The Orioles made a splash in the bullpen market, locking down Ryan Helsley with a two-year, $28 million deal that includes an opt-out after the first season. It’s a bold move for a team looking to solidify the back end of its relief corps, especially after a 2025 campaign where late-inning consistency was a glaring issue.
Helsley, when healthy, brings elite-level stuff-his fastball routinely touches triple digits, and his wipeout slider gives him swing-and-miss potential in high-leverage spots. But durability has been the question mark, and that’s likely why the opt-out is in play.
If Helsley dominates in 2026, he can test the market again with even more leverage.
Not everyone’s sold on the deal. The Orioles are getting a high-ceiling arm, but it comes with some risk-hence the C+ grade from Bradford Doolittle.
Still, for a team trying to take the next step, sometimes you have to bet on upside. And Helsley’s upside is as electric as any reliever in the game.
Meanwhile, north of the border, the Blue Jays made a major move of their own, signing Dylan Cease to a massive seven-year, $210 million contract. That’s a long-term commitment to a pitcher known as much for his raw talent as his volatility.
Cease has ace-level stuff-mid-90s heat, a devastating slider-but command has always been the swing factor. When he’s on, he’s nearly unhittable.
When he’s not, it can get messy. Some analysts are skeptical of the deal’s long-term value, including Keith Law, who’s not exactly bullish on Cease’s ability to maintain consistency over that span.
In Boston, the Red Sox are hoping for a bounce-back year with Sonny Gray now in the fold. The club expects Gray to be an upgrade over Walker Buehler, who struggled to stay healthy and effective. Gray, coming off a strong season, brings a mix of veteran savvy and command that could stabilize a rotation that’s been in flux.
As for Bo Bichette, one of the biggest names still on the market, the search for his next home continues. Jordan Schusterman is digging into potential fits for the dynamic infielder, whose bat and glove could be a difference-maker for a contending team. Bichette’s market might take time to fully develop, but there’s no doubt he’ll be a major addition wherever he lands.
Tyler Rogers is another name to watch. He doesn’t light up the radar gun-his fastball is the slowest in the majors-but his funky delivery and ground-ball-heavy approach make him a unique weapon out of the bullpen. Mike Petriello sees him as a sneaky-good pickup for a team looking to add some variety to its relief mix.
With free agency in full swing, R.J. Anderson has identified four potential “Black Friday” bargains-players who may not be headliners, but could provide real value at the right price. These are the kinds of signings that often fly under the radar in December but pay off big in August.
Japanese corner infielder Munetaka Murakami is officially posted, and Jesse Yomtov is breaking down the best fits for the slugger. Murakami brings serious pop and a disciplined approach at the plate, and his transition to MLB will be one of the most intriguing storylines of the offseason.
For those still catching up, Gabe Lacques has his top 20 free agent hitters and relievers still on the board. While some of the biggest names have already inked deals, there’s still plenty of talent available for teams looking to make a late push.
One of the big offseason questions: Will top-tier free agents return to their previous teams? It’s a mixed bag every year, and this winter’s market is no exception. Some players are chasing rings, others are chasing security-and some are chasing both.
In Chicago, the White Sox are still feeling the sting of their deal with Andrew Benintendi. Sam Phalen argues that the contract has been a drag both on the field and in the clubhouse, raising questions about how the team evaluates long-term investments.
Over in Anaheim, the Angels are reportedly working to buy out Anthony Rendon’s contract-a deal that’s become one of the most painful in recent memory. Jack Baer points out an ironic twist: two of the worst contracts in recent history were handed out to players from the 2019 Nationals, a team that won it all but left some financial wreckage in its wake.
Trade rumors are swirling around Mets right-hander Kodai Senga, but the Japanese ace has made it clear-he wants to stay in Queens. Senga doesn’t have a no-trade clause, so the Mets hold the cards, but his preference could factor into any potential deal. Will Sammon reports that the team has been informed of Senga’s stance, and it’ll be interesting to see how that impacts trade talks moving forward.
Looking ahead, Anthony Castrovince is dreaming big with seven “ridiculous” trades he’d like to see. These aren’t your run-of-the-mill swap proposals-they’re the kind of blockbuster ideas that get fans talking and front offices sweating.
Mark Feinsand is playing matchmaker, identifying one player from each team who could be on the move this winter. Some names are expected, others are surprises, but all of them could shift the balance of power if the right deal comes along.
For the new managers stepping into dugouts across the league in 2026, Thomas Harrington breaks down the biggest challenges they’ll face. From managing egos to navigating rebuilds, it’s a tough job-and the pressure starts on Day 1.
And finally, Theo DeRosa poses a fascinating question: Will we ever see a hitter post a .500 on-base percentage again? It’s a tall order in today’s game, but he’s got a few intriguing candidates who might just have a shot.
Free agency is heating up, trade rumors are flying, and the offseason is just getting started. Buckle up-it’s going to be a wild ride.