Ex-MLB GM's Yankees offseason projection includes bullpen confidence, Red Sox bidding war

The New York Yankees managed to get by with their bullpen in 2026 by the skin of their teeth. A unit that we repeatedly stated needed reinforcements avoided major catastrophes, but saw Tim Hill unravel to the point that he was left off the postseason roster and Brent Headrick begin to run out of gas following his Herculean workload.

Depth in the unit is absolutely something that needs to be improved, though Brian Cashman hasn't always agreed with that statement, but entering the offseason, the Yankees' relief corps is in even more dire straits.

David Bednar is a free agent and the top-ranked closer on the market. Surely there will be a bidding war for his services. Paul Blackburn was a big reason why Cashman's island of misfit toys actually worked out in 2026, but after revitalizing his career as a reliever, he's also hitting the open market, looking to cash in.

Losing one or both of these arms would be a huge blow. New York really needs to bring them both back, and then make more moves to fully solidify the 'pen. Fortunately, MLB insider Jim Bowden envisions good news on the Bednar and Blackburn fronts for the Yankees this winter.

Jim Bowden predicts the Yankees will spend big to retain David Bednar and Paul Blackburn

Bowden ranked the top 40 MLB free agents this offseason in a piece for The Athletic (subscription required) and also predicted ideal landing spots and contract terms for each player.

While many players have multiple ideal destinations listed, Bowden only has one home in mind for both Bednar and Blackburn, and that would be the Bronx. Should that come to fruition, it would be cause for Yankees fans to rejoice.

Interestingly, Bowden sees Cashman opening up the checkbook for both of these key arms, which is something he's mostly shied away from in recent years. Bednar's contract prediction is based on past contracts for high-end closers like Edwin Diaz, Tanner Scott, and Robert Suarez. The proposed deal comes in at three years, $55 million dollars, which looks like money well spent considering Devin Williams got three years, $51 million from the Mets last offseason. Through that lens, shelling out $18-plus million a year seems like a bargain. Putting the qualifying offer on Bednar should help the Yankees, further suppressing his market.

As for Blackburn, the former MLB GM predicts the Yankees will give him two years and $22 million. That's the same deal the Mets gave Luke Weaver last winter, and it's a bit of a risk given the fact that the 32-year-old only has one year of elite production. Still, paying up is a necessary evil, and the Yankees should feel confident that Matt Blake and company fully unlocked Blackburn.

This hypothetical would be a good start, but more will be needed. This simply returns New York to the status quo. The club will still need to find another arm or two, preferably of the high-velocity, high-strikeout variety, either through free agency or the trade market.

Bowden predicts an old-school bidding war between the Yankees and Red Sox for Teruaki Sato

One of the biggest storylines this offseason will be the market for NPB superstar Teruaki Sato. Sato's club, the Hanshin Tigers, has confirmed that it'll honor the slugger's wishes and post him this offseason.

We heard recently from Joel Sherman of the New York Post that the Yankees will look to dump Ryan McMahon this winter, but that pursuing Sato wouldn't be on the docket for New York, citing defensive concerns at third base.

Bowden sees things differently, believing that Sato can stick at the hot corner rather than being forced to move to left field or first base. As a result, he sees the Yankees and Red Sox engaging in the type of bidding war that used to be commonplace between these two rivals.

Sato brings massive power from the left side to the table, but also has some serious swing-and-miss concerns. The scouting report on him is similar to last year's sensation, Munetaka Murakami. Those worries forced Murakami down from a projected $150-plus million deal to a two-year, $34 million contract with the Chicago White Sox.

Murakami's 35-homer campaign reignited the idea that as long as the power translates, the whiffs are acceptable, and could reinvigorate the market for a player who can threaten the league lead in dingers, while also struggling to break the Mendoza line. As a result, Sato could be in line for a big payday.

That's exactly how Bowden sees things playing out, projecting a five-year, $180 million contract for the 27-year-old. Will the Yankees really go that high in order to wrestle him away from Boston? It might be hard to believe. But then again, the urgency to replace McMahon should be sky-high, and even if he's not the perfect option, he can't be worse than the whiff-happy incumbent.

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