Few teams have tougher decisions to make this offseason than the Cubs, who are contemplating making serious changes. That means potentially breaking up their World Series core in an effort to add to their farm system and fill needs- third baseman Kris Bryant and catcher Wilson Contreras are two players who could be on the move this offseason. With it looking like 2020 could be a make-or-break year for him and the team, the pressure is certainly on team president Theo Epstein.

Expected Direction: Being Creative To Win In 2020 and Beyond

Cubs Sign RP Ryan Tepera

Contract Details: One Year, Split Arrangement ($900K Majors, $300K Minors)

Grade: 8/10

Given their zero financial flexibility, if the Cubs are going to improve the bullpen, they’ll have to shop at the lowest level. That’s what they’ve done here, as they signed reliever Ryan Tepera to a one-year contract. Tepera, 32, struggled with a 5.23 xFIP in 21.2 innings pitched, but before then, he’d been a very consistent option with xFIPs generally in the low to mid 4.00s. Based on that, there’s not much upside for Tepera, but if Chicago is aiming just to get any sort of extra reliability from their bullpen, perhaps he can provide it at a very cheap cost.

Cubs Trade UTIL Tony Kemp To A’s

Full Trade: Cubs Trade UTIL Tony Kemp To A’s In Exchange For INF Alfonso Rivas

Grade: 8.5/10

In a minor move, the Cubs have traded utility player Tony Kemp to the A’s, acquiring first-base prospect Alfonso Rivas in the process. The 28-year-old Kemp was rather expendable, as they already have utility players such as Ian Happ, Daniel Descalso, David Bote, and Robel Garcia, and in Rivas, they’re acquiring a 23-year-old with tremendous on-base skills, but very little power. There’s not much to take away from it, but rather than just cutting Kemp lose, they do get a decent minor-leaguer, which is worth something.

Cubs Sign OF Steven Souza

Contract Details: One Year, MLB Contract

Grade: 9.5/10

Finally signing a player to an MLB contract, the Cubs have brought in outfielder Steven Souza Jr. on a one-year. Souza Jr., 30, missed all of 2019 and some of 2018 due to injury, and in the 72 games he did play in 2018, struggled to the tune of an 85 weighted-runs-created-plus (wrc+) and a -0.4 fWAR. However, in his last healthy season, he was fantastic with the Rays, posting a 121 wrc+ and 3.8 fWAR; he was a standout performer all around. With expected statistics that line up with that production, it isn’t unreasonable that he could get back to his 2017 form, assuming that he’s finally healthy. If he does, he’ll be a steal for a Cubs team that was in desperate need of a right-handed hitting outfielder. If not, he’s a slim cost for some outfield depth. In other words, this is an excellent low-risk, high-reward type of move.

Cubs Sign RP Jeremy Jeffress

Contact Details: One Year, $850K ($200K Incentives)

Grade: 8/10

Adding a low-risk option to their bullpen, the Cubs have signed reliever Jeremy Jeffress to a $850K one-year deal, with $200K in incentives based on appearances. If you would’ve said a year ago that the 32-year-old Jeffress would be available for under $1 million, I would’ve been stunned. After all, he was coming off a season in which he posted a 2.86 xFIP, and even if he had overachieved, his strong peripherals (10.45 K/9, 3.17 BB/9) gave him a bright outlook for his future. However, he’s been pretty inconsistent throughout his career, and after dealing with shoulder injury, wasn’t the same in 2019. Even though his walk rate (2.94 BB/9) actually got better, he suddenly couldn’t strike out hitters (7.96 K/9), and overall, struggled to the tune of a 4.40 xFIP. Notably, the sinkerballer induced much fewer ground balls last season (48.4%), and though his decreased strikeout rate may seem like a fluke, it doesn’t appear to be considering his fastball dropped two MPH last season. Now, if it was due to the shoulder injury, perhaps he can improve his strikeout rate. However, he’s definitely not a shoo-in to be reliable at this point for the contending Cubs, so this certainly isn’t a heist.

*Will Be Updated With Every Move The Cubs Make