Chicago Cubs: Theo Epstein’s made few mistakes in Chicago

When the Chicago Cubs hired Theo Epstein to oversee the “rebuild”, it’s highly unlikely they saw it going as smoothly as it has. But it doesn’t mean there weren’t a few “missteps” along the way.

You have to wonder when it was that Chicago Cubs‘ owner Tom Ricketts decided Theo Epstein would be the man for the job. After watching him break the “Curse of the Bambino” when did Rickett’s start thinking about breaking the curse of that damn billy goat? Whenever he first thought about it, it was October 12, 2011, that they made it happen.

The Cubs, unlike the Boston Red Sox when he took them over, were not a winning team. And things got worse before they got better. But that was exactly what Epstein preached. Trust the plan. Five years later the Cubs raised their first World Series trophy since 1908. Two of the longest droughts in baseball history had been ended by one man.

I’d love to say that it was smooth, but we all know that wasn’t the case. What doesn’t kill you makes you stronger, or so the saying goes. In the end, all of these were things that Epstein hopefully was able to learn from. So we give to you five of Epstein’s “poor” choices–but all outweighed by the good ones.

Cubs trade LeMahieu, Colvin to Rockies for Stewart, Weathers

I’ll be the first to admit that what hurt me about this trade was losing Tyler Colvin. After surprising everyone and making the Opening Day roster with a strong spring, Colvin did well in his rookie campaign. But things came crashing down for him in September when he was hit with a broken bat as he was running, ending his season. After a 20 home run season, Colvin never seems to find his way again at the plate.

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DJ LeMahieu was a scrappy infielder that many didn’t see as having a promising path to the majors. Whoever came up with that scouting report can set that on fire. This is one of the many downfalls of trading prospects. You just can’t know how they’ll develop. At the time, there was nowhere for LeMahieu to play on the Cubs infield (generally speaking). It was Blake DeWitt who had that job. I know, I had forgotten about him, too. Since 2014, LeMahieu is a Gold Glove winner, and All-Star and an NL batting champ. But clearly, the deal worked out for the Cubs, right? Nope.

In return, the Cubs acquired third baseman, Ian Stewart. Stewart was a player that struck out a great deal (27.9% K-rate at that time), but showed potential power. He came off of a dreadful 2011 season in which he hit .156 and failed to homer even once. But the Cubs saw his 53 home runs in the previous three seasons as a reason to take a shot at Stewart. The Cubs would release Stewart in June after a horrendous stint in Chicago. At least Epstein had the good sense to part ways with Stewart when he did.

 Cubs sign Jackson to four-year, $52 million deal

This one falls as one of the more difficult ones to swallow in the Epstein era. If you look at the Baseball-Reference page of Edwin Jackson, it’s a long list of teams and jersey numbers. Jackson had never shown enough to convince any other team to sign him to a long-term deal. But the Cubs turned out to be the ones to fall for it.

The thought was that Jackson could be an innings-eater, helping to anchor the staff. Jackson had been around or over 200 innings pitched each year since 2008, so that plan made sense. The team also thought that as they improved, Jackson would be there to assume his place near the top of the rotation as they “turned the corner”.  He turned out to be none of those things, except very, very costly.

In his first two seasons, Jackson went 14-33 with a 5.58 ERA. I see no reason to go into deeper metrics because none of those are any better. Jackson was horrible. But unlike Stewart, the Cubs didn’t seem to know what to do with him. And unfortunately, losing 33 games in two seasons doesn’t attract a lot of suitors for a trade.

In 2015, Jackson was moved to the bullpen and seemed to have gotten back on track. In 31 innings pitched he posted a 3.19 ERA with the Cubs. But that July Epstein finally pulled the plug on the E-Jax experiment, releasing him. The Braves picked him up–on the Cubs tab, mind you–and pitched well for them the rest of that season. He’s had a stint with the Marlins and the Padres but is currently a free agent this winter.

Cubs sign Veras as closer to a one-year, $3.85 million +$150k buyout

The Cubs were slowly turning the corner and the signing of Jose Veras was an upgrade over Kevin Gregg from the year before. Yes, Gregg turned out to be one of the “better” pickups for Epstein, and his replacement one of the worst. But it was apparent in Spring Training that Veras didn’t have that closer mentality he showed in Houston. It only got worse once the games counted.

It took less than 10 days for Veras to lose his job as closer. Walks and home runs plagued him. In 13 1/3 innings, he posted an 8.10 ERA with 12 ER and 11 walks. A trip to the DL with an oblique strain was likely just to buy time for the Cubs to try and figure a way out of this mess. But it was clear, there wasn’t one. Veras was DFA’d on June 3 and the damage was done. The Cubs would owe him the remainder of his contract PLUS his $150k buyout.

Cubs trade Torres, McKinney, Crawford and Warren to Yankees for Chapman

This is a deal that right now, without a doubt, is worth it. But there’s no doubt the Cubs gave up a player with a high ceiling in Gleyber Torres. Anyone that has had the opportunity to see him play knows that. Along with Torres, the Cubs sent back Warren as well as Rashad Crawford and Billy McKinney. Will we look back at this deal in a few years as a “bad move”?

But remember this, everyone wants to see a dynasty–until it happens. Then they want to see it torn down.

Regardless, this was a move that the Cubs made knowing what they were giving up–and what it could potentially bring to Chicago–a championship. Aroldis Chapman was the closer the Cubs needed. Yes, they rode him hard down the stretch. But when you’re fighting for your first World Series in 108 years, everyone has to bare down and make it happen. Chapman may have given up the game-tying home run to Rajai Davis. But don’t forget when he came out the next inning and held the Cleveland Indian scoreless, giving the Cubs another chance. It was a gutty performance, indeed.

As of now, Torres didn’t have a place in the Cubs infield. Which is a similar story to that of LaMahieu. In this case, the Cubs have a World Series to show for this trade. Not Ian Stewart. But this could be one where the Cubs are watching the young Torres shine for the Yankees for many years to come. As long as I don’t ever have to see Torres hit a game-winner against the Cubs in the World Series? I’ll be okay with this one, no matter how much it might sting.

Or so the saying goes…

Epstein has hit the mark WAY more often than he’s missed. Brian Cashman and the Yankees may have won this most recent deal. But it was Epstein that parlayed players like Jeff Samardzija, Scott Feldman and Paul Maholm into a strong roster that won a World Series. We trusted the process, the plan–and it paid off.

The first five years of the Epstein era were indeed successful and leaves all of us with high hopes of what comes next. Could we be talking about a possible dynasty? Maybe. But remember this, everyone wants to see a dynasty–until it happens. Then they want to see it torn down. The transition from “Lovable Losers” to dynasty will be non-existent. Do we have any issues with that? No, I didn’t think so.