has made many trades, and many of these trades have helped shape the team into what it is today.

We know about the trades for Miguel Montero, Dexter Fowler, and Justin Grimm. Grimm and Carl Edwards, Jr. were both acquired together for Matt Garza. Let us not forget about the trade for Kyle Hendricks, coming over from the Rangers for Ryan Dempster, in 2013.

Or this year, when they acquired a young, cost-controlled arm in Mike Montgomery, who can be a swing man between the bullpen, and the rotation.

Montgomery has experience doing both, as he was a starter in the minor leagues for the Royals and the Rays. Once the Mariners acquired him, they turned him into a reliever, and it’s worked well.

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The thing about rebuilds is that they take a little bit of everything, meaning good drafting, making good acquisitions in free agency, and making trades that acquire young, impactful players, all to build up a strong farm system, where the young players can develop until they are ready for the big leagues.

The Cubs have done that very thing. Not to mention, they’re farm system is still very strong to this day. They are still looking to make trades before this year’s August 1st trade deadline, mostly for young, cost-controlled pitching. Jayson Stark mentioned a possible match with the Rays.

With newly acquire Aroldis Chapman joining the team, it’s time to sit down and examine which trades have been Epstein’s best, most impactful trades?

Next: Cubs find their ace, bullpen horse

Scott Feldman and Steve Clevenger for Jake Arrieta and Pedro Strop

This one is a no-brainer. The Chicago Cubs took a chance and found an ace, as well as a bullpen anchor. Strop has worked out of numerous big spots during his tenure, and Arrieta has become nothing short of dominant. They turned a one year deal from a mediocre pitcher into a dominant ace and great setup man.

Arrieta didn’t come without questions, though. With Baltimore, Arrieta averaged nearly four BB/9 and had an ERA of well over five. Since joining the Cubs, he’s lowered his ERA by nearly three runs, his walk rate is down to just 1.3 BB/9.

Arrieta has transformed himself into one of the best pitchers in baseball. He’s added a Cy Young to his resume as well. Arrieta is a guy that Cubs fans would love to see signed to an extension after 2017.

As for Strop, he has become stable in the back-end of the bullpen for the Cubs. Not only has Strop established himself as one of the most dominant relievers in the National League, he’s settled into that 8th inning, setup role, setting it up for Hector Rondon in the 9th. However, now Strop may have to settle into the 7th inning, and Rondon may set it up for the newly acquired closer, Aroldis Chapman.

Since joining the Cubs, Strop has never had an ERA greater than three. To put that into a little perspective, his career ERA is 3.25, which speaks to how much he struggled before coming over to the Cubs. His Batting average against with the Cubs has never been above .200.

It’s remarkable that Strop has maintained his consistency for as long as he has. This trade really helped the Cubs take that next step during the rebuild. Strop is a free agent after this year, and the Cubs should really look at working out a new deal to bring him back.

Next: It all begin with Rizzomania

Andrew Cashner for Anthony Rizzo

Hard to believe, but this has become sort of forgotten trade in the Epstein tenure, mainly because it was his first trade that he made, five years ago. What a steal it has become. Rizzo has turned into a perennial All-Star and MVP candidate, while Cashner can’t seem to shake the injury bug. Rizzo has a history with this front office, dating all the way back to the Red Sox, as Epstein and general manager Jed Hoyer originally drafted him.

Hoyer then acquired him in San Diego, intending for him to be a franchise cornerstone. Rizzo has followed them to Chicago, where he was intended to be the forefront of the rebuild, and he’s followed through, becoming the franchise cornerstone he was always intended him to be. Before becoming the superstar he is, though, it was a rough road for Anthony.

He was diagnosed with Leukemia in 2008, right when he had just started playing professional baseball. Rizzo overcame it and has worked hard to get where he’s currently at. Off the field, he runs the Anthony Rizzo Family Foundation, which helps families battling cancer. What an easy guy to root for.

Not only has Rizzo turned himself into an All-Star and MVP Candidate offensively, he plays Gold Glove defense at first base, yet the Gold Glove continues to elude him. His time in San Diego was…not memorable. He was first called up to the Padres in 2011, where he played in 49 games, and hit just .141, with one home run.

Once the trade to Chicago happened, he took off and has found a home. He’s signed to a long-term, team-friendly contract through 2019, with two options for 2020-2021. Rizzo is the face of the Cubs’ franchise and looks to be around for years to come, as does the next person on our list.

Next: Giving up arms for future All-Star shortstop