Chicago Cubs: Re-hashing some of Theo Epstein’s recent draft picks

One of my pastimes is to jump into Major League Baseball draft classes of years past and rework the continuum. Since Theo Epstein joined the Chicago Cubs in 2011, he has made some excellent picks. There are, however, things that could have gone a little differently.

The core of the Chicago Cubs is one of the most impressive in baseball. Who wouldn’t want your offense anchored by Anthony Anthony Rizzo, Javier Baez, and Kris Bryant? Add Willson Contreras into that mix, and it is over. OK, maybe there is a tad bit of bias here, but the four horsemen of the Windy City are some of the best.

Theo Epstein’s work in the annual June draft, especially early on in his tenure while the Cubs enjoyed early picks in the first round, was masterful. He hit on several key guys and built the young position player group he then supplemented with veterans en route to a World Series title.

While today the Cubs still possess a dangerous roster makeup, diving down the rabbit hole of previous draft classes gives perspective on what could have gone differently versus what happened. Spoiler: there are some intriguing scenarios that ‘could have been.’

Chicago Cubs: 2012 1st round – No.6 overall SP Marcus Stroman

Epstein got introduced as the new President of Baseball Operations for the Cubs in October 2011. It gave him eight months to prepare for his first amateur draft as a member of the Cubs. Chicago, in 2011, had a pretty ordinary outfield.

The same happened the next year as well, putting the Cubs into a sort of panic mode as to what to do. Armed with the number six overall pick in a class headlined by Carlos Correa, Epstein selected an outfielder out of Marion Christian Academy by the name of Albert Almora.

At the time, Chicago had a few exciting outfield prospects in Jorge Soler and Trey Martin. The starting pitching was all over the place, riddled with veterans who could barely manage the mound. Enter Marcus Stroman.

Stroman ended up going 22nd overall to the Toronto Blue Jays. Throughout the first few years of his contract, Stroman pitched incredibly consistently. The right-hander made his debut in 2014, going 11-6, 3.65 ERA in 20 starts. Since then, in 120 starts, Stroman has posted a 3.78 ERA with a 115 ERA+.

Almora did not make his debut until 2016. Since Almora has slashed .274/.311/.397 with a .708 OPS, all well below the average of where he should be and what the Cubs had hoped for. Almora is not a bad player. He just has not produced the stats worthy of a number six overall pick. Imagining a rotation of Kyle Hendricks, Jon Lester, Yu Darvish, Jose Quintana, and Marcus Stroman is a fun dream to have.

Chicago Cubs: 2013 1st round – No.2 overall 3B Kris Bryant

The 2013 draft still haunts me, knowing how close the Cubs were to missing on Kris Bryant. Thankfully, the Houston Astros took a hit for Chicago after selecting starting pitcher Mark Appel with the top overall pick.

This one is the most comfortable choice of them all. Bryant slashed .353/.486/.702 with a 1.188 OPS in three seasons at the University of San Diego. In his final year as a Torero, Bryant smashed 31 home runs and carried an OPS over 1.300.

Since then, Bryant has been named both Rookie of the Year and Most Valuable Player and has helped to anchor this Cubs starting lineup. His 2019 campaign was a significant bounce back from the year prior, and still in his prime should have many more years of quality production.

Mark Appel, unfortunately, never amounted to much in professional baseball. Appel was drafted three different times, two of which landed him as a top ten pick. Disappointingly, injuries and inadequate production in the minor leagues led Appel to retire in 2018. For the Cubs, this will always be the draft where Bryant was the guy who almost got away.

Chicago Cubs: 2015 1st round – No.9 overall SP Walker Buehler

Following a better but still disheartening 2014 season, Epstein and the Cubs found themselves once again in the top ten for the draft. At number nine overall, Chicago selected Ian Happ, a multifaceted talent, as a way to add to the depth of the outfield.

Fast forward fifteen picks, and you have Walker Buehler finding himself in Dodger blue. The right-hander had previously been selected in 2012 by the Pittsburgh Pirates. Choosing at the time not to sign, Buehler instead attended Vanderbilt University to join their vaunted baseball program.

Happ, meanwhile, attended the University of Cincinnati for two years before the draft. He immediately signed with Chicago. Happ put up near-identical slash lines as a Bearcat, hitting .322 in each of his two seasons. Buehler was equally impressive in his college career. He finished three seasons with the Commodores, posting a career 2.87 ERA in the process.

To the Cubs’ credit, at the time, they needed outfield depth. The 2014 trio of Chris Coghlan, Arismendy Alcantara and Nate Schierholtz were not cutting it. Also, Happ has not been terrible. In his first season in Chicago, he hit 24 home runs in 115 games and posted a 114 wRC+. In the time since Happ has struggled. This season he did bounce back in a big way, which is great to see.

Buehler meanwhile has become the new king for the Los Angeles Dodgers. Within a year, Buehler was in the major leagues. His first stint was less than ideal; however, within the last two seasons, Buehler has carried a 2.98 ERA in 53 starts. Yeah, pretty good. The Cubs signed Lester the year before, so that is probably why Happ ended up being the pick. Still, thinking about Walker Buehler in Cubbie blue is a dream come true.

Chicago Cubs: 2016 3rd round – No. 104 overall 2B Cavan Biggio

This one is fun and still fits the mold. The Cubs in 2016 did not have a first-round pick. The club also did not have a second-round pick. In the third round, at number 104 overall, Chicago selected a pitcher out of the Oklahoma State University named Tom Hatch.

Hatch was up and down at OSU. In his first season, Hatch posted a 5.28 ERA in nine starts. The following season, Hatch bounced back, posting a 2.14 ERA in 19 starts. Cavan Biggio was in a similar spot at the University of Notre Dame, finishing with a career .272/.406/.425 line in 167 games.

Biggio ended up going to the Toronto Blue Jays two rounds later. Reaching on Biggio would have given the Cubs the stability they have so desperately needed for a couple of seasons now. Addison Russell has never been the answer. Bringing Biggio in would have given him a clear path to the majors within a year or two.

However, Biggio only made his major league debut this season, so maybe things wouldn’t have been different in that span. The 24-year-old displayed his talent, slashing .234/.364/.429 with a 114 wRC+. Biggio was also worth 2.4 WAR, hitting 16 home runs with 14 stolen bases. A middle infield with Báez and Biggio is a fun one to imagine.