Cubs News: Five to lock up with extensions right now

Chicago Cubs: Could extending Baez after a rough year be the smart move?

That being said, Bryant, Rizzo, Schwarber, and Baez will all be on the last year of their contracts in 2021 with the prospect of new bargaining on the horizon after next season. If the organization believes that 2020 was an aberration for some, why not double down after rough years and make a pitch for a team-friendly extension that may be a win-win for player and organization?

When each has a good season in 2021, their asking price in free agency will skyrocket compared with right now, especially if a new collective bargaining agreement favors players even slightly. Plus, with the financial uncertainty of the current situation, there’s the chance that some of these guys would be easier to lock up now versus a future time when finances and health might be a bit more certain after a vaccination.

Who would I specifically look to lock up from the group of core guys?

Baez, for one. Baez is still a positive value and force if only for his defense. He is also on the record saying that the lack of in-game video was a struggle for him. Granted, we’ve seen him swing and miss before, but the flailing was coupled with a lack of fastball hitting that shouldn’t be possible at this point in his career.

If I were a betting man, I’d buy Baez stock low in hopes of a comeback year in 2021. If he’s willing and the Cubs can, a four or five-year extension would certainly be intriguing to me.

Chicago Cubs: With any luck, smiles from these guys could be back in 2021

Schwarber is another guy I’d (for lack of a better term) look to lowball a bit this season. Many still think the guy isn’t perfect, but his exit velocity numbers remain consistently high. With a minor adjustment to his launch angle and aggressiveness in the zone in 2021, there could be many more home runs and doubles.

More from Chicago Cubs News

• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs: It’s time to start thinking about potential September call-ups
• Cubs: P.J. Higgins deserves to be in the lineup on a daily basis
• Cubs might start to limit Justin Steele’s workload soon

Many also forget Schwarber was on pace for a fine 2020 campaign until he suffered a gigantic swoon in September; he couldn’t get right. On September 3, Schwarber was slashing .238/.340/.516, which is basically in line with career numbers.

I’m betting he puts up comparable numbers to that in 2021; if there is a DH in the NL again in ’21, this is an even easier bet to extend him after a rough 2020 season. He cannot only play left field most of the time, but he can also DH on days where a different defensive look might be warranted/desired.

If they’re not going to trade Rizzo or Contreras, I’d also make a play to keep both of them on team-friendly deals. Rizzo seems likely to settle for less money to continue to be in Chicago, where he does so much for the team and community. Four or five more years for a guy who plays first base isn’t the worst idea if you think he’ll bounce back next year.

Contreras is the one guy out of those mentioned thus far who isn’t a free agent after 2021 as he has an extra year to wait. If the Cubs are buying his defensive framing improvements and think he’ll trend the way he did in September, offering him a team-friendly deal isn’t the worst idea. Plus, even if they want to keep Victor Caratini and Miguel Amaya proves ready sooner rather than later, Contreras would continue to be one of the biggest trade chips and assets the Cubs possess.

Chicago Cubs: Could Happ really be the answer to the leadoff curse?

Lastly, another Cub to be bullish on (despite a bit of a fade towards the end of the year) is Ian Happ. Happ had a breakout 2020 after being armed with the heavy confidence of his new manager.

Given the centerfield job, not only did he leave no room for Albert Almora to even think about getting time there, he completely decimated pitchers in the first month and half of the season. Heck, he was even one of the frontrunners for NL MVP into September.

Happ may not have proven his ability to be elite for an entire season, but he had already flashed elite tools before this season that he was able to build on during this past campaign. If Ross and the front office are sold on him remaining in that leadoff spot and occupying centerfield for a few more years, it might be a good time to lock up Happ before he has another year or two like he started 2020.

While he’s not due to become a free agent until 2024, locking up the 26-year old for five or six years might save the Cubs some money down the road in arbitration and beyond if Happ is willing to entertain a team-friendly deal that gives him some big money now.

Granted, changes may come to this offseason, and the organization could look to trade some of the guys mentioned here. While it might be a little harder after down years from most, there’s no doubt that the Cubs could benefit from a more contact-oriented approach.

However, if one or two of those types could be added while getting bounce-back years from all of the core… well… that sounds like the best of both worlds if it’s old friend Tommy La Stella… even better.