For the Cubs, an in-season Ian Happ trade would signal a total collapse

In just over a week, the Chicago Cubs will kick off the 2023 regular season at Wrigley Field with a new-look roster looking to turn the page on a pair of sub-par campaigns. Both of those years featured major sell-offs at the trade deadline, something the front office is surely looking to avoid this summer.

A lot will have to go right for Chicago to come away with the NL Central crown or sneak into the expanded postseason field. Jed Hoyer and Carter Hawkins know that. The veterans the club brought in will have to perform and some of the young pieces, namely arms, will need to emerge as legitimate big league pieces. Otherwise, a worst-case scenario could emerge: one that puts the team in the 'seller' seat for a third consecutive campaign.

Sahadev Sharma (subscription required) specifically tackled the possibility of an in-season Ian Happ trade should the All-Star outfielder and team fail to come to terms on an extension in the next week or so (which seems awfully likely at this point).

Cubs trading Ian Happ would signify a total failure of a season

Sharma says the likelihood of Happ getting moved if the Cubs are competitive is next to nil - and the optics would be 'awful' after how the last two years played out, regardless of his contract status. Chicago might have to accept that a comp pick in next year's draft is what they're going to get unless they re-sign Happ in free agency, the same path the team wound up taking with Willson Contreras last year.

Happ stands to be one of the top free agent bats available on the open market next winter. Whether or not he can replicate his All-Star, Gold Glove-winning 2022 performance remains to be seen given the inconsistency he's shown in the past but, if he does, he's going to be a big-time name in free agency.

Hoyer, dating back to the Theo Epstein regime, has a long history of failed extension talks with homegrown talent. Some point to the team's outfield prospect depth as a reason to balk on getting a little uncomfortable on a long-term deal with Happ, but as Sharma notes - prospects aren't a sure thing and Chicago's bunch all come with legitimate questions.

He goes on to say Happ has really established himself as an important presence in the clubhouse. His past inconsistencies are concerning, sure, but it makes him relatable to young players looking to get their feet under them at the big league level. The learning curve is steep - but this is a guy who struggled and fought to get to where he is today.

All this to say if the Cubs trade Happ come July, it's a white flag on a rebuild that is still, in all likelihood, is still a year or two away from the organization being a legitimate contender again. From a PR standpoint, it would be nothing short of a disaster - and that aspect, to me, makes an Happ trade highly unlikely barring a total collapse from the club in the first half.