The Cubs are going to add at least one outfielder to the mix this winter, whether that addition come via trade or free agency. Chicago has lacked a true solution in center field for more than a half-decade now (you can make the case Albert Almora once looked like the answer but that proved not to be the case) - and addressing that hole will be a major focus for the front office this offseason.
In his National League-wide roundup of trade and free agent matches over at The Athletic (subscription required), former GM Jim Bowden ran off a lengthy list of potential fits when it comes to the Cubs, including veteran outfielder Andrew Benintendi.
Cubs need to prioritize an Ian Happ extension early this winter
Had Jed Hoyer and Carter Hawkins traded All-Star outfielder Ian Happ at the trade dealdine last summer, there would be a natural fit for someone like Benintendi. He's just 28 years old, has a patient, on-base focused approach at the dish and already has a Gold Glove to his name in left field. The only problem here is the Cubs didn't trade Happ and he's coming off the most impressive season of his career.
After struggling to find consistency for virtually his entire career, Happ put it all together - building on the momentum he had coming off a strong start to the 2021 campaign. He set multiple career-highs at the dish, posting a 119 OPS+, hitting 42 doubles and driving in 72 runs. Perhaps most notably, he drastically improved from the right side of the plate, which made him a far more dangerous matchup than in years past.
The injuries to top prospects Brennen Davis and Alexander Canario should light a fire under Cubs brass to get something done with Happ this winter, solidifying the team's long-term outfield outlook. This year, the switch-hitting outfielder showed what he can offer Chicago moving forward and, although Benintendi has a higher floor, the upside with Happ is much higher.
MLBTR pegs Benintendi for a four-year, $54 million pact - which definitely wouldn't get something done for Happ. But you can expect a four-year extension offer that also covers 2023, his final arbitration season, somewhere in the $80-$90 million range. Whether or not that would be enough to lock Happ up remains to be seen, but that range feels like a pretty decent jumping off point if you're thinking about what an extension could look like.
The Cubs need to get going on these talks sooner rather than later because if they don't prove to be fruitful, Hoyer will need to pivot quickly - and someone like Benintendi, who is a perfect fallback option, won't be out there long. But if you're asking me to choose between the two, I'm sticking with Happ every day of the week.