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.

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Jeff Samardzija/Jason Hammel for Addison Russell, Dan Straily, and Billy McKinney

One of the best young shortstops in baseball, many were floored when they saw what the Cubs got in return for Jeff Samardzija and Jason Hammel. That would be Addison Russell, who, at the time, was deemed “untouchable,” and for good reason. Russell was top shortstop prospect, with comparisons to Barry Larkin, and was a top five prospect in baseball.

Russell has been so good defensively, and shown flashes of superstardom offensively, he will be manning short at Wrigley for, what fans hope, is many years. Not to mention, the Cubs managed to resign Jason Hammel in the ensuing offseason.

Russell has a few gold gloves in his future, and most fans can agree to that, just seeing him play. He was clumped in with the Carlos Correa/Francisco Lindor/Xander Bogaerts/Corey Seager crop of shortstops. The kid’s got talent.

Russell has shown flashes of just how good of an all-around player he can be. He can hit the ball a long way when he gets into one, he has a fantastic eye, great base runner, just an all around good player. The scary thing with Russell is that there is so much more room for improvement.

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That’s not a knock on him, that’s just how talented he is. If the Arrieta/Strop trade was a coup, imagine what this trade could end up being down the road. Since being called up last year, Russell has hit at a .244/.319/.398 clip. Now, that certainly isn’t anything to write home about. It’s the strides he’s made in 2016 that have Cubs’ fans licking their chops.

He’s already passed last season’s RBI total, he could push 20 homers, and, the main area where Russell has struggled at the plate, is hitting lefties, as the year has gone on, he has gotten better and better. Keep in mind, he’s 22. Russell is mature beyond his years and has many more great seasons to come.