Though some teams have already turned some of their attention toward 2022 while other clubs remain focused entirely on making a 2021 postseason push, they all have one thing in common: Tough decisions loom this offseason.
As we enter the stretch run for the 2021 regular season, here's a look at the biggest question awaiting each team in the coming months.
Note: All stats are entering Wednesday's games
Blue Jays: Will they bring back Robbie Ray?
Last November, the Blue Jays re-signed Ray for one year and $8 million. The numbers won’t look anything like that this winter. Ray is an AL Cy Young Award candidate after completely turning it around in 2021, becoming one of the best stories of the season for the club. The Blue Jays have Hyun Jin Ryu under club control for two more years and José Berríos under control through 2022, but they’ll need to find a way to recreate the strength of the rotation they’re ending with in 2021. Ray is at the heart of that as the team’s ace, and while he’ll rightfully be seeking a significant long-term contract on the open market, one of the first orders of business for Toronto needs to be a decision on Ray. If not Ray, the Blue Jays still need to shop at the high end of the market, but they should be able to use their existing relationship and payroll flexibility to their advantage. -- Keegan Matheson
Orioles: Does Brandon Hyde return in 2022?
The Orioles aren’t commenting publicly on anything related to Hyde’s status, though it's widely speculated the third-year skipper is in the final guaranteed year of his contract and has a team option for 2022. Hired at the foot of their rebuild in December 2019, Hyde was never going to be judged by wins and losses. And by and large, he’s generated stamps of approval from every corner of Baltimore's clubhouse during his tenure to date. Recently, that praise began coming in from the outside as well, with opposing managers going out of their way to compliment the Orioles’ preparation, work ethic and effort during the team’s 19-game losing streak this month. Hyde was brought in to oversee the toughest years of the rebuild, to cultivate an environment focused on development more than on-field results -- and he’s largely done that. A few more wins in September -- or a lack thereof -- likely won’t be the deciding factor. But the longer the front office keeps Hyde’s status a secret, the more it will fuel speculation. -- Joe Trezza
Rays: What will they do with Tyler Glasnow?
Perhaps the most intriguing bit of business the Rays must address is their path forward with ace Tyler Glasnow, who is expected to miss all of next season after undergoing Tommy John surgery in August. Glasnow is arbitration-eligible for two more years, meaning he’ll get a raise from his $4 million salary next year and earn that same pay when he’s healthy and ready to return in 2023, his final season before reaching free agency. Among the Rays' options: releasing him to free themselves of the financial/roster commitment, which seems highly unlikely; keeping him on the roster through the end of his club control, but no further; attempting to extend him beyond 2023, delaying his free agency (likely not something Glasnow would want, keep in mind) in return for guaranteed money; trading him this offseason, assuming another team would be willing to invest heavily in his ‘23 return; or waiting to trade him until later, either after he’s proven his return to full health next year or closer to him becoming a free agent. -- Adam Berry
Red Sox: Can Kyle Schwarber fit on ‘22 Red Sox?
At least offensively, Schwarber has fit like a glove since he joined the Boston lineup on Aug. 13. Can there be a fit beyond this season? There’s at least a chance, given that Schwarber and the Red Sox have a mutual option for $11.5 million that includes a $3 million buyout. The question the Red Sox must ask themselves is this: Can Schwarber fit defensively? In part, that could depend on if J.D. Martinez decides to exercise the final opt-out in his contract. In a perfect world, Schwarber would DH for the Red Sox. But given the quality of Schwarber’s at-bats, the Red Sox could be tempted to keep him regardless of the defensive fit. If Schwarber can gain some comfort at first base, it would make him more appealing for Boston. In that scenario, he could rotate between first base, DH and left field. -- Ian Browne
Yankees: Is Anthony Rizzo a long-term fit?
When the Yankees acquired Rizzo in advance of the Trade Deadline, general manager Brian Cashman said that it was a move made solely with eyes upon improving the 2021 club and its chances of reaching the postseason. As Cashman put it, "We haven't really daydreamed into the future at all." Whenever the Bombers' season ends (and they naturally hope that's in late October or November), they'll have to decide if Rizzo was a short-term fix or a piece for their future. The Yanks have a first baseman under control for 2022 in Luke Voit, whom they shopped prior to the Deadline. Voit will be eligible for arbitration, but he’s affordable, having earned $4.7 million in 2021. Will they allow Rizzo to walk and go forward with Voit at first base, or re-sign Rizzo and attempt to move Voit over the winter? -- Bryan Hoch
Indians: Will they hold onto José Ramírez?
If Cleveland wants to get back to being a serious contender in 2022, Ramírez will likely need to be a key part of the lineup. The front office has indicated that the Indians’ scarce payroll from this season is going to take a jump for next year, and Ramírez’s $12 million option would be a good place to start. The team has no one on its payroll for 2022 at this time, while it decides whether to exercise options on Ramírez and backstop Roberto Pérez. While it’s likely both are picked up, it’ll come down to whether Cleveland will look to trade Ramírez (a trade seems probable for Pérez) before Opening Day. But for a team that’s leaned on Ramírez for the last few seasons as heavily as the Indians have, it seems hard to believe the team would be in a strong position to contend next season without him at third base. -- Mandy Bell
Royals: Will they bring back Michael A. Taylor?
A big hole that the Royals have to fill in the future is in center field. Playing at an expansive Kauffman Stadium, they need someone they can trust to cover ground and play an elite outfield, and that’s exactly what Taylor has done this year. He’s put himself in the AL Gold Glove conversation, and Kansas City will likely explore any interest in a return for 2022, especially because there aren’t any locked-in prospects who will be ready right away to cover center field at "The K." Taylor could be looking for a multi-year contract after what he’s shown this year, so the Royals will have to figure out what the interest looks like on both sides and how Taylor could fit into their future plans in conjunction with the players they have rising in their system. -- Anne Rogers
Tigers: Will they re-sign any of their free agents?
With Jonathan Schoop having signed a two-year extension, the Tigers’ list of pending free agents is down to José Ureña, Derek Holland, Julio Teheran and Wily Peralta. The most intriguing case could be Peralta, who has revived his career this summer with a 3.63 ERA over 12 starts and a relief appearance. But it gets complicated when the Tigers need all the 40-man spots they can muster to protect prospects from the Rule 5 Draft, including Kody Clemens, Will Vest, Reese Olson and Angel De Jesus. -- Jason Beck
Twins: Should they try to keep Alex Colomé?
This should be quite the pivotal offseason for the Twins, who will essentially have to build an entire pitching staff and also make a key decision regarding the future of Byron Buxton. In the earliest weeks of the offseason, one of their first choices will involve Colomé’s $5.5 million mutual option for 2022. On the one hand, Colomé’s early struggles played a not-insignificant role in the Twins’ early plummet this season as he quickly lost his late-inning role and was relegated to low-leverage spots for much of the early summer. On the other hand, he has reemerged as the club’s closer following the Trade Deadline and he owns a 3.43 ERA since May 1. Considering the Twins are on the hook for a $1.25 million buyout as part of the mutual option, it’s a lesser cash value than it seems -- and if they don’t bring him back, Minnesota will have to build most of a bullpen this offseason alongside the majority of a starting rotation. -- Do-Hyoung Park
White Sox: Will Carlos Rodón stay with the White Sox?
Rodón picked a perfect time for the absolute best season of his Major League career, because he'll enter free agency following the 2021 campaign. He has transformed from an injury-plagued starter full of potential, who threw a combined 42 1/3 innings in 2019-20, to a hurler with 163 strikeouts over 114 2/3 innings and a secure spot in the club's playoff rotation. The White Sox have Lucas Giolito, Lance Lynn, Dylan Cease and Dallas Keuchel in their ‘22 rotation, not to mention the move of Michael Kopech from the bullpen. So it will be a tough decision for both sides whether a deal could be reached to keep Rodón with the only team he’s ever known. -- Scott Merkin
Angels: Will they bring back closer Raisel Iglesias?
Iglesias has been a bright spot for the Angels and he has been one of the best closers in the Majors this season. He’s been durable and has registered several multi-inning saves, showing off his versatility. He was acquired in an offseason trade with the Reds and he will be a free agent after the season. The Angels haven’t had a dependable closer like Iglesias in several years and they don’t have an obvious in-house option to close next year. Bringing back Iglesias is high on the club’s priority list this offseason and it’ll be interesting to see if they can get a deal done. -- Rhett Bollinger
Astros: Will they re-sign shortstop Carlos Correa?
Correa cut off negotiations with the Astros when the regular season started, but he hasn’t ruled out returning to Houston. The Astros are still going to make a push to re-sign Correa, who turned down offers of $120 million over six years and $125 million over five years in the spring. Correa, who has ranked in the top three in WAR in the AL for much of the year, isn’t likely to get a $300 million offer from Houston, though. -- Brian McTaggart
Athletics: Can they somehow keep Starling Marte around?
Few Trade Deadline acquisitions have made a bigger impact than Marte, whose electric style of play has brought A’s fans flashbacks of the Rickey Henderson days, with Marte's propensity to steal bases and ability to manufacture runs on his own. The list of suitors for Marte's services will be long this offseason, which is not ideal for an A’s club that operates on a tight budget. They’ve already felt the losses of Marcus Semien and Liam Hendriks, who are having All-Star campaigns this season after signing with the Blue Jays and White Sox, respectively. Could Oakland prevent that from happening again with Marte? -- Martin Gallegos
Mariners: Just how aggressively will they spend in free agency?
Now that the Mariners have brought back Jerry Dipoto and made him the club's first president of baseball operations, how much room will ownership give him to bolster the roster externally? Dipoto has said all along that the Mariners will strike in the free-agent market when the time is right, and with Seattle on the cusp of finishing Year 3 of the rebuild -- and, more chiefly -- being on the cusp of a postseason spot with one month to go, now seems as good a time as ever. And there also will be a bevy of talent in this year’s class that explicitly addresses the Mariners' needs, most notably for power-hitting infielders. -- Daniel Kramer
Rangers: What will the infield look like come Opening Day?
While all eyes are focused on if the Rangers will pursue a big-name shortstop this winter, Texas has a number of other decisions to make across the diamond. Most notably, when will No. 2 prospect Josh Jung make his debut at third base? And, if the club does sign someone like Carlos Correa or Trevor Story, what happens to Isiah Kiner-Falefa, who has held down the position well all season? As the Rangers continue through the rebuild, this will be an important winter and ensuing season for the future of the organization. -- Kennedi Landry
Braves: Will they re-sign Freddie Freeman?
Though the reigning NL MVP Award winner may enter the free-agent market, there is still confidence that he will choose to remain in Atlanta. His desire to spend his entire career with the Braves has been strengthened with the recent Trade Deadline acquisitions, which have brought the team both immediate and potential long-term benefits. Still, this is a deal that likely won’t be completed before the offseason arrives. -- Mark Bowman
Marlins: Will they ink select players to contract extensions?
Miami doesn't have any noteworthy pending free agents, but several players could garner consideration for multi-year extensions over the offseason. Leading the way is Sandy Alcantara, who will be arbitration-eligible for the first time. An All-Star in 2019, Alcantara is the young rotation's workhorse. Other candidates include third baseman Brian Anderson (second year of arbitration eligibility), shortstop Miguel Rojas (vesting option) and first baseman/designated hitter Jesús Aguilar (final year of arbitration eligibility). -- Christina De Nicola
Mets: Will they extend Noah Syndergaard a qualifying offer (and would he accept it)?
Although Syndergaard is likely to make a few appearances down the stretch as a reliever, those brief outings won’t be an accurate gauge of his abilities since he only plans to throw fastballs and changeups. Giving Syndergaard a one-year qualifying offer in the neighborhood of $20 million would be a risky proposition, but it would still likely be cheaper than his price on the open market. The QO would also give Syndergaard a chance to rebuild his value in 2021 before seeking a long-term deal the following winter. While it makes some sense for both sides, there are no guarantees that either party will act accordingly. -- Anthony DiComo
Nationals: Will Ryan Zimmerman return?
It’s hard to imagine the Nationals without Zimmerman, but that is a possibility with the veteran infielder headed for free agency after the conclusion of his 16th season -- all played in Washington. Zimmerman, 36, has thrived in a backup first-base role without the grind of playing every day. It could be easy to envision him back in a similar situation, but the Nationals are moving in a different direction since overhauling the roster at the Trade Deadline -- from contending now to building toward the future. Would that be a fit for Zimmerman for another season? And how are the Nats going to utilize their roster spots to balance veterans and emerging talents? Those questions will need to be answered to determine the future of the longest-tenured member of the organization. -- Jessica Camerato
Phillies: Do they pick up Odúbel Herrera’s option?
The Phillies find themselves remarkably thin in the outfield following years of substandard drafting and developing, which is why Phillies president of baseball operations Dave Dombrowski recently made sweeping changes to the club’s Minor League operations. It is almost a certainty that the organization declines Andrew McCutchen’s $15 million club option for 2022. (It is not a stretch to think that Alec Bohm could be playing there next season.) But what about Herrera’s $11.5 million club option? Herrera has been hot and cold this season, though he has been hitting the ball well for the past month. It is difficult to imagine the Phillies handing center field to Mickey Moniak or Adam Haseley next season. The same holds true for Scott Kingery, who is recovering from season-ending right shoulder surgery. But $11.5 million is high for somebody as inconsistent as Herrera. The bet here is that the Phillies decline Herrera’s option, pay him the $1 million buyout and possibly try to re-sign him for considerably less in 2022. Of course, sometimes it just makes sense to move on. If that happens, two-thirds of the Phillies’ 2022 outfield will likely be brand new. -- Todd Zolecki
Brewers: Time to think about trading Josh Hader?
Obviously, the Brewers love what Hader gives them; the notion they would even let the idea of trading him enter the conversation has all to do with business and nothing to do with performance or intangibles. He is in the conversation for the most valuable reliever in baseball, with a 44.2% strikeout rate that ranks as the best all-time among pitchers who have logged at least 10 innings in the Major Leagues. He is earning a $6.675 million base salary in 2021 after the latest of his arbitration cycles, and he has two more years of club control in ‘22 and ‘23 before he reaches free agency. His value could not be higher at the moment. The Brewers have received calls on Hader in recent years and the asking price was said to be “overwhelming,” as one official put it to FanSided’s Robert Murray earlier this year. As Hader inches closer to the potential of an eight-figure annual salary, would the Brewers consider accepting an offer if another team overwhelms them with a massive haul of Major League-ready talent? This will be the final winter that it can be said Hader has multiple years of control remaining. -- Adam McCalvy
Cardinals: Is Paul DeJong a Cardinal in 2022?
Adam Wainwright has his own decision to make about one more season or retirement. It’s an easy choice for the Cardinals to want him back. But one roster spot St. Louis will have to take a long look at is that of Paul DeJong. The shortstop has had a disheartening season, dancing around a .200 batting average and an OPS under .700. Since his 2019 All-Star campaign, DeJong has slashed just .217/.302/.374 with an 87 OPS+ in 139 games. The emergence of Edmundo Sosa makes the possibility of moving DeJong more sensible, as does the plethora of high-quality shortstops set to be free agents across the league. The Cardinals have preached confidence in DeJong, whom they signed to a record extension through 2025 before he hit arbitration. But might it be time for a change of scenery? -- Zachary Silver
Cubs: Will Ian Happ be a non-tender candidate?
During the abbreviated 2020 season, Happ built on his strong finish to ‘19 with a breakout showing as a trusted center fielder and leadoff man. The switch-hitter batted .258 with an .866 OPS and 133 OPS+ in ‘20, and then earned a $4.1 million salary in arbitration ahead of '21. A cold April (.133/.293/.173) followed and Happ was sporting a .599 OPS as recently as Aug. 12. Since that point, he has been on an offensive tear, slugging against fastballs again and finding a way to get offspeed pitches into the air (a trouble area in the season’s middle months). The Cubs will have to ask themselves, however, which version of Happ is to be believed? The payroll will have ample room to support his salary through arbitration again, but it was just last winter that Chicago made the surprising call to non-tender slugger Kyle Schwarber. Happ likely figures into the ‘22 picture, but that may not be as etched into stone as believed going into this ‘21 season. -- Jordan Bastian
Pirates: Do they try to move Chad Kuhl?
Kuhl’s name appeared a few times in rumors at this season’s Trade Deadline, but nothing happened. However, the Pirates have moved Kuhl to the bullpen since he was on the COVID-19 IL in early August. The Bucs are, first and foremost, trying to build him up to full strength to start, but general manager Ben Cherington said he’s curious to see what Kuhl can do out of the bullpen. Meanwhile, the Pirates have been running with a six-man rotation -- with the sixth man often fluctuating -- to get starting looks for some guys who are on the cusp of the Majors. Will one of these pitchers establish themselves enough down the stretch to block Kuhl out of the rotation, where he posted a 2.91 ERA in July? And if so, could that lead to trade talks opening up again? It seems hard to imagine, but it could be a decision Pittsburgh’s front office will have to consider. -- Jake Crouse
Reds: Will manager David Bell be brought back?
Cincinnati’s manager since 2019, Bell’s three-year contract is coming to an end after this season. He does have an option for 2022. With a near .500 record during his tenure, the Reds endured a losing season in 2019, the club got hot when it counted late in the abbreviated '20 season and made the playoffs before an early exit. In 2021 -- following offseason cost-cutting -- Cincinnati has exceeded expectations and is again contending for the postseason. Credit should go to Bell for keeping the team together amid some key losses, injuries, a bad bullpen and a couple of extended losing streaks. Ownership and the front office has made no indication -- one way or the other -- about what it might do, or when it might do anything, regarding Bell’s status. -- Mark Sheldon
D-backs: Will Torey Lovullo be back as manager?
Lovullo was hired by general manager Mike Hazen just after he took over at the end of the 2016 season and Hazen has already inked him to one extension. That expires at the end of this season and the team has not said, for sure, whether Lovullo will return in 2022. While the D-backs have struggled mightily on the field, both Hazen and team president/CEO Derrick Hall have publicly expressed their support for Lovullo and he has always been an excellent communicator with his players, so he enjoys strong support in the clubhouse. All of that makes it seem likely the D-backs will offer Lovullo a contract, but until it actually happens, it’s something to keep an eye on. -- Steve Gilbert
Dodgers: Will they re-sign Max Scherzer and Clayton Kershaw?
It’s not often that a team has to decide whether they re-sign a couple of Hall of Famers, but that’s the situation the Dodgers will be in this offseason. Scherzer, the team’s big Trade Deadline acquisition, is having another excellent season and will have plenty of offers to choose from this winter. The Dodgers, however, have the advantage that Scherzer has been able to see how the organization works with its pitchers. Kershaw, on the other hand, has been sidelined for two months and his future is a little more uncertain. He’s not one of the elite pitchers in the Majors anymore, but he’s still an effective starter. He’ll have a market this winter, but the possibility of Kershaw wearing any other uniform just feels weird. Los Angeles also has important decisions to make with Corey Seager, Cody Bellinger and Kenley Jansen. It’ll be an interesting offseason for the Dodgers, and it’ll start with Kershaw and Scherzer. -- Juan Toribio
Giants: Which pending free agents will they attempt to re-sign next?
Now that Brandon Crawford’s two-year, $32 million extension has been finalized, the Giants will be able to devote more attention toward attempting to lock up several other members of their roster, including Buster Posey, Brandon Belt, Kevin Gausman and Kris Bryant. Posey has a $22 million team option for 2022, but it’s hard to see him playing anywhere other than San Francisco, so it’s possible that the two sides will try to work out a new deal to ensure that he stays a Giant for life. -- Maria Guardado
Padres: What’s next for Fernando Tatis Jr.?
This question is multi-faceted. First, Tatis needs to make the decision he’s been trying to put off all season long: Will he opt for surgery to repair his balky left shoulder? Tatis has partially dislocated that shoulder at least four times this season, and each recurrence makes another one more likely in the future. Offseason shoulder surgery could set that right. (It would also prompt a race against the clock for the start of the 2022 season). But there’s another question that has arisen since the Padres moved Tatis to right field in an effort to protect that shoulder: Where does he play long term? Tatis has expressed a desire to remain at shortstop once he’s fully healthy. But he’s handled the outfield capably, and there are people in the Padres organization who feel he could be an elite defender there with a bit of seasoning. It’s a massive decision for several reasons -- notably the effect it might have on the team’s best (and highest paid) player. But also for the impact it’ll have on some of the Padres’ offseason decisions, particularly whether to bring back outfielder Tommy Pham and/or whether to trade fellow outfielder Wil Myers. -- AJ Cassavell
Rockies: Is there any chance that a qualifying offer can lead to a new contract for Trevor Story?
This much is known: The Rockies will give Story the qualifying offer to make sure they receive a compensatory pick if Story signs elsewhere. But can Colorado end up re-signing him? The Rockies have made no overtures to Story, but various club officials have warned that his current team should not be counted out of the running. Most believe Story will receive his big contract elsewhere, but it will be interesting to see if the Rockies, who know him best, make a competitive offer. To retain him, however, the club would have to make a couple big splashes to improve the lineup. -- Thomas Harding