If Theo Epstein and Jed Hoyer had drawn up a wish list before the offseason began, Jon Lester would have likely been at the top of it. On Tuesday night, they were able to add a check mark next to his name, signing Lester to a six-year deal worth a reported $155 million.
The news came as a delightful surprise to Cubs fans who were preparing themselves for the worst, waiting for the Boston Red Sox or San Francisco Giants to swoop in and grab Lester out from underneath them. Instead, an offseason that began with the Cubs bringing in Joe Maddon to be their manager has hit a crescendo with the biggest name on the free agent pitching market heading to the north side.
The question now is a simple one for the Cubs: what comes next? The team has already addressed some of their biggest holes, adding a top of the line starting pitcher in Lester, bringing in more rotation depth with Jason Hammel, and bringing in an excellent defensive catcher in Miguel Montero. Other players from the minor league system will certainly be on the way to plug holes, with Kris Bryant likely joining Javier Baez and Jorge Soler sooner rather than later at the big league level.
All of those things are great, but there is still work to be done. Some reporters, including Ken Rosenthal, believe that the Cubs will continue to pursue a big veteran bat to add to their lineup. Whether that means trading for a big-name player like Matt Kemp or Justin Upton, or signing another free agent like Chase Headley, the Cubs could look to accelerate their rebuilding process even more than they already have by acquiring another bat.
Outside of making another big splash, there are still plenty of areas where the Cubs could shore up their roster. Adding another starting pitcher wouldn’t be out of the question, so a guy like Justin Masterson could be an interesting player to keep an eye on. He would likely come cheaper than some other options, and he would add more competition in a rotation that is already significantly deeper than it was over the past few years.
The Cubs could also be looking to move a starting pitcher or two in order to bring in other pieces. Travis Wood could be one of the guys moved, as he would likely yield a nice return in the event of a trade. He would also provide a really nice third or fifth starter for the Cubs, depending on where they would like to slot him, and so Epstein and Hoyer would have to make a tough choice in that regard.
Moving Edwin Jackson’s contract will also be a key thing for the Cubs to do. It will likely mean taking on another contract that a team is looking to unload, but if the Cubs could find the right trade partner, they could turn arguably the biggest mistake of the Epstein/Hoyer regime into less of a misstep.
The Cubs are obviously not where they want to be as an organization, but they are quickly making their way in that direction. With a new manager, a huge free agent acquisition, and a major trade, they have made massive strides toward competing in 2015, and with some more tweaks and additions, they could be poised for an even bigger leap toward World Series contention than they are at the moment.