For Cubs Pursuit of Players, Sometimes It's Better to Swing and Miss

For Cubs Pursuit of Players, Sometimes It's Better to Swing and Miss

The Cubs have made some mistakes in recent years but they also have luckily missed on players they have been connected to. Every once in a while, you see a player swing at a perfectly good offering, only to flail and look helpless at the plate; To quote Weezer: "Here's the pitch, slow and straight. All I have to do is swing and I'm a hero, but I'm a zero." Other times, he'll just miss squaring up a pitch, maybe fouling it straight back or just outside one foul pole are the other.

And then there are those pitches that the discerning batter lets go, the "pitcher's pitchers" that are called strikes but that can't be put in play with any good results. It sure feels like the Cubs have had more than their share of the first two examples, but they've taken some pitches that many would've rather had them swing at.

Here is a look at players the Cubs were connected to/traded for/missed on that would have made things a lot different for the Cubs moving forward.

Total Whiffs

Nomar Garciaparra

This one is so unfortunate. Was there a player the Cubs signed or traded for that people in Chicago got more excited for than when Hendry traded for Nomar?  Maybe Soriano? Back in the day there were three shortstops everyone talked about: A-Rod, Jeter and Nomar, and the Cubs landed one of them. In reality, the Cubs ended up giving away pretty much nothing in the trade to get him, but the problem was that he could just never stay healthy.

Nomar hit fairly well when he was on the field but only played 105 games in two seasons combined in a Cubs uniform. He went on to play four more seasons after leaving the Cubs in free agency and played pretty well, especially in 2006, when he went to the All-star game.  Who knows what could have been if he was able to stay healthy in a Cubs uniform, but that is all we have are questions of “what if...”

Ian Stewart

I won’t lie: I was really excited when the Cubs received Stewart in a trade with the Rockies. This was a buy-low deal with hopes that he could return to his 2009-10 form. Well, he never returned to that form, not even close.  In his first season in Chicago, Stewart played only 55 games and barely hit over the Mendoza line (.201). The Cubs actually re-signed him the next season but he was planted in AAA and never got the call from the Cubs. Stewart went on to have a Twitter rant begging the Cubs to release him, which they eventually did.  Good riddance.

Just missed

Anibal Sanchez

False hope fell over Cubs fandom when reports had the team reaching an agreement with Sanchez to be the Cubs ace. I even received a text from ESPN that the Cubs had signed him. Well, we all know that did not end up being true and he re-signed with the Tigers.  Sanchez would have been a welcome addition to the Cubs and the team would have been much better for it.  In 2013, Anibal was lights out with an FIP of 2.39.

Who knows how much of a difference Sanchez would have made for the 2013 Cubs, and it might have paid off even better moving forward. After just missing on Sanchez, the Cubs took a 4yr, $52MM home run cut at Edwin Jackson, a move that really has not worked out for them at all.

Masahiro Tanaka

The Cubs went all-out to try to land Tanaka, and the way he has looked early on with the Yankees has Cubs fans disappointed. It is really too early to get a grasp on what Tanaka will become, but he sure is looking good so far.  There is no question he would be the ace of the staff, with Samardzija and Wood following in the rotation. That rotation sure would look nice and really speed up the rebuild.

When the Cubs missed on Tanaka they ended up signing Jason Hammel, who has been lights out for them so far.  Everyone, including myself, assumes Hammel will be traded at the deadline, an assumption that seems to be correct given how bad the Cubs have been early this season. The Cubs missing on Tanaka could sting for a bit, but again, no one knows how good he will be going forward.

Good eye, Cubs

Brian Roberts

For almost three straight years, from ’06-’08, the Cubs were linked to Brian Roberts, to the point where people were talking as if he was already on the team. It was the right idea at the time: who wouldn't want a switch-hitting All-Star 2nd basemen? We'll never know what kind of extension the Cubs would have given him, or if they would have extended Roberts at all. That's because, in 2009, he received a four-year extension from the Orioles for $40 million.

That 2009 season, Roberts played 159 games, the last season he would play more than 100 games. Since 2009, his highest games-played tally is 77, and that was in 2013. Although he could have been a big help in the playoff years of 2007 and 2008, the Cubs were lucky not to be writing checks to a guy that could barely stay on the field.

Jake Peavy

In an article written by Chuck Garfien, Peavy was even quoted as saying he thought he was going to the Cubs. The year was 2008 and there were reports of a 3-team trade that included Felix Pie and Mark Derosa, as well as possibly trading a young hard-throwing right-hander by the name of Jeff Samardzija. Then in 2009 the White Sox swooped in and pulled of a trade to acquire him, thus ending the Peavy-to-the-Cubs rumors.

Injuries in 2010, 2011 and 2013 limited him to a sparse number of appearances with the White Sox. He did have an All-Star 2012 but was traded a year later to the Red Sox; while he did fetch Avasail Garcia, it was only after the White Sox signed him to a two-year deal after the 2012 season. The way this front office works, and where the Cubs are now, Peavy would have been traded a lot earlier.  I believe the Cubs were again lucky that they did not have to deal with the years of injuries just for the possibility of landing a solid prospect.

Adam Dunn

After the 2010 season, the Cubs were in need of a first baseman after the mid-season trade of Derrek Lee.  Adam Dunn was the focus of the market, with many linking him to the Cubs. The good news for the Cubs is that the White Sox, like they did with Peavy, swooped in and picked up the slugger. Dunn received a 4yr $56Mill deal to be the Chi Sox first baseman and designated hitter.

He then proceeded to have one of the most historically-bad seasons of all time in 2011 with a .159/.292/.277 triple slash; Baseball Reference has him as a -2.9 WAR that season. Although his power stroke returned over the next couple years, hitting 41 and 34 home runs respectively, he still is not a player the Cubs would want given his age and contact issues.

I have witnessed Adam Dunn take batting practice at Wrigley and the buildings across Sheffield must have taken notice as well, but the Cubs sure dodged a bullet not signing Dunn. The 2011 Cubs first baseman was Carlos Pena and he gave the Cubs exactly what they expected. The very next year the Cubs traded for Anthony Rizzo and have their first baseman, hopefully, for the next decade.


A baseball front office is never going to get every trade or free agent signee right, but sometimes they get lucky in the guys they miss.  It would be really nice to have either Tanaka or Sanchez taking the bump every 5th day, but it was also good the Cubs missed on Peavy, Roberts and Dunn.

Trading for Stewart was a mistake and Nomar was always injured, but sometimes a team has to take those chances.  No matter how big or small a difference these players made, or could have made, for the Cubs, some players the Cubs have now would have never been on the team if circumstances were different.  Remember the silver lining in all of this, which is that the Cubs are adding to their core with trades, as well as the picks they have made in the draft.

More talent in the organization means that the Cubs won't be as damaged by the occasional whiff, and that they can be more patient with free agent signings. They won't need to make further knee-jerk signings like the Edwin Jackson deal and will have the necessary prospects to swing a deal for a TOR pitcher without mortgaging the entire farm. Sometimes it's better to let pitches go by, though the Cubs will need to start making contact pretty soon.


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  • Maybe I'm suffering from the recency bias, but I think the Rich Harden trade had the fanbase at least as pumped as the Nomar trade. That had the look of the best team in baseball putting the final piece in place. Then Ryan Dempster walked the world, the infield kicked the ball all over creation, and the dream died a quick, agonizing death.

    So there's some positivity for you all!

  • In reply to Eddie:

    Oh I was a giddy little girl the day they got Harden. So was Mark DeRosa, he told me they got the final piece that summer. It looked good at the time.

  • I should have put him in there! I remember where I was when the Cubs got him. Just finished a baseball game in round lake and checked my phone and got all excited. Also, Josh Donaldson was in that trade and just came off an 8WAR season.

  • I was in the camp that really wanted Stewart to figure it out, and was much in favor of bringing him back that second time. Then he still sucks and crashes and burns on social media right before our eyes ... good riddance.

  • Tommy and I had arguments about it. I was on the Stewart side, he was on the other. He wins...and I am totally ok with it.

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