The bust for Theo Epstein’s Hall of Fame plaque is already on order. Breaking convention, they have decided he’s wearing a baseball cap with the Boston Red Sox logo on one side and the Chicago Cubs on the other. How can it be any other way? After all, he helped his hometown Red Sox break their curse. Then he one-upped it by ending the longest curse in American sports history with the Cubs.
Theo is the face of the Cubs management team, along with GM Jed Hoyer and Sr. VP of Player Development and Amateur Scouting, Jason McLeod. The three musketeers go back to the Red Sox days and are the architects of the defending champion Cubs roster.
When Theo came to Chicago, he spelled out exactly what he was going to do. And he did it. He said he was going to strip the team to the core and rebuild. There was no double-talk. He was honest and respected the fans by being straight-forward from the start.
When you look at names like Kris Bryant, Anthony Rizzo, Jon Lester, Jake Arrieta, and Kyle Schwarber, the normal reaction would be to say job well done. This club was put together with shrewd trades, high draft picks, and free agent signings.
Rizzo was the first acquisition. He was originally drafted by Theo with Boston and Hoyer later traded for him with San Diego. With the gang back together in Chicago, bringing Rizzo into the fold started the transition from cellar-dwellers to a championship organization.
Along with Rizzo , the Cubs pulled off some of the biggest heists in baseball since Theo took over. Jake Arrieta came over from Baltimore along with Pedro Strop for a throwaway free agent the Cubs signed for that exact purpose in Scott Feldman.
Shortstop Addison Russell was snatched from the Oakland A’s for Jeff Samardzija and Jason Hammel in a mid-season trade. Russell started at short in the 2016 All-Star Game and had several key hits for the team last season. 2017 was a down year, but he’s a Gold Glove-level defender and always dangerous in clutch situations.
Game 7 starter Kyle Hendricks was pilfered from the Texas Rangers for Ryan Dempster in a deadline deal. Fortunately for the Cubs brain trust, Dempster turned down a previous trade where the team would have acquired Randall Delgado from the Atlanta Braves.
Arrieta turned into a Cy Young winner in 2015. Then Hendricks finished third in the voting in 2016 for the award. You can say the Cubs made two great tradesa��with their scouting and development team recognizing talent and bringing it to fruition at the Major League levela��but you would be pushing it a bit to say the Cubs knew what they were getting.
They settled for Hendricks after the more-hyped Delgado deal fell apart. Plus, Arrieta was always a guy with potential. He just did not find much success at the big league level until Chicago. A bit of luck was involved, of course. But you need that if you’re going to win.
The draft brought an MVP in Bryant with the second overall pick. Then came Schwarber with the fourth selection in back-to-back years. Bryant was a no-brainer. Meanwhile the Schwarber pick was considered a reach at the time. Albert Almora and Ian Happ were also first-round draft picksa��with Almora coming in Theo’s first draft in 2012 and Happ in 2015.
Outside of the first round selections, the Cubs have nothing to show on the big league roster after six years of drafts, though. And that’s a problem. You would think an organization thought of as being proficient in player development could have at least one player that wasn’t a first-round pick contributing to the team.
Because of the dearth of prospects, especially pitchers ready to perform at the big league level, the Cubs have been forced to trade their best prospects for pitching help. That has put the organization in a bind.
The Cubs have drafted a bunch of arms over the years, but none have had any impact on the major league roster. Hardly any have even had a cup of coffee with the team. It has depleted their farm system to the point where if they are going to acquire more starting pitching in the futurea��and it is neededa��they will have to trade players off of the major league roster.
They need to evaluate their scouting and development process when it comes to pitching. Because even in Boston, outside of Jon Lester, they didn’t do a very good job in that department. Pitching is expensivea��whether you’re spending dollars or players as currency.
In acquiring Aroldis Chapman last year, they gave up their top-ranked prospect at the time in Gleyber Torres. They followed that up by trading the best power prospect in the minorsa��Eloy JimA�neza��along with their best pitching prospecta��Dylan Ceasea��for JosA� Quintana.
The Quintana trade was out of desperation due to their shortage of pitching. I credited Theo for the trades that helped form the nucleus of the club, so I have to call him out when he messes up.
A much better decision would have been trading for Justin Verlander. He wanted to pitch for the Cubs and could have been had for far less in return. Especially if the Cubs took on his full contract. Detroit was looking to dump salary and would have taken a lesser prospect or prospects than they gave up for Quintana.
Verlander was under club control for at least two more years and has been dominant since going to Houston. He is a much better pitcher than Quintana, and was 5-0 with a 1.06 ERA for the Astros after the trade.
The Cubs had the money if they wanted to spend it. If it wasn’t a decree from above that quashed it, Theo really dropped the ball.
Winning the Jon Lester derby before the 2015 season changed the trajectory of the organization. It was a statement move with a top free-agent willing to come to Chicago. The connotation was that change was coming. That it was time for the losing to end. It was $155 million well-spent.
At the opposite end of the spectrum was signing Jason Hayward for $184 million. With his lack of productivity at the plate, he looks more like a defensive replacement than prize free-agent. But on a positive note, we’ll always have his weight room speech during the rain delay in Game 7.
In Boston he threw money down the drain on Carl Crawford, Daisuke Matsuzaka, and John Lackeya��along with a few others for lesser dollars. He gave Edwin Jackson a $52 million contract with the Cubs in 2013. And yet, I look at that as a smart move. It was a terrible pickup, of course. But I am going to let it slide because Jackson kept the Cubs bad enough to get better draft picks. You’ll take that, right?
Theo was decisive when Joe Maddon became available. He realized you needed the right leader for a young core of players, so he jettisoned Rick Renteria after just one year on the job. It was the right decision. I doubt the Cubs would be trying to repeat now if that move wasn’t made.
For the organization to stay on top and compete for a sustained period as Theo promised when he signed on, however, they are going to have to add quality pitching. Arrieta and Lackey are likely gone after the playoffs. The lineup is solid with team control on the players that matter, but you win with pitching. There is work to be done and it’s going to be harder moving forward without the previous depth of prospects.
Negatives aside, if you were told when Theo came aboard the Cubs would make the playoffs three years in a row, win the World Series, and have a chance to repeat, you would saya��where do I sign?
Like the manager, this organization isn’t perfect. They have made mistakes and are going to have to figure out who to keep and who to trade to keep them in the mix. It’s not an easy job.
Winning is never easy in Chicago. But, that’s all they’ve done since coming to the Windy City.