Theo Epstein Back in the Bronx with Rebuilding Cubs

The last time the Yankees and Cubs met was August 2011, but that was at Wrigley Field. On Tuesday, the Yankees and Cubs meet for the first time ever in new Yankee Stadium (since their Stadium opening exhibition games didn’t count) for a two-game series, which will be the first of a pair of two-game series this season between the teams.

With the Yankees and Cubs playing for the first time in three years and the first time this year, I did an email exchange with Al Yellon of Bleed Cubbie Blue to talk about what has happened to the Cubs since their last postseason appearance in 2008, the job Theo Epstein has done since taking over before the 2012 season and how long Cubs fans expect the rebuilding process in Chicago to take.

Keefe: I have never been to Wrigley Field though I expect that to change this summer. I went by it for the first time in January when I was in Chicago for Rangers-Blackhawks and tried to envision what it would be like to watch a game inside there and soon enough I will have that chance. It’s hard not to think of the heartache and the devastation that has taken place there and for the teams that have played there and the fans that have watched games there. And the most recent of that heartache and devastating came five-plus years ago.

The last time the Cubs were in the playoffs in 2008, many people predicted them to go to the World Series and even win it all after winning 97 games in the regular season. But then they ran into the wild-card Dodgers and three games later, the Cubs’ season was over. A year after getting swept by the Diamondbacks, they were swept by the Dodgers and they haven’t been back to the playoffs since.

I know it’s not exactly the most positive note to start his email exchange by bringing up the Cubs’ postseason failures of 2007 and 2008 or their playoff drought since, but I thought it was a good place to start to set the tone of where your Cubs have been recently and where they are doing.

Going into the 2008 postseason, how confident were you as a Cubs fan (I’m guessing as confident as a Cubs fan can be) coming off that regular season? Did you think the team was built to make annual October appearances or was there a sense of what would eventually come?

Yellon: This is a question few Cubs fans care to revisit. More than five years gone, it feels as if 2008 was another lifetime. Ownership and management have completely changed since then, and it’s almost as if we’re now rooting for an expansion team.

Oh, 2008. Best regular season I’ve seen in my lifetime, probably the best Cubs regular season since the 1930s. No Cubs fan anticipated a three-game sweep. 20/20 hindsight says that team was built to “win now,” in the vernacular, because it made the playoffs mostly on the strength of veteran hitting.

Cubs fans didn’t look toward “annual October appearances” at that time. We took what came and felt grateful for it — in some ways, always anticipating something going wrong. There’s an old joke: Optimists think the glass is half full. Pessimists think the glass is half empty. Cubs fans ask, “When’s the glass going to get knocked over and spill?”

Keefe: I have always felt that Theo Epstein got too much credit in Boston. Yes, he pulled off a miracle during Thanksgiving dinner in 2003 at Curt Schilling’s house to get the right-hander to sign with the Red Sox and he had the balls to trade the face of the franchise in Nomar Garciaparra in the middle of the 2004 season. But he also won the 2004 World Series thanks to a team whose key players were from prior management. And then when the Red Sox won again in 2007, it was because Josh Beckett saved them in the ALCS and because of Mike Lowell in the World Series, as he won MVP against the Rockies. Those two players were traded to the Red Sox from the Marlins during Epstein’s time away from the team, and he admitted then he wouldn’t have made that deal. No deal, no World Series that year.

I loved what Theo did by signing bad deal after bad deal to put the Red Sox in a bind through the 2012 season before he left Boston for Chicago and before Ben Cherington cleaned up his mess. But I couldn’t believe how ecstatic Cubs fans seemed to be with the news he was headed for Wrigley as if they had just landed A-Rod in a pre-2004 trade.

What were your feelings about the decisions to bring Theo to Chicago?

Yellon At the time Theo was hired, I was all for it. It was clear the team’s direction wasn’t working and they needed a change.

In the two-plus years (three offseasons, now) that Theo & Co. have been in charge, they have produced what is seen by many analysts as the top farm system in the major leagues, stockpiling draft picks and acquiring prospects by trade.

Many think this is great, and that the Cubs will magically burst into contention starting in 2015 with prospects such as Javier Baez, Kris Bryant, Albert Almora and Jorge Soler (known as the “Core Four”). In general, it doesn’t work that way; those four might become All-Stars, but it could take time. It could be 2018 or later before the Cubs return to contention; they are hamstrung by poor TV deals and some other financial constraints put on the team as a condition of the sale to the Ricketts family, that might not get them the big money they need to compete with the likes of the Dodgers and Yankees until after 2019.

Some Cubs fans are OK with this, thinking that the “waves of talent” Theo is supposedly producing will provide perennial contention. Others are starting to get a bit impatient with the 95-plus loss seasons that are piling up; 2014 is likely going to be another such season.

Keefe: There aren’t many non-Yankees I like, but I like Starlin Castro. Now I don’t watch him every day like you, and I haven’t followed his career as closely as you, but his first few seasons are puzzling when you look just at the stats.

The last time the Yankees and Cubs played (and the only time Castro has played against the Yankees) was June 17-19, 2011. In those three games, Castro went 5-for-13 with two doubles and three runs, but it felt like he couldn’t be stopped. He went on to hit .307/.341/.432 and led the league in hits that year in what was his second season. But since then, his average, on-base percentage and slugging percentage have declined each season. However, early on this year, Castro looks to be back on track and he just turned 24 on March 24.

I know he’s still very young, but what has kept Castro from building off his 2010 and 2011 seasons over the last two years?

Yellon: To be quite blunt, Castro’s struggles can almost completely be attributed to the manager and coaching staff that was dismissed at the end of 2013. Dale Sveum (a former hitting coach) and his staff had Castro change his approach. Castro came to the big leagues as (mostly) a hacker — note the .341 OBP with the .307 BA, not many walks in there — and Castro got all messed up, trying to please the coaches, taking too many pitches and not getting good swings at the pitches he did offer at.

There were also some personal issues in his life (a sexual assault charge that proved baseless, among other things) that could have affected his play on the field.

New manager Rick Renteria and batting coach Bill Mueller have let Castro be Castro, to go back to the style that got him to the big leagues and have two All-Star seasons. He’s done quite well so far in 2014 despite missing almost all of spring training with a hamstring injury. He looks more confident at the plate and has also played better in the field (it’s always been noted that Castro has had some issues with concentration in the field, but this appears to no longer be a problem).

As you note, he’s just 24. He’s had very good years in the past and now it looks like he could be in line for a real breakout year.

Keefe: It was always rough to watch Carlos Marmol try to get through games as the Cubs closer (especially if you had a wager on them), but when he was on and could locate, his pitches were electrifying and unhittable. Now it seems like the Cubs have Carlos Marmol 2.0 in Jose Veras.

I couldn’t wait for the Yankees to part ways with Jose Veras, which they did in June 2009, and had they not, the Yankees probably would be in their 14th year of a World Series drought if he had gotten into playoff games that year. Veras defined inconsistent during his time with the Yankees and when I knew he would be an important part of the Tigers’ bullpen in the ALCS last October, I feared that the Red Sox would reach the World Series and eventually win it.

The numbers haven’t been pretty for Veras through four appearances this season, so I’m not sure if the right thing to ask is what are your feelings on him, so I’ll go with how long will the Jose Veras experiment work with the Cubs?

Yellon: I think the Veras experiment might be over already; he’s been replaced as closer (for now), and if his replacement (whoever it is; the dreaded “committee” is now closing) does well, what’s the point of giving him the closing job back?

Well, here’s the point. Veras was signed as a flip candidate; he has very little “proven closer” experience (half of 2013 is about it), and there isn’t much point to having a 33-year-old closer on a bad team unless he can bring a prospect or two in return. So I’d expect the Cubs to try it again.

Keefe: The year before Theo arrived the Cubs were 71-91. In his first year running the team, they finished 61-101 and then went 66-96 last season. This year they are off to a 4-8 start.

They are still considered to be in rebuilding mode, but when you look around the league at other teams who were also rebuilding, they have seemed to do it much quicker than it’s taken the Cubs, who haven’t reached the playoffs since 2008 and haven’t won a playoff game since Game 4 of the 2003 NLCS.

What are your expectations for this season and how long will the rebuilding plan take?

Yellon: Personally, I have no expectations for this season. This Cubs team was clearly not built to contend, especially in the NL Central where it appears we now have four contending teams. The Cubs’ two “big” offseason signings — Veras and Jason Hammel — were clearly made to flip them for prospects, not to provide any victories. The Cubs will likely lose 95 games again, even if they play well through July 31; trades after that (which could include Jeff Samardzija) could produce another 18-42 or 17-40 August and September (those are the actual records from those months in 2012 and 2013, respectively).

I don’t expect the Cubs to have any real serious contending year until 2018… at least.

But hey, we’re celebrating the 100th anniversary of Wrigley Field this year. There will be some cool giveaways. As Cubs fans, we better enjoy that, because it’s about all we’ve got.

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