The Cubs had two huge trade chips in starting pitchers Ryan Dempster and Matt Garza, top arms that would yield a wave of minor league prospects—especially pitching prospects—that the team needed to rebuild its organization. To not trade one or either of them would have been a huge disappointment.
Epstein stared that disappointment right in the face as the minutes ticked down to the 3:00 p.m. CT trade deadline.
Dempster had already killed what would have been a good deal with the Atlanta Braves last week. Invoking his "10-and-5" rights (10 years in the majors, five with the same team) to veto the trade that cost the Cubs top pitching prospect Randall Delgado, an arm that could have been one of the best in their future rotation.
The Cubs tried to rebound from the deal falling through by working out a trade with the Los Angeles Dodgers, Dempster's preferred destination. But Epstein and Dodgers GM Ned Colletti could never come to an agreement on a deal.
As the Los Angeles Times' Dylan Hernandez writes, the Dodgers didn't want to surrender a top prospect like Zach Lee for a player who could become a free agent after the season. Colletti also likely felt he didn't have to trade top talent, given that Dempster already made it known he wanted to go to Chavez Ravine.
Last Team Standing
The Yankees showed interest in Dempster, fueled largely by former Cubs pitching coach Larry Rothschild and GM Jim Hendry stumping for him. But Cashman was reportedly not highly motivated to make a deal because the Yankees already have starting pitching. CC Sabathia, Hiroki Kuroda and Andy Pettitte (when he returns) form a strong top three in the rotation.
That left the Rangers, who were extremely motivated to get a starting pitcher.
Even before Colby Lewis suffered a season-ending elbow injury, Texas was looking for a No. 1 type starter for the top of its rotation. That need became even more urgent once the Los Angeles Angels got Zack Greinke, presenting a formidable challenge for the Rangers' AL West lead.
Minutes before the trade deadline hit, the Cubs and Rangers had a deal with Single-A pitcher Kyle Hendricks and third baseman Christian Villanueva joining the load of prospects that Epstein had acquired in the past two days.
Arms and More Arms
The Cubs couldn't trade Garza for full value because of a triceps injury he developed last week that made him unable to pitch until after the July 31 deadline. Even though teams were surely interested in Garza based on past performance, no one was willing to take a risk on a pitcher who hadn't taken the mound in more than a week and whose health was in question.
Epstein was able to compensate for not being able to trade Garza by dealing another starting pitcher. Having already negotiated with the Braves for Dempster, the Cubs were able to work out another trade with Atlanta for left-hander Paul Maholm.
In return, Epstein got two excellent prospects from the Braves. Arodys Vizcaino is coming off Tommy John surgery earlier this year, but was still considered one of Atlanta's top two minor league pitchers. Jaye Chapman has pitched well for Triple-A Gwinnett this season with 60 strikeouts in 53.2 innings.
The other trade deadline deal Epstein pulled off was another trade with the Rangers, sending catcher Geovany Soto to Texas for Double-A pitcher Jacob Brigham.
Brigham wasn't considered a top prospect in the Rangers organization, pitching for the second consecutive season in Double-A. But the Cubs weren't going to get an elite prospect for Soto, who's played in only 52 games while batting under .200. Besides, Brigham has strikeout stuff and racks up innings, two qualities that should get him a shot in the majors.
Waves and Waves of Pitching Prospects
Two weeks ago, when speaking to Chicago reporters, Epstein said the Cubs needed "waves and waves" of pitching prospects coming through the minor league system to help rebuild the organization. One or two arms wasn't going to be enough. The Cubs obviously wanted talent, but they also needed depth.
Four young arms isn't a bad haul for four veteran players, two of whom were likely considered expendable.
Yes, if Epstein had been able to trade Garza and outfielder Alfonso Soriano, he would have collected more arms. But it's possible Epstein could make more deals before baseball's Aug. 31 waiver trade deadline.
Soriano and the $42 million remaining on his contract will surely clear waivers, allowing the Cubs to make a deal. And if Garza gets picked up on waivers, perhaps Epstein can arrange a trade with the club that claimed him.
Outfielders Bryan LaHair and David DeJesus, along with infielder Darwin Barney are another trio of players that could be dealt away over the next four weeks. That could yield another wave of arms into the Cubs' minor league system.
Hoarding prospects and rebuilding with younger players is a completely different way of doing business than Epstein conducted in Boston. With the Red Sox, he could build through trades and free agency. The Cubs obviously aren't to that point.
But so far, Epstein has shown a pretty good talent for building an organization through other methods. The future looks more promising for the Cubs than it did even 24 hours ago. And there should be much more to come.
Follow @iancass on Twitter
Like the new article format? Send us feedback!