Chicago Cubs: Best deadline trades during the Theo Epstein regime

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The Chicago Cubs’ Theo Epstein has been on both ends of the deadline. Previously as sellers, and now as buyers. But each deadline deal had importance to the Cubs in some form. We look at the deadline moves he’s made over the past six years.

There have been trades that have happened outside of the deadline, but those won’t count here. We’re looking at the Chicago Cubs moves at the trade deadline (and a little before) to see just how important the moves that Theo Epstein & Co. made were. Whether looking to the future or going all in now, Epstein has done an excellent job of putting the team in fantastic position to succeed.

had shown will take us back to the beginning–or “the before time”–of Cubs baseball. Epstein inherited a team that was less than impressive on the field, and even worse on the team’s checkbook. So Epstein went to work each deadline to change the focus of this Cubs team. From “lovable losers” to a borderline dynasty, Epstein has hit on more than he’s missed with the deadline deals he’s made.

Let’s take a look at what he’s done in his time in Chicago, and why this might only be the beginning of this list.

Doing the minimum

In 2015, the Cubs weren’t exactly tearing it up heading into the deadline. But the play had improved, and Epstein decided that pitching was where they needed the help. So the Cubs made a move to trade Junior Lake to the Baltimore Orioles for reliever Tommy Hunter. Lake had fallen out of favor after a solid rookie year in 2013 (.284, 6 HR, 16 RBI). He was never able to find the stroke he had in ’13, and the Cubs decided they could do without him.

In Hunter, the Cubs got a pitcher that had saved a few games the year before (11 of 17) but looked to fit in the middle of the pen. Unfortunately, Hunter wasn’t the same pitcher that he was for the O’s. After posting a 3.63 in 39 appearances with Baltimore, he struggled with the Cubs. In 15 2/3 innings, he allowed four home runs (only three in Baltimore) to the tune of a 5.74 ERA. Hunter wouldn’t make the playoff roster as the Cubs would lose to the New York Mets in the NLCS.

(Photo by Michael Thomas/Getty Images) /

“ithrow88”

There may not have been a more entertaining guy than Dan Haren. Able to poke fun at himself for his inability to throw hard, the Cubs offered a “swan song” of sorts for him to finish out his career. After missing out on David Price and Cole Hamels, the Cubs settled on the Haren to fill the gap.

Haren did finish 4-2 with the Cubs, but it wasn’t an impressive effort with Chicago. Often, Joe Maddon wouldn’t stick with Haren long, as he went less than five innings in four of his 11 starts. Just like Hunter, Haren was left off of the playoff roster as the Cubs went with what they had.

Haren called it a career after his time in Chicago, finishing his career with 153 wins. Haren was also a three-time All-Star, once with Oakland and twice with the Diamondbacks.

(Photo by Jonathan Daniel/Getty Images) /

Cubs capitalize on Bonifacio

In 2014, the Cubs signed Emilio Bonifacio hoping he could hold things together during the rebuild. And then he became part of it. After having a solid first half, the Cubs packaged him up with reliever James Russell and sent them to Atlanta. In return, they got a young catcher by the name of Victor Caratini.

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Caratini just recently made his debut and hit a game-winning home run against the Milwaukee Brewers. The move might be short lived as with the addition of Alex Avila, Caratini might quiet down to Triple-A Iowa. But he’s gained some valuable experience in his time in Chicago, and we may see him again soon when the Cubs make their September call-ups.

The Cubs saw the writing on the wall with Russell and chose to part ways with him. He would return to the Cubs in 2015 for 49 games (0-2, 5.29 ERA), but that would be it for his time in Chicago. Russell last pitched for the Phillies in 2016.

Getting some of it back

Most Cubs’ fans know what the team gave up to get Matt Garza. If you don’t, you can go here to see. But in 2013, the Cubs did their best to recoup some of their investment back. By dealing Garza, the Cubs received some talented but unproven prospects. The Cubs got a skinny Carl Edwards, as well as Mike Olt and Justin Grimm. I think most of the hope was in Grimm and Olt, with Edwards “thrown in”. Well, that was wrong.

Olt showed his power, but a propensity to strike out came with it. It turns out that the “string bean slinger” doesn’t like to be doubted. Edwards has worked his way through the system and has become a critical part of the Cubs bullpen. Grimm has had his ups and downs this year, but he played his part in helping the Cubs win the World Series last year.

Who knew?

If there’s one thing that Epstein wasn’t afraid to do, it was trading the favorites. Ryan Dempster was nearing the end of his career but was still a formidable pitcher. He had a minuscule ERA (2.25), but the Cubs simply weren’t helping him any. Then, Epstein got on the phone and called the Rangers. It turned out to be a good move.

The Cubs got Kyle Hendricks and third baseman, Christian Villanueva. Villanueva was one that Cubs’ fans thought might be one of the next stars after a couple of good years in the minors. But he never panned out and is now in the San Diego Padres system.

But the unassuming kid in Hendricks turned out to be more than the Cubs could have imagined. After his first two seasons showed promise, Hendricks had a breakout year in 2016. His 2.13 ERA led the NL as he won ERA title, as well as finishing third in CY Young voting. After missing some time due to injury, Hendricks hopes to be part of a Cubs’ return to the World Series.

Part of the rotation for the future of the infield

The Cubs had hoped to sign Jeff Samardzija to a long-term extension, but he laughed at the Cubs. He mocked the “wait till next year” approach. How’s that looking, Jeff? Once the Cubs realized that Billy Beane was willing to part with Addison Russell, they went for it. It took two-third of their rotation in Samardzija and Jason Hammel, but the deal was done.

For Starlin Castro, this signaled the end for him in Chicago–he just didn’t know it yet. With Russell making his way through–and eventually unseating Castro at short–time was ticking for Castro. In 2015, he played his final season with the Cubs before being traded to the Yankees. Ben Zobrist came over and that all but nailed the coffin shut on his time in Chicago. But Russell has had his issues–on the field and off–but is looking to be the clutch player they could count on last season.

A worthwhile rental

It was one of the only “weak” spots the Cubs felt they had. Hector Rondon was a good closer, but not a “lockdown” closer. Aroldis Chapman was that guy, and the cost to get him into a Cubs uniform for a half of a season wouldn’t be cheap. As far as the Cubs were concerned, the cost would be worth its weight in gold.

The Cubs gave up their top prospect in Gleyber Torres, as well as sending Adam Warren back to New York. They also sent Billy McKinney and Rashad Crawford as well. It was a 4-for-1 deal, and a rental, at that. Did the Cubs give up too much?

A World Series title–the first in 108 years–should answer that. There may come a time when we’ll look at the Cubs and Yankees trade as feel that the Yankees got the best of it. And that’s fine. The deal ended the 108-year drought, no matter how you might look at it.

Going for it again

When the Cubs went and got Jose Quintana from the White Sox, it wasn’t necessarily a “go for it” move. The Cubs are very likely to lose John Lackey and Jake Arrieta, so this move made sense. While it came at a high cost, including the top two prospects in the Cubs’ system in Eloy Jimenez and Dylan Cease–it was one they felt they needed to make. The Cubs added two other prospects in the deal, making it another 4-for-1 deal, but a much better one this time around.

Once the Cubs got off to–and continued–the hot start in the second half, Epstein decided this was as close to a dynasty as he might get. The Cubs got the pieces that were looking for in backup catcher Alex Avila and reliever Justin Wilson. Avila will be nothing more than a rental, but Wilson is arbitration eligible next season. So the Cubs get a valuable addition to the pen for next season. And, if Wade Davis chooses to sign elsewhere after this offseason, the Cubs will have Wilson and Rondon to close games.

Next: Bartman gets a ring

Epstein has shown faith in this team but being a buyer and not a seller–not that we ever thought that would be the case. Not we just have to wait and see what kind of magic this team has in store for us. With all of the deadline deals that took place today, the rest of this season should be exciting.

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