Cubs News: Five to lock up with extensions right now

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.