The Orioles are headed to the playoffs — and the rise of the O’s has just begun
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David Schoenfield, ESPN Senior Writer
DURING THE SECOND game of the 2023 MLB season, on a cloudy 56-degree day at Fenway Park, the Baltimore Orioles were looking to start the campaign with their second straight win, after barely holding on for a teeth-clenching victory on Opening Day in which they nearly blew a 10-4 lead. The Orioles led 8-7 with two outs and nobody on in the bottom of the ninth. Masataka Yoshida lofted a routine fly ball to left fielder Ryan McKenna, a can of corn in Little League, in high school and certainly in the major leagues.
McKenna dropped the ball.
Adam Duvall followed with a walk-off home run off Felix Bautista.
When the Boston Red Sox won the next day, the early verdict was in: The Orioles were 1-2, had allowed 27 runs and, just as everyone had predicted, didn’t have nearly enough pitching and were destined to finish near the bottom of the tough American League East.
The Orioles have been so methodically consistent all season and now that they’ve clinched a playoff spot while on their way to 100 wins — a mark the franchise last achieved in 1980, by the way — it’s easy to forget that not much was expected from them in March. Though they were surprise winners of 83 games in 2022, the consensus was clear: That wasn’t going to happen again. ESPN forecasted 74 wins. FanGraphs projected 76. None of ESPN’s 28 voters picked the Orioles to win the division — or even to get in as a wild card.
Mea culpa.
The Orioles are leading the best division in baseball, though the Tampa Bay Rays are close on their heels. They’re not that far behind the Atlanta Braves for the best overall record. They are, most definitely, World Series contenders — and they’re going to be in this position for the foreseeable future thanks to general manager Mike Elias’ rebuild that has a chance to rival what Theo Epstein did with the Chicago Cubs and Jeff Luhnow — Elias’ mentor — did with the Houston Astros.
That muffed fly ball has long since been forgotten.
YOU CAN TRACE the Orioles’ turnaround to the first pick of the 2019 MLB draft. Under GM Dan Duquette and manager Buck Showalter, the Orioles had made the playoffs three times from 2012 to 2016, but the fall from those years was rapid and painful: In 2018, the Orioles finished 47-115, becoming just the fifth team since 1900 to lose 115 games. Duquette and Showalter were let go and Elias came to Baltimore from Houston, where he had been the Astros’ scouting director and then assistant GM.
There is always some luck involved when trying to rebuild an organization and the Orioles had the good fortune of having their terrible season at the right time. Oregon State catcher Adley Rutschman was the clear No. 1 talent in the 2019 draft class, one of the most accomplished hitters in NCAA history and a top defensive catcher to boot. The first pick in baseball isn’t always a sure superstar, but everything on Rutschman’s resume pointed to a sure thing.
The pandemic’s impact on minor league baseball delayed Rutschman’s arrival to the Orioles, but things immediately turned around after he was called up in May 2022. The Orioles were 16-24 when Rutschman debuted, then went 60-47 in games he started the rest of the way and 87-51 so far in 2023. They’re an incredible 114-69 when he starts at catcher. The oft-made comparison to Buster Posey is apt. Rutschman may not be a 30-homer slugger, just as Posey never was, but like Posey he gets on base, plays great defense and is that all-important stabilizing personality on the field and in the clubhouse. He may not have the highest WAR on the 2023 Orioles, but there’s no doubt he’s the heart of the team.
While Rutschman was the obvious No. 1 overall pick, the Orioles also hit a home run with the first pick of the second round: high school shortstop Gunnar Henderson. A late riser from Alabama, draft analysts had Henderson potentially going in the first round because of a broad base of skills, but he had faced weak high school competition and most scouts saw him ending up at third base.
Despite COVID wiping out his 2020 season, Henderson soared through the minors and reached Baltimore late last season at just 21 years old. He got off to a slow start, hitting .189 in April and .213 in May, but he has been one of the best hitters in the majors the past four months, slashing .286/.331/.551 with 20 home runs since the beginning of June. Henderson, who turned 22 in June, leads the team in WAR and his raw power is probably his best tool but like so many of the Orioles, he’s a baseball player, in the sense that he does everything well. Via Statcast’s baserunning value metric, Henderson is at plus-4 runs, tied for the major league lead with, among others, speedsters Corbin Carroll and Bobby Witt Jr.
Henderson’s baserunning is par for the course for the Orioles. Maybe it’s a cliché to say they don’t beat themselves or they do the little things well, but they don’t beat themselves and they do the little things well. They’re second behind only the Braves in baserunner advancement, taking the extra base — such as first to third on a single or second to home on double — 49% of the time (the Braves are at 50%). Only three teams have committed fewer errors, they’re top 10 in defensive runs saved and second in fewest stolen bases allowed. They’ve been terrific in one-run games, going 26-12 (and 10-6 in extra-inning games). They’re 10-3 against the Toronto Blue Jays and 8-5 against the Rays.
When you’ve hit rock bottom the way the Orioles did in 2018, you have to hit on draft picks like Rutschman and Henderson, otherwise you’ll need a rebuild to your rebuild — see Tigers, Detroit; or Royals, Kansas City. As Travis Sawchik detailed in theScore in March, the Orioles like to preach something called “growth mindset,” a term first coined by Stanford psychologist Carol Dweck that suggests skills can be learned and improved. During the COVID shutdown, Orioles staffers even met with minor leaguers on Zoom to discuss Dweck’s book. Rutschman and Henderson both bought into the concept.
Of course, the power of a positive mindset isn’t necessarily unique to the age of analytics, but there’s no doubting the Orioles’ player development success under Elias. Indeed, players such as Cedric Mullins, Anthony Santander, Austin Hays and Ryan Mountcastle were all already in the organization when Elias took over; the first three had all reached the majors but had yet to do much. Those four have flourished in recent seasons and produced over 10.5 combined WAR so far in 2023, providing the lineup depth alongside the two young stars (Ryan O’Hearn, purchased from the Royals in January, has been a pleasant surprise and is now the team’s cleanup hitter against right-handed pitchers).
On the pitching side, rookie Grayson Rodriguez was the team’s first-round pick in 2018, the final draft of the Duquette regime. The top-rated pitching prospect in the majors heading into 2023, Rodriguez had a rough start and was eventually sent back to the minors, but he returned after the All-Star break and has a 2.55 ERA over his past nine starts. Bautista was also in the organization since the Orioles signed him in 2016 after the Miami Marlins released him. It took the All-Star closer a long time before he emerged last season, and he was having an even more dominant season in 2023 before recently landing on the injured list with a sore elbow (that could sideline him the rest of the season, putting a damper on Baltimore’s World Series aspirations).
Rebuilding teams also need to make good on minor transactions that usually lead nowhere. Kyle Bradish, the team’s best starter, came over from the Los Angeles Angels as a minor leaguer in 2019 in the Dylan Bundy trade. Rookie setup man (and now closer) Yennier Cano was essentially a throw-in as part of last year’s Jorge Lopez trade with the Minnesota Twins. Starter Tyler Wells, who pitched well early in the season, was a Rule 5 pick in 2020 (also from the Twins). The Orioles signed Aaron Hicks in May after the New York Yankees released him; he was hitting .188 but has flourished in Baltimore with a .296/.385/.475 slash line. Smart and lucky is a good combination.
AFTER THE ORIOLES improved from 52-110 in 2021 to 83-79 last season — the ninth-biggest year-to-year improvement in MLB history — Baltimore fans expected, or at least hoped, that Elias would address the rotation. The Orioles had ranked 23rd in the majors in ERA, 26th in strikeout rate and 25th in FanGraphs WAR — not exactly a playoff-caliber rotation. The big moves were anticlimactic: The team signed veteran innings eater Kyle Gibson to a one-year, $10 million contract and acquired Cole Irvin from the A’s. Thus, the less-than-stellar projections.
There are three ways to view the offseason:
(1) Elias saw the 2022 season as a bit of a fluke, viewed regression as likely and didn’t want to commit big money in free agency just yet, not until it was a sure thing the Orioles were serious contenders. Even though he had said in August 2022 that “our plan for the offseason has always been to significantly escalate the payroll,” this more conservative approach made some sense — even if Orioles fans wanted the club to go after Justin Verlander or Carlos Rodon.
(2) Ownership didn’t provide the checkbook. Definitely possible, especially in light of John Angelos’ comments to the New York Times in August: “The hardest thing to do in sports is to be a small-market team in baseball and be competitive, because everything is stacked against you — everything,” he said. Angelos went on to elaborate: “Let’s say we sat down and showed you the financials for the Orioles. You will quickly see that when people talk about giving this player $200 million, that player $150 million, we would be so financially underwater that you’d have to raise the [ticket] prices massively.” That doesn’t sound like an owner desiring big increases to the payroll — and blaming it on ticket prices.
(3) Elias was simply following the Astros’ blueprint he was once part of: Be cautious, trust your player development — and don’t overspend on big free agents. As the Astros rebuilt, they also had a surprise season, making the playoffs as a wild card in 2015. But that didn’t lead to an emptying of the coffers. When the Astros did need to make a big move, they did it via trades that brought in players with shorter long-term commitments than would have been required to sign a comparable free agent: Verlander in 2017, Gerrit Cole in 2018 and Zack Greinke in 2019. It helped that the Astros made three great trades in which the only significant major leaguer they traded away was Joe Musgrove.
So the Orioles played it safe — but it has worked out. The rotation is still the weakest part of the team, but it has improved to 16th in ERA, 14th in strikeout rate and 17th in FanGraphs WAR. Bradish has made a big leap and has allowed more than three runs just once in his past 16 starts. Rodriguez has lived up to the hype in the second half. Gibson and Dean Kremer have been reliable and not missed a start. The O’s also just got John Means back for his first start since April 2022. The one disappointment has been deadline acquisition Jack Flaherty, who has a 7.16 ERA in six starts with Baltimore.
THE BEST PART of all this, if you’re an Orioles fan: It’s just the beginning. The Orioles have more waves of talent coming. That 110-loss season in 2021 led to another first overall pick in the 2022 draft. Jackson Holliday and Dru Jones, both sons of major leaguers, were the consensus top two talents. The Orioles went with Holliday, not necessarily the slam-dunk choice, and the 19-year-old shortstop has emerged as the top prospect in the minors, rising from Low-A all the way to Triple-A in his first full professional season.
Colton Cowser, the fifth overall pick in 2021, has reached the majors (although he hit .115 in 61 at-bats). Heston Kjerstad, the second overall pick in 2020, had some initial health problems, but he raked in Triple-A and just got called up. Coby Mayo, a fourth rounder in 2020, is just 21, already in Triple-A and, with a .970 OPS, is having one of the best seasons of any minor leaguer. Infielder Jordan Westburg, the 30th overall pick in 2020, is in the majors and has contributed 1.4 WAR in 58 games. All these guys will be competing for playing time in 2024, along with shortstop Joey Ortiz and second baseman Connor Norby, both also raking at Triple-A Norfolk — and the O’s won’t have room for all of them.
Note that these are all position players. The Orioles followed the model that Epstein deployed with the Cubs: Focus on hitters with your early draft picks. Under Elias and scouting director Brad Ciolek, all seven of the team’s first-round picks have been position players. Eight of their nine second-round picks have been position players. It’s one thing to have a strategy, but it’s another to make the right selections and the Orioles have done that.
With so much talent and payroll flexibility, the Orioles can basically do anything they want this offseason. They can make their version of the Verlander or Cole trade. They can sign a couple of free agent pitchers (if ownership is willing to spend money) and let all the young position players battle each other for playing time. Heck, if Shohei Ohtani wants to play for a winner, he should consider heading to Baltimore.
Because there is no doubt that the Orioles are going to do a lot of winning in upcoming seasons. They’re in the playoffs for the first time since 2016 thanks to a perfectly executed rebuilding plan. I’d bet on them succeeding in the next phases of that plan.
Sports
‘You don’t want to have the same drip’: How a Houston Christian receiver became a shoe artist to the stars
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Max Olson
After Texas A&M‘s season-opening win over UTSA in August, Deacon Stanfield made his way down to a tunnel at Kyle Field. KC Concepcion met him there.
The Aggies’ new star receiver was looking to do a handoff. He passed two pairs of his team-issued Adidas cleats to Stanfield. In exchange, the artist promised he would hook him up with more of his finest work.
Custom cleats are a burgeoning business in the era of name, image and likeness, as college football players invest their own money into upgrading their in-game attire. When Concepcion and his Aggie teammates Rueben Owens II, Terry Bussey and Will Lee III are looking for something unique during their 10-0 start, they hit up their shoe guy in Houston.
“That’s the whole thing: You don’t want to look like everyone else, right?” Stanfield said. “You don’t want to have the same drip as the guy next to you.”
Stanfield has worked with Travis Hunter, Ryan Williams and Jeremiah Smith. He’s painted cleats worn by pros such as Travis Etienne Jr., Emeka Egbuka and Carlos Correa. He’s even painted custom Nikes for Caitlin Clark. He’s been customizing shoes for six years — and he just turned 20. What started as a high school hobby has evolved into a successful side hustle. When he’s not spray-painting kicks, he’s playing wide receiver and taking classes at Houston Christian. His teammates at HCU call him “The Cobbler.” Stanfield tries to slow down orders in the fall to focus on being an FCS student-athlete, but he’ll make exceptions when high-profile athletes pop up in his Instagram DMs.
He started this passion in 2019. His art teacher in junior high assigned the class to paint something on an unconventional canvas, so Stanfield tried a pair of shoes. As he watched more tutorial videos on YouTube about the customizing process, he wanted to keep learning and saved up to buy an airbrush and compressor.
“A lot of it was self-taught,” Stanfield said. “I just started, and I ruined so many shoes in the process, just messing with my own shoes.”
His father, Dusty, works in athlete marketing and helped get this hobby kick started with his connections. Deacon painted custom creations for NFL players Trayveon Williams and Case Keenum in 2020, but his first pair that garnered attention were “Duck Hunt”-themed Nike cleats for Hunter Renfrow, a pixelated tribute to the classic NES video game.
“I think with phones and devices taking up so much of their free time, it seems like kids these days are kind of delayed in finding their passion and finding what they really want to do,” Dusty Stanfield said. “So for him to figure that out, it’s something as a parent that’s very fulfilling to see.”
Deacon got opportunities to customize cleats for Etienne and several NFL players as part of the league’s “My Cause My Cleats” campaign. He has also partnered with Panini, which has flown him in for Super Bowl week each of the past three years to create custom cleats for pro athletes at their hospitality suite. Every shoe helps as Stanfield tries to grow his brand and business.
He put on a brave face in a surreal setting for a teen, joking that his “whole body was shaking” as he handed custom Nike sneakers to Eli Manning before this year’s Super Bowl in New Orleans. But nothing compared to the nerves of prepping a pair of Nike Blazer Mid ’77 for Clark to commemorate her Rookie of the Year season with the Indiana Fever.
“She is literally the definition of aura,” Stanfield said. “When she walked in, it felt like the entire room stopped talking and looked at her. When she opened them, she looked over at me and was like, ‘These are so cool. Did you make these?’ It was definitely one of the coolest experiences of my life.”
This is an enterprise that wouldn’t have been possible before the NIL era arrived and modernized college athletics in 2021. It’s run by an active college athlete and supported by athletes who finally have disposable income to spend. Stanfield’s timing couldn’t have been better. And this fall, the Aggies are keeping him busy.
Stanfield did custom sets of maroon, black and white cleats for Bussey and former A&M quarterback Conner Weigman last year and was quickly deluged with more orders. He came up with black Louis Vuitton-themed cleats for linebacker Taurean York and green camouflage cleats for Weigman.
Now he’s producing new shoes for Concepcion, the SEC’s third-leading receiver, every game this season. First it was black cleats with Chrome Hearts brand crosses and then gray Louis Vuitton cleats for the road win at Notre Dame. Stanfield got especially creative for the Aggies’ throwback uniform against Florida, painting an A-10 ‘Warthog’ shark mouth on gold cleats for Concepcion.
It’s not easy to run an airbrush-heavy business out of his Houston Christian dorm room, so Stanfield makes the 30-minute drive home to Fulshear, Texas, on Thursdays, his day off from football, to get his custom orders done out of his garage workspace.
Last Thursday, he put in another marathon session in his workshop customizing four pairs of cleats over 11 hours. Concepcion, Owens, Bussey and Lee got them back just in time to wear them for the No. 3 Aggies’ comeback win over South Carolina.
“I think it’s super cool that Coach [Mike] Elko is relaxed about that,” Stanfield said. “Some coaches won’t let their players wear anything other than black or white.”
HCU coaches have been no less supportive of Stanfield’s entrepreneurship ever since he joined the program last year. The 6-foot, 160-pound scholarship receiver is on the Huskies’ two-deep and travel squad this season and has played six games as a redshirt freshman.
He’s learned how to design mock-ups on his tablet or phone because the prep phase for customizing a shoe can be lengthy.
Stanfield starts by sanding down the shoe’s exterior and wiping it with acetone to strip the original factory finish, taping the soles and areas he won’t paint. Typically, he says, this can take up to two hours — if you’re doing it right.
Once he’s working with a clean canvas, it’s time to airbrush several layers of acrylic leather paint while often incorporating stencils. Stanfield has been doing this long enough that he can mix paint and make Aggie maroon by eyeballing it. After he’s done hand-painting and carefully detailing, the shoes get sprayed with a protective matte finish.
Stanfield can scroll through his camera roll and point to hundreds of cleats and shoes he’s customized, but nothing has gone viral such as the pair he customized for Alabama‘s Ryan Williams last season. Williams ordered a custom pair from him during his senior year of high school and asked for another with his “Hollywood” nickname painted across Nikes last season. After Williams’ breakout performance to beat Georgia, Stanfield did one more for him. Williams gave him creative license to paint whatever he liked.
Stanfield hand-painted a portrait of Williams with red braids over black Nikes. He even recreated the “SC Top 10” chain with gold and silver rhinestones. The pair took him at least 10 hours over several days to produce as he carefully painted the portrait, placed the stones and perfected the details.
Stanfield shared the shoes on his Instagram account, and Williams reposted them after Stanfield had gone to bed. Stanfield’s jaw dropped the next day when SportsCenter’s Instagram account shared his work with the world, in a post that got more than 113,000 likes.
Stanfield typically charges between $100 and $350 for these custom jobs depending on the difficulty.
Some players ship him their team-issued shoes. Others ask him to find a particular pair and add it to the bill. He’s not charging as much as many of the more established creators in this niche industry, mostly because he wants to stay affordable for high school and college athletes.
Keisean Henderson, ESPN’s No. 1 ranked quarterback recruit in the 2026 class, has ordered plenty from Stanfield, including a pair this offseason with his favorite Davy Crockett racoon-skin cap painted on the sides. The Houston commit collaborated with him again this summer on a black Louis Vuitton-style pair covered in UH emojis.
“He is one of one,” Henderson told ESPN. “He can take a thought from your mind and make it reality.”
This is how Stanfield is trying to get his foot in the door in a competitive business by connecting with the next big stars before they blow up. Stanfield did three pairs of custom cleats for Ohio State superstar Jeremiah Smith during his 7-on-7 days with South Florida Express. He would love to work with Smith again, but the Buckeyes don’t wear custom cleats during games.
Some connections endure for years and some pop up in an instant with an unexpected DM. Last summer, he was scrolling through his message requests on Instagram and spotted one from Leanna De La Fuente. She was inquiring about pricing and was looking to surprise her fiancé. When he clicked on her profile and realized she was referring to Hunter, he was astonished and immediately replied.
Stanfield shipped custom black cleats that featured Hunter’s Instagram handle. De La Fuente sent him a thank you video from the two-way star, who promised he would wear them for a game. The artist waited all season, wondering when Colorado‘s Heisman Trophy winner might break them out. Hunter saved the pair for his finale with the Buffaloes in the Alamo Bowl against BYU.
College players who can afford customs are typically wearing them for only one game to complement a specific uniform combination, while high schoolers tend to wear them all season. Henderson, the No. 4 recruit in this year’s SC Next 300, said he currently has four pairs of customs from Stanfield with more to come.
“You can stand out and express yourself without saying words,” Henderson said. “The game of football is made for you to stay in uniform. When I see the opportunity to make it my own, I try my best to showcase how I feel from my cleats.”
Back at Houston Christian, Stanfield tries his best to juggle all his responsibilities. He wore his own work, a pair of orange Louis Vuitton cleats, throughout spring and fall practice with the Huskies. Bachtel credits offensive coordinator Mike Besbitt for starting “The Cobbler” nickname in the spring, and it stuck with teammates. He’s done color swap customs for a few of them, but they know he’s already plenty busy at this time of year. The head coach would like a pair someday, too.
“I told him, ‘Look, I’m not as flashy as you. I don’t need all the Louis Vuitton and all that,'” Bachtel joked. “Just give me something we can wear in recruiting and maybe on the sidelines.”
As much as he would like to someday go full time in shoe customizing, Stanfield says he’s loving his experience in college football and not looking to fast-forward past it. Everybody tells him he’ll miss it when it’s over, so he’s trying to enjoy it. He’ll be back open for business in the offseason and eager to see what creative requests come next.
“I’ve never really thought of it as time-consuming,” Stanfield said, “because it’s a job that doesn’t feel like a job.”
The 2025-26 MLB hot stove has been lit just days after the Los Angeles Dodgers hoisted their second consecutive World Series championship trophy.
All eyes this winter are on a free agent hitting class featuring Kyle Tucker, Kyle Schwarber, Cody Bellinger, Alex Bregman and Pete Alonso. But they’re not the only ones who will make a splash in the market.
Which teams will go big to contend for the 2026 World Series title? And who will make the trades and deals that have everyone buzzing?
Below is a running list of notable transactions and updates from throughout the MLB offseason.
Key links: Offseason grades | Top 50 free agents | Fantasy spin | Best fits
Notable MLB offseason transactions
Nov. 19
The Braves re-signed closer Raisel Iglesias to a one-year, $16 million contract.
The Atlanta Braves acquired Mauricio Dubon from the Houston Astros for Nick Allen in an exchange of infielders.
Nov. 18
The Baltimore Orioles acquired outfielder Taylor Ward from the Los Angeles Angels in exchange for right-hander Grayson Rodriguez.
New York Yankees outfielder Trent Grisham, Detroit Tigers infielder Gleyber Torres, Milwaukee Brewers pitcher Brandon Woodruff and Chicago Cubs pitcher Shota Imanaga accepted their qualifying offers, meaning they’ll return to their respective teams in 2026 at salaries of $22.025 million.
Nov. 17
Reliever Ryan Yarbrough will be back in the Bronx after agreeing to a one-year deal with the New York Yankees.
Nov. 16
First baseman Josh Naylor and the Seattle Mariners have finalized a five-year, $92.5 million contract that has a full no-trade clause and no deferrals, sources tell ESPN.
Nov. 4
Chicago Cubs SP Shota Imanaga becomes free agent after team, player reject options for 2026
Nov. 3
Milwaukee Brewers exercise option on SP Freddy Peralta; SP Brandon Woodruff declines option
Boston Red Sox 3B Alex Bregman opts out of contract; SP Lucas Giolito declines option
New York Yankees OF Cody Bellinger declines option
New York Mets 1B Pete Alonso, RP Edwin Díaz opt out of contracts
Key offseason dates
Nov. 6: Free agency begins at 5 p.m. ET
Nov. 10-13: GM meetings in Las Vegas
Nov. 18-20: Owners meetings in New York
Nov. 18: Deadline to accept or reject qualifying offer
Nov. 21: Non-tender deadline
Dec. 8-10: Winter meetings in Orlando
Dec. 9: MLB draft lottery
Dec. 10: Rule 5 draft
Sports
$400 million extension, blockbuster trade or let it ride? MLB insiders break down Tigers’ Tarik Skubal options
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Kiley McDaniel
After three seasons with a face-of-the-franchise-type superstar to headline the winter, there is no Aaron Judge, Shohei Ohtani or Juan Soto in the 2025-26 free agent class. But there is still one player whose potential availability could rock the offseason ahead: Tarik Skubal.
Why would the Detroit Tigers possibly move their ace on the heels of his second straight American League Cy Young Award and the team’s second consecutive postseason appearance?
Quite simply, because keeping Skubal in Detroit is going to become very expensive, very soon. The 28-year-old left-hander will enter the final year of his contract in 2026 before he is scheduled to reach free agency after the season. If he does hit the market next winter, Skubal has a chance of surpassing Los Angeles Dodgers ace Yoshinobu Yamamoto’s record $325 million contract, and he could even become baseball’s first $400 million pitcher.
With Tigers president of baseball operations Scott Harris facing a decision that will shape the future of the franchise — and impact all of MLB — we talked with 11 industry insiders about what Detroit should do this offseason, broken into three main options.
1. Trade Skubal this winter
This was the least-popular option among our panel and one rival executive explained why.
“The whole reason you do all this is to start a season with a potential contender that has an ace. You can’t throw that away before the season starts. How long will it take to get here again?”
Some panelists hemmed and hawed about how much a team would have to overpay to get Detroit to consider a trade, believing an offer that included a young starting pitcher with front-line potential would be enough to start internal conversations — but nobody could get themselves logically to advocate for a deal unless something completely illogical was offered. And that type of deal increasingly doesn’t happen in modern baseball.
If the Tigers were to trade Skubal for anything less than a gobsmacking return, it would likely mean their competitive window would be tighter — and it would be hard to call Detroit a contender without Skubal next season. Dealing away a player of his caliber would label the Tigers a small-market team, at least by mindset, and bring into question whether they would find themselves in this situation again as other star players approach free agency. It’s much easier to push some, but not all, of their chips to the middle for the upcoming season and see what they can do with Skubal leading the way. Who knows when the next opportunity will come?
When I asked these sources what the Tigers should do, they seemed unsure about how Detroit was viewing the situation but leaned toward believing the Tigers would keep Skubal going into next season. That said, knowing what the market will bear is what Harris likes to do, so the drumbeat of Skubal being available in the right deal — or at least in the sense that Detroit would listen before hanging up — will likely continue.
2. Keep Skubal, but trade him at the deadline if the season doesn’t go as planned
In the event things go sideways during the first half of the 2026 season, everyone on our panel agreed that this was the right move. Defining what “going sideways” means with the expanded playoffs is hard, but battling for a wild-card spot around the trade deadline was where the gray area began for our panelists.
“You cannot, under any circumstances, hold Skubal through the trade deadline and miss the playoffs. That would be a catastrophe,” said one agent.
The haul would still be formidable for a rental deal — back-of-the-envelope math says two prospects ranking later in the top 100 or one elite young player, roughly speaking — but also because the offers would have to clear the bar of Detroit receiving a compensation pick just after the first round to even be considered, as that’s what the Tigers would get if Skubal walked in free agency (under the current free agency system).
Another rival executive has an informed theory on Harris’ focus: “He has his eyes set on 2027 and 2028 as his prime contending years.” If things go well in 2026, the window would expand to include it as well. Top prospects Kevin McGonigle and Max Clark, the No. 2 and No. 6 prospects in the sport, could be core players as soon as the second half of 2026, so aiming for things to really take off in 2027 is logical.
Opinions vary on whether Skubal would fetch more this winter or at the deadline because it’s hard to project how desperate a contender could hypothetically be at the deadline versus what that team would offer to get an entire season of Skubal plus a first-round pick when he walks. It’s safe to assume the return would likely be a bit less at the deadline.
3. Keep Skubal no matter what, try to extend him and take the draft pick if he ends up leaving
This would be a bold move in the era of the asset value-focused approach that so many teams are taking now. If Skubal were to walk in free agency, the compensation would likely be a draft pick in the 30s the following summer — and that’s it. That type of pick is valued at roughly $8-10 million of surplus value, depending on your source.
There is more value that would come before that for Detroit, but it’s hard to quantify. The Tigers would get another title run with the reigning back-to-back AL Cy Young winner and more time to convince him to stay in Detroit. Maybe that combination could make magic and both sides could land on a deal before he hits free agency. Skubal has said he wants to stay in Detroit, so you can’t rule it out. Another rival executive thinks Harris is focused on how to make this happen. “[Harris] will never believe he can’t sign Skubal.”
That being said, Skubal being represented by Scott Boras makes it unlikely he will sign a deal without at least testing the market, as Boras typically advises clients to hit free agency.
There’s one more variable, though, that is unique to the timing of Skubal’s free agency: the expected labor strife next winter, with the current CBA expiring on Dec. 1, 2026. It’s unlikely Boras wants Skubal to be on the market through a labor stoppage that would leave him potentially signing right before spring training after some teams have spent their available cash and with the economic model of the game potentially changing in a way that hurts Skubal’s market. One source said the CBA complication moves the odds that Skubal signs an extension before free agency from 0% to 10%.
The last time there was a labor stoppage hanging over free agency, we saw a frenzy of late-November deals before the Dec. 1 lockout. A similar quicker free agent process that ends with Skubal signing around Thanksgiving would give Detroit a slight leg up, given the familiarity and exclusive negotiating window before free agency, relative to a protracted, winter-long bidding war.
The contract marks to beat are Yamamoto’s $325 million guarantee that is the most ever for pitchers and Max Fried’s $218 million guarantee that is tops among left-handers all-time. Both of those contracts were landed by agencies other than Boras Corp., and setting precedents is a large part of how top agencies market themselves to potential nine-figure clients.
It’s also worth noting Skubal had Tommy John surgery in college and flexor tendon surgery in 2022, which are factors to consider when projecting a long-term deal in free agency.
Are Harris and the Tigers likely to win a straight bidding war with a precedent-setting guarantee? No, but if they can offer a shorter deal at an AAV record with opt-outs, they would at least have a path, albeit a narrow one, to keeping their ace.
The real issue for Detroit is their payroll. They finished last season with a $155 million competitive balance tax (CBT) payroll figure, over $90 million below the first CBT tax threshold. If Skubal will be getting an AAV in the $30 millions or even the low $40 millions, can the Tigers really justify giving a quarter of their payroll to one player? Would Harris do that, or would signing Skubal be part of a larger move to a payroll number that can justify fitting Skubal in there as the Tigers see their peak competitive window opening? If McGonigle and Clark show up late in 2026 and look like future stars, that won’t bump the payroll, but it could make the Tigers look more competitive going forward and that could help their long-term case to Skubal, as well.
This logic — if things go well in 2026, the Tigers will contend and hold onto Skubal through the season — is also why another executive mused on Detroit’s options if it traded Skubal at the deadline. “You could still trade [Skubal] and then sign him back long-term, but I can’t imagine the series of events where that would actually happen.”
There’s also the reading of the tea leaves for this winter. Some sources mentioned Detroit is targeting pitching depth early in free agency. Is that to backfill for a potential Skubal trade? A deal now or at the deadline? Or just to create depth for a title run like all contending teams need? Or to create leverage/depth so they have maximum optionality for all of 2026? You can see what you want to see when it comes to the Rorschach test that is the team-building conundrum of the winter.
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