Ranking the 10 best Chicago Cubs moves during the Theo Epstein era

7. Drafting Kris Bryant

Epstein and the Cubs had the second overall pick in the 2013 draft and they took Kris Bryant. This is arguably the most consequential draft pick the Cubs made during the Epstein era, as Bryant quickly became a cornerstone of the franchise and a perennial All-Star talent.

Bryant did great things in the Cubs organization, including winning Minor League Player of the Year, National League Rookie of the Year, the National League MVP, and four All-Star game selections. Bryant's MVP season in 2016, where he posted a 7.3 bWAR with a 148 wRC+, helped carry the Cubs' offense to 103 wins and eventually a World Series title. He was simply an integral cog and the most valuable offensive player of that team.

The only reason this entry isn't higher is because a bit of luck went into drafting Bryant. The Houston Astros could have easily chosen Bryant with the number one overall pick, but they chose right-handed pitcher Mark Appel. Appel was just as coveted a prospect at the time and many projected him to be a frontline starting pitcher in MLB. Unfortunately, things did not work out that way for Appel, and he stepped away from baseball in 2018 and was designated for assignment by the Phillies.

If the Astros had decided to draft another big bat in 2013 and take Bryant first, the Cubs might have chosen Appel. It's extremely unlikely the team would have had the same success in the 2010s without Bryant in his prime.

6. Trading for Kyle Hendricks

One of Epstein's best moves came just nine months into his tenure. At the 2012 trade deadline, the Cubs sent former All-Star pitcher Ryan Dempster - who was 35-years-old at the time - to the Texas Rangers in exchange for Kyle Hendricks and Christian Villanueva. Hendricks was a solid prospect at the time who had amassed 166.1 innings pitched and a 2.65 ERA between Single-A and Double-A. But it's hard to say if anyone expected the soft-tossing 8th-round pick to have the impact he did over the next decade.

In five of his eleven seasons with the Cubs, Hendricks threw at least 177 innings and was an integral piece in the team's starting rotation. He didn't blow hitters away with velocity and his soft-spoken nature made Hendricks' abilities unassuming. But when Hendricks was at his best, he simply threw a lot of strikes and got hitters out.

The crown jewel of Hendricks' career - like many other Cubs - was the 2016 season. He led the entire league with a 2.13 ERA, tossed 190 innings, and made five postseason starts. Perhaps one of the best games of his career was against the Los Angeles Dodgers in the NLCS. The Cubs clinched their first National League Pennant since 1945 behind 7.1 shutout innings from the Dartmouth-alum, who outdueled future Hall of Famer Clayton Kershaw.

Although Villanueva was later non-tendered and never debuted for the Cubs, this trade is still one of the most one-sided deals in recent memory. Epstein traded two months of an aging Dempster for what ended up being 11 seasons of mostly fantastic starting pitching production from Hendricks.

Interestingly, Dempster left Texas to sign a two-year deal with Epstein's former team, the Boston Red Sox. In 2013, he won a championship alongside Hendricks' future World Series teammates David Ross, Jon Lester, and John Lackey.