3 Jameson Taillon replacements Yankees could sign at Winter Meetings

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The New York Yankees’ rotation wasn’t the team’s biggest issue in 2022 — but that doesn’t mean championship-starved fans wouldn’t be pretty psyched to poach Justin Verlander from the Houston Astros or add Carlos Rodón as a fire-breathing No. 2.

Unfortunately, the best the Yankees are probably going to be able to do here is a back-end option to replace the dependable Jameson Taillon, who’s hitting free agency after two years in the Bronx.

Taillon himself could still return, especially in the current wonky pitching climate that includes Tyler Anderson’s All-Star season being rewarded with only a middling three-year deal. Could Taillon sign a similar contract? Maybe a slightly smaller one? Would the Yankees oblige?

It seems safer to speculate about the right-hander’s departure, especially considering the Yankees didn’t unlock much during his time in the Bronx. Taillon arrived as a potential top-of-the-rotation arm beset by injuries, and he leaves having stayed mostly healthy, but without having hit that substantial ceiling. Taillon was good, not great. The Yankees will likely look to replace him with a slightly cheaper, good-not-great arm.

Expect the following arms to all sign deals at the upcoming Winter Meetings, ranging from two highly affordable years to three slightly-tougher-to-stomach seasons.

3 Yankees rotation options who could replace Jameson Taillon in free agency

Jose Quintana #62 of the St. Louis Cardinals (Photo by Harry How/Getty Images) /

3. Jose Quintana

In an unexpected reversal, Yankees fans who expected the team to “settle” for Jose Quintana at the 2022 trade deadline were thrilled to see the team pry away a big fish instead, dealing for Oakland’s Frankie Montas.

Of course — of course — the end result was that Quintana was excellent down the stretch for the playoff-bound Cardinals, while Montas was both injured and unplayable in New York.

Montas will be the team’s de facto No. 4 to open the 2023 season, pending further injury setbacks, which sounds pretty good at face value! Unfortunately, that “face value” doesn’t factor in how much face Montas has to save after he face planted last August and September. Just to be on the safe side, the Yankees should probably import Quintana this time around, too, who’ll only cost about ~$36 million for a three-year deal.

While the left-hander probably won’t be (alright, fine, definitely won’t be) as good as a Yankee as he was with the Cardinals, Quintana rebuilt his value with a 3.4 WAR season spent entirely within the confines of the NL Central. That value is still far from sky high, though, and the Yankees can afford to take a chance on $12 million annually for a 33-year-old who rebounded to post a 2.93 ERA (2.01 down the stretch in St. Louis) alongside top-notch hard contact Statcast numbers (78th percentile in barrel percentage, 89th in hard-hit).

Quintana did more with less than Taillon in 2022, and will make less moving forward as well. The Yankees should be very interested (and probably should’ve been last summer, too).

Chris Bassitt #40 of the New York Mets (Photo by Sarah Stier/Getty Images) /

2. Chris Bassitt

Why all the Chris Bassitt hate in Flushing? Because he’s not Justin Verlander or Carlos Rodón? Man, Mets fans really became Yankee fans quick after decades of making fun of their hubris. Jealously’s a difficult thing.

Scheduled to make the most money out of anyone on this list, Bassitt turned down the qualifying offer, as well as his half of a $19 million mutual option with the Mets (which the team apparently wouldn’t have turned down, considering they floated $19.65 million on the QO). Bassitt clearly values long-term security, but is also probably looking for ~$20 million annually, especially after a 15-9, 3.42 ERA season at the age of 33.

Bassitt as your No. 3 wasn’t quite as appealing as Mets fans had hoped for, once October rolled around. Bassitt and Montas as the Yankees’ 4-5 options, though? Pretty workable, if New York is serious about making their promised upgrades in the name of Aaron Judge sooner rather than later.

The wily veteran is the least-likely name on this list to end up in New York, but would provide an intriguing change-of-pace slotted in between Luis Severino and Montas, in much the same way Nestor Cortes works nicely sandwiched between Gerrit Cole and Severino. That’s a funky rotation, if we’ve ever seen one (and we haven’t, considering the Yankees’ rotation is usually made up of four Darrell Rasners).

Come to the dark side, C. Bass. Be the pitcher Brandon McCarthy was always meant to be back in 2014.

Noah Syndergaard #43 of the Philadelphia Phillies (Photo by Patrick Smith/Getty Images) /

1. Noah Syndergaard

As the Winter Meetings approach, the Yankees’ rotation search all seems to come back to Syndergaard.

He’s got a five-pitch mix, and is over-reliant on sinkers, sliders and changeups, rarely pitching off his four-seamer. That screams Matt Blake. He works out with Eric Cressey, who’s funneled pitchers to the Yankees before via his strength program (Corey Kluber, though it didn’t work so well with Justin Verlander). He’s one more year removed from Tommy John surgery, and though he struggled occasionally last season with the Phillies and Angels, he ended the year with excellent hard-hit numbers, great command, and a 3.94 ERA that approximated Taillon’s work.

The only question remaining is how much it might cost the Yankees to obtain Syndergaard’s next phase.

Last offseason, Thor signed a one-year, $21 million deal with the Angels that felt wild at the time and still feels wild now. Only the Angels apparently didn’t know they were getting a former flamethrower still finding his sea legs.

Who knows whether those extra few miles per hour will ever return to Syndergaard’s fastball? Teams, including the Yankees, likely saw enough to give him three years’ worth of security, but at a price point decidedly below $21 million annually. Try three years and $40 million total, somewhere just above Quintana’s range, considering he might eventually return to power pitching.

Last time around, it was no wonder the Angels won the bidding. They were the only ones who showed up in that particular stratosphere. This time, the Yankees’ Cressey connection seems poised to deliver another back-end, bounce back option.

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