Theo Epstein in Chicago: Can he break a second curse?

33 Comments

The first thing most people thought when the rumors of Theo Epstein possibly joining the Chicago Cubs began to circulate was “can he do it again?”  Can the man credited with ending baseball’s most famous world championship drought end baseball’s longest?  Now that Epstein and the Cubs have a deal, it’s worth taking a look at the challenge facing him in Chicago and asking ourselves if Theo Epstein can make lightning strike twice.

There are no guarantees in life, but there is reason to be optimistic about Epstein’s chances to turn the Cubs into a winner. Why? Because many of the same challenges he faced when he took over the Red Sox exist with the Cubs.

Epstein is very familiar with the overall milieu in which the Cubs currently find themselves. When he took over in Boston he inherited a franchise with a dispirited and fatalistic fan base and a team which called a near-dilapidated ballpark home.  He changed the mood soon after he arrived and helped change the narrative as ownership embarked on substantial ballpark renovations.  No, you can’t credit Theo Epstein with all of that — it was John Henry’s dollars which transformed Fenway Park from a place which had seen better years into a perpetually-sold out gem — but Epstein knows what faces the Cubs in this regard.

More substantively, at the top of the Cubs’ list of baseball-needs is fixing a farm system that, while recently spitting out a gem in Starlin Castro, seems to be much better at coming up with role players instead of future stars.  WEEI’s Alex Speier writes today about how back in 2003 Epstein made it his first mission to build a “scouting and player development machine.” While many of Epstein’s big-ticket free agent signings have been busts recently, he and his able assistants — many of whom went on to become general managers themselves — revamped the Red Sox’ player development apparatus.

Indeed, in his first three drafts, Epstein chose Jonathan Papelbon, Dustin Pedroia, Clay Buchholz and Jacoby Ellsbury. It may be hard to see player development as a strength of Epstein’s today given that he’s become more notable for high dollar free agent signings — and given that the young talent that he has acquired in recent years has been dealt to land players such as Adrian Gonzalez — but a steady stream of talent has been developed under Epstein’s watch and such an approach should be Epstein’s first task when he starts work this fall.

Finally there’s the matter of all of that expensive aging talent on the Cubs’ roster.  Yes, we are fixated on the Red Sox’ big bad contracts right now (e.g. John Lackey and Carl Crawford), but it doesn’t take too much effort to look back at what Epstein did in his early years in Boston to see that he’s the right man to fix the Cubs’ case of Chronic Bad and Expensive Syndrome.

Epstein cast off popular but aging and expensive stars like Pedro Martinez and Nomar Garciaparra. He got rid of Manny Ramirez despite his still-elite production when his antics became too much to bear. He made what we forget now were bargain moves like snagging David Ortiz and locking up young stars like Pedroia, Jon Lester and Kevin Youkilis to long-term contracts before they got expensive in arbitration.  He stuck with the then-young and rising Lester and declined to include him in a package for what was thought to be a sure-fire ace in Johan Santana.

Now transfer those examples to the Cubs.  Is there any doubt with that track record that Epstein will be able to figure out that the next winning Cubs team will not have guys like Alfonso Soriano and Carlos Zambrano playing critical roles? Is there any doubt that he’ll be able to ensure that Starlin Castro gets locked up and becomes the centerpiece of the club going forward? That he won’t make shortsighted moves to trade for veterans who, while well-known, aren’t suited for where the team currently finds itself on the success cycle?

Like I said above: there are no guarantees.  If the last month of baseball has shown us, predicting baseball is a sucker’s game.  Epstein may flop in Chicago and the title drought may go to 200 years before it ends.  But as one looks around the game, one would be hard-pressed to find a person more familiar with the challenges facing the Chicago Cubs and with a more successful track record at addressing those exact challenges than Theo Epstein.

It’s a great hire. And one that should give Cubs fans real hope for the first time in a long time.

Noah Syndergaard: ‘I feel like I’m going to bet (on) myself in free agency’

Mike Stobe/Getty Images
5 Comments

Yankees starter Luis Severino and Phillies starter Aaron Nola both signed contract extensions within the last week. Severino agreed to a four-year, $40 million contract with a 2023 club option. Nola inked a four-year, $45 million deal with a 2023 club option.

While the deals both represented significant raises and longer-term financial security for the right-handed duo, some feel like the players are selling themselves short. It has become a more common practice for players to agree to these types of deals in part due to how stagnant free agency has become. Get the money while you can.

Mets starter Noah Syndergaard is in a similar situation as Severino and Nola were. He and the Mets avoided arbitration last month, agreeing on a $6 million salary for the 2019 season. He has two more years of arbitration eligibility left. A contract extension with the Mets would presumably cover both of those years plus two or three years of what would be free agent years. As Tim Britton of The Athletic reports, however, Syndergaard plans to test free agency when the time comes.

Syndergaard said, “I trust my ability and the talent that I have. So I feel like I’m going to bet (on) myself in free agency and not do what they did. But if it’s fair for both sides and they approach me on it, then maybe we can talk.” He clarified that he would be open to a conversation about an extension, but the Mets thus far haven’t approached him about it. In his words, “There’s been no traction.”

Syndergaard, 26, has been one of baseball’s better starters since debuting in 2015. He owns a career 2.93 ERA with 573 strikeouts and 116 walks in 518 1/3 innings. Among pitchers to have logged at least 400 innings since 2015 and post a lower ERA are Clayton Kershaw (2.22), Jacob deGrom (2.66) and Max Scherzer (2.71). Syndergaard made only seven starts in 2017 yet still ranks seventh among pitchers in total strikeouts since 2015.

If Sydergaard doesn’t end up signing an extension, he will be entering free agency after the 2021 season. The collective bargaining agreement expires in December 2021 and a new one will likely be agreed upon around that time. Syndergaard will hopefully have better prospects entering free agency then than players do now.