Heading into Friday’s 2015 MLB trade deadline, it’s comforting to finally have a competent front office at Wrigley Field.

When thinking about past Cubs trade deadlines – and past trades in general – it’s hard to ignore the amount of Jim Hendry deals now coming to fruition. While there are plenty reminders of bad decisions across the league, Cubs fans have seen the worst.

The relieving part of that is, in the big picture, it only confirms the mess this organization was pre-Tom Ricketts and Theo Epstein.

With the Cubs sitting as “buyers” at the trade deadline for the first time in half a decade – and the first time since Epstein and Jed Hoyer took over – there is a war of ideologies.

One faction of fans and talking heads will say it’s time to buy: If you have a chance to win, take it. The other says protect your young talent like a mother bear protects her cubs (terrible pun, sorry).

The Cubs are in a precarious spot. They have to toe the line between protecting their legitimate future and selling high on certain players.

Thanks to Hendry, the team’s record at the trade deadline has been quite spotty over the years. But on the other hand, as “sellers,” the last three July’s have been quite productive for the Epstein regime. 

The Good 


July 4th, 2014
Addison Russell, Billy McKinney and Dan Straily from Oakland for Jeff Samardzija and Jason Hammel.

C’mon. This is trade deadline highway robbery at its finest – especially because Theo Epstein pulled it off three weeks before the actual deadline. A slam dunk the minute it happened last 4th of July.

Samardzija was tired of losing in Chicago and wanted to be paid like an ace despite being a high-end 3 at best. Jason Hammel was throwing the best ball of his career and immediately re-upped with the Cubs this offseason as the A’s dealt Samardzija to the South Side.

Straily was sent to Houston for Dexter Fowler. McKinney, 20, is four years younger than his competition’s average age at AA and projects as a solid major league outfielder.

But the obvious prize was Russell, who’s already a Gold Glove contender at second base after his call up in late April. The offense hasn’t been great, but at 21 he is still so young that Joe Maddon is making him read books and provide reports while on the road.

July 2nd, 2013
Jake Arrieta and Pedro Strop from Baltimore for Scott Feldman and Steve Clevenger. 

Another proactive, early July sell-off from Epstein that became a home run. Feldman currently has a 4.54 ERA with Houston after Baltimore failed to make the playoffs in 2013, and Clevenger is in AAA.

Meanwhile, the 29-year-old Arrieta has become the Cubs’ best (and most important) starting pitcher after the change of scenery revitalized his promising career. Strop is as solid a 7th inning arm you could ask for, posting a 2.65 ERA in Chicago over three seasons.

Both aren’t going anywhere soon either.

July 31st, 2012
Kyle Hendricks and Christian Villanueva from Texas for Ryan Dempster.

A true deadline deal, Theo’s first major sell-off has worked out exquisitely. Using Dempster’s sparkling 2.25 ERA in Chicago, the Cubs were able to get Kyle Hendricks in return – who has a 3.16 ERA in 32 starts since his call-up last July.

At 25 and not a free agent until 2021, Hendricks appears to have a spot locked down in the Cub rotation for a long time. As a bonus, Villanueva (24) is currently having his best minor league season for Iowa in AAA.

July 23rd, 2003
Aramis Ramirez and Kenny Lofton from Pittsburgh for Jose Hernandez, Matt Brubeck, and Bobby Hill.

Remember Bobby Hill? The perfect example of a “can’t miss” prospect who missed badly. This is going back in time a bit, but worth mentioning because there are some parallels to be drawn from the 2003 team to this year’s team.

Both did and have overachieved a bit early on, with some guys who hadn’t really been there before. But once it became clear the 2003 team was in it for good, the club brought in Ramirez and Lofton for the stretch run and they provided a huge spark. 

Possibly the best move of Hendry’s way-too-long tenure.

The Bad

July 8th, 2008
Rich Harden and Chad Gaudin from Oakland for Josh Donaldson, Sean Gallagher, Matt Murton and Eric Patterson.


At the time, the Cubs were ready to win and Harden was easily the best pitcher on the market. Of course, it looks bad now when you traded a future AL MVP candidate – but Donaldson was a 22-year-old catcher in A-ball at the time.

And Donaldson wasn’t even the “big get” in that deal as Sean Gallagher and Eric Patterson both were projected as more productive major leaguers. C’est la vie.

July 30th, 2009
Tom Gorzelanny and John Grabow from Pittsburgh for Jose Ascanio, Kevin Hart, and Josh Harrison.

The 2009 Cubs needed left handed pitching so they parted with three mid-level prospects for two run-of-the-mill major league lefties. Gorzelanny and Grabow were both unspectacular while Josh Harrison was a late bloomer – coming of age last season for the playoff-bound Pirates as a super utility guy with pop.

Harrison (26) doesn’t have the ceiling that Donaldson has, but he’d be a welcome addition to the 2015 Cubs’ thin bench. 

The Ugly


January 7th, 2011
Matt Garza, Fernando Perez and Zac Rosscup from Tampa Bay for Hak-Ju Lee, Brandon Guyer, Robinson Chirinos, Sam Fuld and Chris Archer.

This wasn’t a trade deadline deal, but it was an egregious error that will go down as the worst of the Hendry era.

After finishing the 2010 season at 75-87, this iteration of the Chicago Cubs was done. Derrick Lee was old, Carlos Zambrano was fully unglued and over-the-hill Alfonso Soriano was over-the-hill Alfonso Soriano. This should have been the offseason where the official rebuild started, but Hendry was trying to save his job.

And he thought Matt Garza would turn the organization around, who finished the previous season with an ERA+ of 100 (exactly league average). 

We’ll get to Archer, but the underrated part of this trade is the four other guys weren’t slouches who disappeared.

Chirinos is a productive catcher for the Rangers.

Fuld is in his 11th big league season as a well-regarded defensive outfielder.

Guyer is a regular for the Rays and Lee remains a top 100 prospect in their system.

But obviously the big loss here is Chris Archer. He was a bonafide blue-chipper that had a 2.34 ERA in his last season with the Cubs organization, and now he’s a 26-year-old in the AL Cy Young race. 

Fittingly, Garza would be traded by Epstein to Texas a week before the 2013 trade deadline. The return haul was solid, as the Cubs turned a clubhouse bum into two productive major league arms (Justin Grimm and Neil Ramirez) with a third (CJ Edwards) knocking on the door in AAA. 

Theo Epstein and Jed Hoyer turning a previous Hendry mess into a positive is the ultimate symbol of how much things have changed in the Cubs front office.

Now, we can only hope they emulate that as trade deadline buyers.

Tim has watched nearly every inning of the Cubs this year, with a lot of that time spent on his couch. Where most beat writers are in and out of press boxes feeding the 24-hour news cycle, Tim sits on the couch and gives his thoughts every few weeks instead. 

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