As the MLB offseason rolls along into Monday’s Winter Meetings, we’re mostly left with trying to connect the dots between various reports from various reporters/media types until actual news breaks.

And with that said, there’s been no shortage of reports related to the Red Sox having interest in players across the market - potential trades, big-name free agent signings, the whole deal.

Given that, when Ken Rosenthal reported Friday that the Twins “aren’t anticipating a trade of Joe Ryan,” I immediately started considering what this means for Boston’s offseason plans.

And I landed on this:

With their trade for Pirates righty Johan Oviedo on Thursday, as well as their trade for Cardinals righty Sonny Gray on November 25, the Red Sox are going to save their big money spending for improving the lineup.

What Does Joe Ryan Have To Do With The Red Sox?

Well, unless you’ve been living under a rock, you know that Boston has been linked to the 29-year-old righty since before the 2025 trade deadline, and was seen by many both in the media and around Red Sox Nation as the missing piece for a rotation that was seemingly a true No. 2 away from making a deep playoff push.

That bore out over time, as the Red Sox ran out of arms come playoff time.

Lucas Giolito’s season came to an unceremonious end with an elbow injury, and the Red Sox were forced to lean on young Connelly Early for the third-and-deciding game against the Yankees in the Wild Card Round at Yankee Stadium. And while Early held his own, manager Alex Cora wasn’t ready to push the rookie deep into the game, which he may have for a pitcher with more experience. The Yankees took advantage, beating Boston 4-0 to become the first team to come back from being down 1-0 in the Wild Card Round since MLB changed to the three-game format in 2022.

Had Ryan been on the roster to follow up on Garrett Crochet’s masterful performance in Game 1 of that series, we might be talking about a completely different postseason run for the Red Sox.

So, heading into the offseason, Ryan's continued presence atop most fans’ wish lists made sense. With trade market prices typically lower in the offseason, Boston was expected to be more willing to deal with the Twins for the All-Star at a fairer price than reportedly discussed at the deadline.

The caveat with Ryan is this:

He’s almost certainly going to want an extension anywhere he’s traded, as he faces two arbitration years in 2026 and 2027. Securing his contract now would give him long-term financial security and lock in his salary before arbitration, directly increasing the acquiring team's future payroll obligations.

At his age and after the season he had for a struggling Twins team—3.42 ERA with a 13-10 record across 171.0 innings pitched—Ryan is deserving of some financial security. Securing a long-term contract now could protect him financially from instability if a salary cap is introduced after next season, which players across baseball are anticipating and preparing for by seeking deals early.

This is where it gets tricky for Boston.

Save On One Thing, Spend On Another

MassLive’s Sean McAdam reported on November 30 that Fenway Sports Group is cautious about exceeding the $244 million Competitive Balance Tax (CBT) threshold in 2026 due to “financial penalties and other operational restrictions.” This means every move or reported rumor should be viewed through the lens of whether it fits their self-imposed spending limits.

Even after McAdam’s report, rumors of the Red Sox's interest in free agent hitters remain strong:

- Interest in Blue Jays shortstop Bo Bichette

- Interest in wanting to re-sign third baseman Alex Bregman

- Interest in Phillies slugger Kyle Schwarber, also known around these parts as “Kyle from Waltham”

- Interest in Mets home run derby champion Pete Alonso

- Interest in Japanese superstar Kazuma Okamoto

There’s a reason Boston fans have dubbed this team the “Interest Kings.” Every time a player with some name recognition appears, the Red Sox are linked to them—which is great! But their ability to close on these names has often fallen flat.

If Ryan is off the table and the Red Sox have already added cost-effective starters, their offseason strategy should concentrate on making bold moves for impact hitters. Addressing their offensive needs with significant signings is the clearest path to improving the team.

If they’re going to restrict their spending, maybe the bulk of it will go to guys like Bregman and Alonso. Or Schwarber and Bichette. Or Okamoto and any number of guys out on the market who can help give this team more offense next season.

If it’s just one of the names listed above, fans and media will rip the Red Sox.

If they are not trading for a top-tier pitcher, all significant spending must go toward impact hitters to avoid repeating past postseason failures.

Failure to acquire substantial offensive talent will likely mean another early playoff exit.

​Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.