The most painful trade the Cubs could make at Winter Meetings amid Jed Hoyer doubt

After balking at asking prices for controllable starting pitching this summer and bowing out at the finish line on free-agent right-hander Dylan Cease, the Chicago Cubs' most glaring need is as present as ever with the Winter Meetings right around the corner.

Chicago has assembled a solid mix of mid-to-upper-rotation arms, including Shota Imanaga, Jameson Taillon, and Matthew Boyd, with Justin Steele and Cade Horton also in the mix, having shown the ability to pitch like aces. But there's no clear-cut 'he's getting the ball in Game 1' arm to anchor the staff - and Jed Hoyer is all too well aware of that fact.

The team is rumored to have interest in Japanese right-hander Tatsuya Imai, who will begin visiting MLB teams after the Winter Meetings, but if they continue to refuse to play ball at the top of the free agent market, a trade may be the only logical path forward for the Cubs in their bid to land a high-end starter.

Re-enter the Miami Marlins, who were fielding phone calls left and right on pitchers Sandy Alcantara and Edward Cabrera in the weeks leading up to the trade deadline. The asking prices were astronomical - but given how the Cubs' season ended and the role a lack of impact starting played in their demise, Hoyer may be at least marginally more willing to step up and get a deal done now.

I've banged this drum for months now: if the trade route is the avenue the Cubs take to get that arm, it's going to hurt. You don't get high-caliber players by trading the scraps of your farm system. With that in mind, a pursuit of Cabrera, who has plus-plus stuff and is under team control through 2028 via arbitration, is going to be costly.

Cubs finally land their big arm, but it comes at a significant cost

In this proposed trade, Chicago comes off a pair of top-100 prospects in Owen Caissie and Jaxon Wiggins. My guess is more people are mad about the former than the latter - and if you're worried about losing Wiggins, frankly, the Cubs haven't proven they can develop impact arms internally and, until that changes, I'm not losing a ton of sleep when we deal pitching prospects.

Former top 100 prospect James Triantos also goes to Miami in the deal, along with Ben Brown, whose upside is clear, but has lacked consistency throughout his young big-league career. That gives the Marlins an MLB-ready arm to slot into Cabrera's spot in the rotation and shores up an outfield mix that leaves much to be desired with Caissie.

The Cubs still need multiple moves to rebuild the bullpen - so right-hander Anthony Bender coming over with Cabrera adds a quality middle-relief arm who's under control through 2027. Again, would this be painful, especially watching Caissie - Kyle Tucker's likely successor in Chicago - depart? Absolutely. But pitching prices have never been higher and it might take a deal like this for Hoyer to finally cross this item off his team's shopping list.