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The Twins have a handful of pitchers on their 40-man roster with tenuous holds on their spots. As the front office seeks to upgrade in the offseason, any one of these five players could find themselves at risk of being the odd man out.
Image courtesy of © Rick Osentoski-USA TODAY Sports I'll start out by acknowledging what you already know: young and controllable arms are very valuable in baseball. For that reason, none of these decisions will or should be taken lightly. We've seen countless times how a small shift in pitching role, or a minor tweak to mechanics or pitch mix, can completely turn around a wayward pitcher. 
The Twins won't be eager to move on from any of these five, who have all shown some level of potential while pitching on the big-league stage.
With that said, the front office will likely be seeking to shake things up on the pitching staff this offseason, targeting new talents and projects to take on. There are currently four open spots on the 40-man roster, but those could be claimed quickly as the Twins fulfill needs in the rotation and position-player corps.
After being extended arbitration earlier this month, Jorge Alcala will likely be given every chance to overcome his injuries and make the 2024 bullpen, although that isn't a lock. The following five could be considered less likely to make it through the offseason without exiting the organization via DFA or minor trade.
 

 
Jordan Balazovic, RHP
Heading into the 2020 season, we had Balazovic ranked as the fifth-best prospect in the Twins system. He would move up to the status of No. 1 pitching prospect when Brusdar Graterol – ranked one spot ahead – was traded shortly thereafter. At the time, Balazovic was coming off a stellar year in Single-A, and at age 21 was on track to eventually impact an MLB rotation.
Unfortunately, since the lost COVID season, the righty has struggled with pretty much everything: control, hits, home runs. The 2023 season was especially tumultuous for Balazovic; he missed time in spring training after an off-the-field altercation, and once again got rocked at Triple-A.
He did break through to the majors with 18 appearances, but gave up 12 walks and five homers in 24 innings. A smokescreen of unsustainable early success gave way to the reality of an overmatched pitcher.
 
“Jordan was really good about identifying and being honest with the way he was throwing the ball,” manager Rocco Baldelli said when Balazovic was demoted in late August. “He said, ‘I just have to get in the zone.’ … I liked him taking that level of responsibility on. He was very direct and that felt good. He knows what he’s trying to accomplish.”
Balazovic proceeded to issue 11 walks with four strikeouts in 10 innings for the Saints after getting sent down. A brutal end to a brutal year that leaves the 25-year-old's future here in limbo. He still has some traits to like – namely a big frame and a fastball that can elevate in the zone – but it's fairly to easy imagine the front office moving on and picking a new arm to develop with this roster spot.
Josh Winder, RHP
The Twins were very high on Winder coming out of spring training in 2022, to the point that they surprisingly kept him on the Opening Day roster. He was impressive early on, before familiar shoulder issues cropped up and derailed his season. Winder has since been unable to shake those recurring right shoulder woes, and was limited to just 70 ineffective innings between the majors and Triple-A this season. 
He stands 6-foot-5 with a great slider, giving him a strong reliever profile, and even throws 95 to boot. The problem is that Winder's fastball, despite its velocity, has been a batting-practice pitch in the majors, yielding a .537 wOBA this year and .485 last year. Simply non-viable. He turned 27 in October.
 
Cole Sands, RHP
Sands has been up and down over the past couple of seasons, filling in as needed with 26 appearances (three starts) and 52 innings. The sum result has been a 4.99 ERA and 5.06 FIP – not good. He's in a very similar boat as Winder, running dangerously close to the "Quadruple-A player" designation at age 26 with no real record of MLB success.
I think the Twins will be a little more inclined to keep Sands over Winder because he is younger, has been healthier, and his fastball at least shows signs of being usable. Plus Sands has a really interesting secondary mix that is worth building around as a reliever. 
 
Brent Headrick, LHP
The left-hander was a somewhat surprising add to the 40-man roster last offseason, in that he wasn't really on the prospect radar. The Twins liked his ability to factor as immediate major-league depth, and they were valid in assessing him as such. Headrick made 14 appearances for the big-league club in 2023, handling the load capably at times.
Still, his performance could hardy be described as impressive. Headrick finished with a 6.31 ERA and 6.10 FIP in 26 innings for the Twins. His performance in Triple-A also wasn't great (4.68 ERA in 75 innings) but as a hard-throwing lefty who can provide length and strike people out, I don't think Headrick is especially likely to exit.
Simeon Woods Richardson, RHP
I don't really believe Woods Richardson is at risk of being dumped this offseason, which is why he's at the bottom of this list. He's young enough to have upside, and seasoned enough to offer big-league depth. But the theoretical upside in his game is fading fast.
Woods Richardson's 2023 season was discouraging in almost every way. His velocity dwindled, his stuff lagged and his numbers were dreadful, even though he was seemingly healthy throughout the season. To put his 19.3% K-rate at Triple-A in some context, it was lower than Randy Dobnak's. 
 
The right-hander is still only 23 and I suspect the Twins would at least let him loose in a full-time relief role before letting him loose. That said, it wouldn't surprise me if he was a toss-in for some trade package this offseason.
Managing pitchers like these is a delicate balance. You never want to give up too early, but holding too long can mean costing yourself opportunities to roster and develop different arms. We'll see where the Twins land this offseason on these five fringe figures in the team's pitching plans.
 

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Very true.
Fortunately, you'd be hard pressed to find more incompetent organizations than the Angels and Pirates. Their next logo changes need to be competing Gomer Pyles, one wearing wings, the other wearing an eye patch.
Either way, Seattle and Miami are the teams with pitching to spare but offenses in need, so those would be my prime targets.

Mikolas is still in the rotation, so make your figure 80%.

It tells me someone was willing to offer him at least 3 years and $25M AAV. 
The idea that Gray left because of analytics or frustration in MN says more about the people expressing the opinion than it does about Sonny Gray. They are the ones that are frustrated with the approach. Highly doubt StL is going to treat Gray much differently than the Twins did this season, and Gray is going to be mad almost every time he comes out of the game (and will be over it by the next day. rinse, repeat).

That the Cards made a quick offer that he found acceptable. 
Which may also affirm that he was being honest when he said it wasn’t all about the money. And I’m cool with that. 
For all we know, he may have made the first offer. His agent has a sense of the market. I could easily see someone like Gray saying, “You are near my home, and I like a lot of things about your franchise. If you give me 3/$75M, I’ll sign now and save us both a lot of handwringing over the winter.”

Excellent comments on this thread. 

Sonny is a grouch, but he's not a dunce. He knows that he didn't have two of his best years in career despite the Twins. He bolted because the Cards offer is above market and he didn't dare let them think about it. I wish him well in all his starts except for any potential one against the Twins. 

Three former Twins pitchers will be starting for St. Louis. Sonny Gray, age 34, for the next 3 years at 25 million per year;  300 pound Lance Lynn, age 36, for 10 million in 2024 plus a 1 million buyout in 2025 or a 12 million contract; and old friend, Kyle Gibson, age 36 for 13 million in 2024 and a 12 million team option for 2025. I wish Sonny Gray and Kyle Gibson well.  Lance Lynn...not my favorite. A total of 25m plus 10m plus 12m = $47,000,000 for 2024. Average age of 35.33 years with those 3 new starting pitchers. I am glad the Twins are not on the hook for any of these 3 contracts. Bill Petti wrote an interesting article on Pitcher Aging Curves in Fangraphs published April 30, 2012.  On the average, it does not bode well for the 2024 Cardinals having 60 % of their 5 starting pitchers averaging 35.33 years of age. Plus an aging Goldschmidt, age 36 at 22 million, Arrenado at age 33 at 35 million and Contreras (a 32 year old catcher) at 18 million. The Cardinals are an expensive, old team. With the signings of Gray, Lynn and Gibson, they just got more expensive and older. 

Whatever. It seemed to work for him pretty well. Since joining the Twins he went from a decent/pretty good pitcher to one of the best pitchers in MLB. He'd actually be my number 1 rebound candidate. Anyway, all the best to Gray and all that. 

Yes, but those picks are worth much less than a guy like Brooks Lee. I do think this is a worthwhile addition to seal a close deal. Teams will primarily be looking for players that can play now. Also, teams that are already seeking to add pitchers are not listening on their guys.

Good point, and it raises a further question: at what point does that draft pick become a commodity to the team?  When the ink is dry on the ex-player's new contract?  Or is there some point later when assignments are made officially?

Good for Sonny.  He pitched his tail off for us and we made out well in that trade even if Chase Petty pans out for the Reds.  I'm sure all of us will monitor the comp pick to see what we get and further evaluate this trade down the road.

I was expecting a fourth year that would have nudged the total contract value close to $100M or possibly a little higher.  It may be that Sonny meant what he said when telling us that money wouldn't be the deciding factor, if indeed someone else offered more years.  Of course it's relatively easier to stake out the high ground like that, when life changing money is assured no matter what.  But not that many players take less than the max, at least from all appearances, so maybe it's not "relatively easier" after all.  These guys are tremendously proud human beings, and money is one way they keep score.  Good luck in St Loo, Sonny!

Do I remember correctly that a team can trade away the end of first round compensatory pick? Certainly could see that included in a deal for a #2 pitcher.

It’s also a strategy that they will be employing again this offseason.  If the Mariners are indeed in on Yamamoto, we don’t want to be trading with them before the signing.  Mariners signing Yamamoto would mean the store is wide open for trading others out of their depth.  It’s also going to take quite some time. 

Typically, 'bad news' will occur in Twins fandom, the front office will wait until what seems to be an eternity until we're all foaming at the mouth and tearing each others' throats out, then they'll make a move that will quell the mob.

3 years $25M per is pretty good business on Sonny Gray. Always knew he would get at least a 3 year deal and the number would be north of $20M per season. Only real question was whether someone might give him the 4th year. There's some risk in it, but not too serious. Good move by the Cards.
The combination of money, years, and the lure of the compensatory pick meant there was always going to be little chance of bringing Gray back, but it's ending up being an excellent trade for the Twins. We got a lot of value from Gray over the last 2 seasons and this year he was deserving of every accolade he got. Getting those 2 years plus a pick for Petty is smart business, especially for where the Twins are as a franchise: trying to compete. Petty still looks like a nice prospect, but he has a ways to go. (I wouldn't exactly say he's been bump-free, either: only 68 innings and 18 starts this year? Getting to AA at 20 is impressive, but he still looks another 2 years away even if everything stays on track)
Gray and Maeda are gone, but Ober is ready and Paddack looks back so we're not in the scary place we were 2 years ago when we went out to get Sonny Gray. I still expect them to go get a veteran starter either by signing a guy or making a trade, which pushes Varland back down to AAA to start the season. Lopez, Ryan, Ober, Paddack, and PTBNL with Varland, Festa, and Woods Richardson providing depth will still put us in a good position for the rotation to be a strength again. Hopefully the starter they sign slots above Paddack (in part so they can monitor Paddack's innings in his first full year back from TJ, in part so they're raising the ceiling a little more rather than the floor) but things still look solid.
I just remember that after 2021 we didn't actually have anyone we were sure of in the rotation. Joe Ryan was the closest to a sure thing and he had 5 MLB starts. Ober looked good, but had an injury history (that reared up in 2022). We were talking about maybe bringing back Pineda again. We ended up signing Bundy and Archer, and needed them both. There was This year there's much less desperation and better depth already in place.
Good luck to Sonny Gray (except when he faces us!). Great job while he was here and an excellent trade.

Gray will definitely be missed. He was great to have on the team.

"Broadly speaking, the team has two options: they could acquire a top-tier starter like Corbin Burnes or Logan Gilbert, thickening their bunch at the top of the rotation at the cost of serious prospect capital. The upside in wielding another great starter is obvious, but such a deal would also protect them from the chaos and uncertainty involved in waiting until the trade deadline to make a move, where teams can hike up prices, and the only mercy is for those with stable elbows. Minnesota tried this route once with Tyler Mahle, which may push them to act now. 
They could also go the innings-eater route. Acquiring a Lucas Giolito or Mike Clevinger isn’t sexy, but it would at least give them extra protection if the ligament gods frown upon the team on any given day next year. In the end, the goal should be to knock Varland into the same role Ober occupied in 2023."
If they plan to continue to pace the AL Central and aspire for a championship, doing anything short of getting another top of the rotation arm should be off the table. I'm happy to have them later in the rotation, but Ryan/Ober/Paddock as a #2 starter would disqualify this team as a legit contender. They have to go get another big time arm.
And losing Gray and Maeda changes nothing. This team was NEVER going to sign a top of the rotation arm in free agency. 
 

As first reported by Jon Heyman, then confirmed by Ken Rosenthal, the 2023 AL Cy Young runner-up is a Twin no more. There's an almost golden lining to the cloud, though.
Image courtesy of © Matt Blewett-USA TODAY Sports (Thankfully, Ken Rosenthal is here to cool our senses and establish order, because how comfortable were we with Heyman as the tip of the spear?)
Following a tremendous season that saw him finish as the runner-up to Gerrit Cole for the AL Cy Young, Gray spoke glowingly about Minnesota, emphasizing in a rare public plea that money isn’t the only factor in his decision-making process. Comfort mattered, too, and Minnesota offers that in a unique way. The Twins spun a different tale. Much of their vernacular focused on what Gray had done, and their gratitude for his veteran savvy and excellent pitching. In the moment, this seemed like pretty typical posturing. Recent reporting regarding Minnesota’s future financials revealed the team was dead serious in their callousness.
Today, Gray’s exit will become final. His time with the Twins will go down as the best amongst the four teams for whom he’s pitched. Gray spread a 2.90 ERA over 303 ⅔ frames in two seasons, easily making him one of the best traded-for starters this side of Dean Chance. Among all pitchers with at least 300 innings pitched since the beginning of 2022, only Blake Snell and Justin Verlander beat Gray in ERA. 
He also immortalized himself in recent Twins playoff history, winning the series-clinching game against Toronto with an unforgettable pickoff of Vladimir Guerrero Jr. to end his day. 
Because the team slapped Gray with the Qualifying Offer, the terms of his new deal will hand Minnesota a compensatory pick right after the first round in 2024. That return will soothe the loss of Chase Petty, who was a late first-round pick himself. It isn’t a perfect one-for-one—especially as Petty has worked his way to Double A hiccup-free in the Reds system—but dropping back a few spots in the draft for almost two full years of elite pitching remains an excellent deal. The Twins deserve a lot of credit for their foresight. 
They’ll need that wisdom again as Gray's exit—in combination with Kenta Maeda signing with Detroit—leaves a mangled 2024 rotation to deal with.
Pablo López, Joe Ryan, and Bailey Ober are well-entrenched incumbents, but Chris Paddack (who hasn’t come close to his rookie-year career high of 140 ⅔ innings in four years) and Louie Varland (who pitched much better out of the bullpen in 2023) leave the back end feeling a bit shaky and untrustworthy. Sure, that describes most team’s fourth and fifth starter situations, but Minnesota would probably like to improve their depth, lest an untimely injury forces David Festa into a premature support role.
Broadly speaking, the team has two options: they could acquire a top-tier starter like Corbin Burnes or Logan Gilbert, thickening their bunch at the top of the rotation at the cost of serious prospect capital. The upside in wielding another great starter is obvious, but such a deal would also protect them from the chaos and uncertainty involved in waiting until the trade deadline to make a move, where teams can hike up prices, and the only mercy is for those with stable elbows. Minnesota tried this route once with Tyler Mahle, which may push them to act now. 
They could also go the innings-eater route. Acquiring a Lucas Giolito or Mike Clevinger isn’t sexy, but it would at least give them extra protection if the ligament gods frown upon the team on any given day next year. This plan places pressure on Ryan shedding his gopher-ball habit—something no statistician or qualified religious figure has been able to correctly speak to the potential of. In the end, the goal should be to knock Varland into the same role Ober occupied in 2023.
Either way, the team has plenty of work ahead. That work won’t reach the surface until late December or January—this is Derek Falvey we’re talking about here—but it’ll help define the move-making possible under the self-imposed economic restraints already affecting their structure. We shall see what path they take.

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If you have not seen, the Twins appear to be pretty aggressive about moving Vazquez.    Christian Vazquez Trade
 

Glasnow looks to be the prime target on this list. He's a legit ace assuming he's healthy, and fits the Twins' greatest need. If he has a great year, we could extend a QA, get a draft pick if he signs elsewhere. The others mentioned don't seem as appealing or realistic, although Arozarena is talented. But how about Yandy Diaz as a RH 1B target? He's at $8M annually through 2025. Tampa Bay has Curtis Mead, Jonathan Aranda and Junior Caminero coming at corner IF to backfill Diaz. Tampa may intrigued by the chance to shed around $7M of payroll if they believe one of their young guys can step in for Yandy.

The Tampa Bay Rays have consistently been successfull when trading away expensive players to restock their farm system. Minnesota has multiple needs this winter, and Tampa is a logical trade partner.
Image courtesy of Jonathan Dyer-USA TODAY Sports The Twins and Rays have made multiple trades in the past, and there are clear trade targets on the Rays that fit Minnesota’s needs. The most recent trade between these two clubs came at the 2021 trade deadline when the Twins sent Nelson Cruz and Calvin Faucher to Tampa for Joe Ryan and Drew Strotman. Minnesota clearly won this trade, with Ryan developing into a solid big-league pitcher, and Cruz struggled in his two months for Tampa. 
Overall, the Twins have fared well in trades with the Rays over the last decade. Can Minnesota find another way to get value from players the Rays can no longer afford on their roster? Here are four potential trade targets and how they would fit on the 2024 Twins roster.
Tyler Glasnow, SP
The Twins are potentially losing Sonny Gray and Kenta Maeda from their starting rotation, leaving the front office searching for another playoff-caliber starter. Glasnow returned from Tommy John surgery last season and posted a 3.53 ERA with a 1.08 WHIP and a 162-to-37 strikeout-to-walk ratio in 120 innings. He is due a big bump in pay from $5.35 million in 2023 to $25 million in 2024. The Rays are likely looking to shed his salary since they have one of baseball’s smaller payrolls. Tampa would likely extend him a qualifying offer following the 2024 season, and the potentially recouped draft pick will figure into their asking price for Glasnow. Teams trading for him must provide the Rays with enough value to outweigh an entire season of Glasnow and a late first-round pick. 
Manuel Margot, CF
Finding a center fielder is one of the Twins’ biggest needs for the club this winter. Margot has been a strong defender at all three outfield positions in previous seasons, but his defensive ratings dropped last season while being in his first year back from a patellar tendon strain to his right knee. The Twins might believe he will regain some of his defensive value now that he is a year further removed from his injury. Over the last four seasons, he has posted a 96 OPS+ while hitting .264/.317/.375 (.692). As a righty, his numbers are better versus left-handed pitching with a career .281/.341/.420 (.761) line. He is owed $10 million for 2024 and has a team option for $12 million in 2025.
Harold Ramirez, OF/DH
Ramirez is a right-handed hitter, which the Twins have needed in recent seasons. Last season, he hit .313/.353/.460 (.813) with 19 doubles, 12 home runs, and a 125 OPS+. However, he destroyed left-handed pitchers with a .966 OPS in 124 plate appearances. Defensively, Ramirez doesn’t provide much value, with the Rays mainly using him at DH last season. During the 2022 season, he logged nearly 250 innings at first base, so the Twins could use him as a platoon option with Kirilloff. He is projected to make roughly $4.4 million through arbitration this year, which might be the upper limit for what the Twins want to spend on a part-time player. 
Randy Arozarena, OF
Arozarena is a playoff legend for the Rays and a former Rookie of the Year. Next season will be his first as an arbitration-eligible player, so his cost might start rising, which is usually when Tampa starts to contemplate trading a player. Last season, he hit .254/.364/.425 (.789) with a 120 OPS+ and was elected to his first All-Star team. For the Twins, he is the least likely fit on this list because he is limited to corner outfield duties, and the Twins have multiple options at those positions. He is right-handed, so the Twins might consider a trade for Arozarena if they can trade one of their other outfield options. 
Which player should the Twins target? Is Glasnow’s salary too high for the Twins to absorb? Leave a COMMENT and start the discussion. 

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Why can't the Twins create their own network along the lines of the Yankee's YES network?  Cut out the middlemen and the ad revenues might exceed what they were getting last year.
This would require a lot of work and business expertise, but it seems worth exploring.
 

Keep in mind that reduced TV revenue affects not just the Twins but almost every MLB team, at least to some extent. It seems likely to me that most teams will have more constraints on their 2024 budgets compared to the last few years. I expect free agent contracts to be smaller this offseason than originally projected and there will probably be internal cost-cutting measures instituted, such as fewer scouts and the like. I believe that this would be referred to as a correction in stock market parlance. So the Twins will probably wind up with a payroll ranked in about the same position relative to other teams.