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KNOXVILLE, Tenn. — The roar of the Neyland Stadium crowd was still ringing in Tennessee coach Josh Heupel’s ears when he finally got home late Saturday night.

“And that’s a good thing,” Heupel told ESPN. “There’s always the next game, but a scene like that is something you don’t want to forget. I’ve never seen anything like it.”

He hopes to see a lot more like it, as does a suddenly recharged Tennessee fan base that is basking in Saturday’s 38-33 win over Florida, a game that, in typical fashion for this series, went down to the very end.

It was also a game, at least in the eyes of long-suffering Tennessee fans, that looked all too familiar in those final frantic minutes. Florida clawed back from a 38-21 deficit midway through the fourth quarter, and after recovering an onside kick, the Gators had one final heave by quarterback Anthony Richardson from the Tennessee 39-yard line to win it.

Tennessee defensive end Byron Young hit Richardson as he released the pass, and cornerback Kamal Hadden had an easy interception at the 6-yard line to seal the game.

Only then could Heupel or anybody wearing Tennessee’s shade of orange (Pantone 151) exhale.

“It’s like a punch-drunk fighter. You’re just waiting for that next blow to come,” said Tennessee fan Rusty Rathburn, who made the trip from Portage, Michigan, along with sons Luke and Max to see his alma mater accomplish something it has done only twice in the past 18 years — beat Florida.

“We’ve had so much misery against these guys. You’re waiting for us to screw it up. But this team is different.”

Similarly, Heupel spent all week hammering home to his players that this was a different team, different game, different year. And, yet, he was also keenly aware of how deeply the scars run among the Big Orange faithful when it comes to the Gators, who had dominated this rivalry back to the height of Phillip Fulmer’s successful tenure at Tennessee, when even some of his most talented teams didn’t have an answer for old nemesis Steve Spurrier.

So, yes, Heupel soaked up the moment with his players and the fans, most of whom remained in the stands covered in orange-and-white checkerboard for nearly 20 minutes after the game.

“I love the pride and the passion of our fan base, and I can promise you that our players feel every bit of it,” Heupel said.

Indeed, Neyland Stadium was electric, bursting at the seams, as the Pride of the Southland marching band played “Rocky Top” loud enough and long enough for it seemingly to be heard in every corner of the state, from Mohawk to Union City and all points in between.

It’s true this was hardly the best Florida team that Tennessee has faced over the years. After all, the Vols were 10½-point favorites, the most they’ve been favored in the series since the 1970s. Billy Napier is in his first season as Florida’s coach, and the Gators have some big holes to fill on their roster.

Still, it was Florida, and as Spurrier himself put it last week, “It just seems like a whole lot of good things always happen to the Gators in this game and a whole lot of bad things happen to the Vols.”

So who could blame the Big Orange Nation for partying like it was 1998, the year of the Vols’ last national championship? The party might continue for a while with Tennessee having a bye week this Saturday.

“It’s surreal, to be able to come here and really just experience this and see how it’s all changed from when I first got here until what it is now,” junior defensive tackle Omari Thomas said. “It’s something we want to keep building on, and honestly, get it better and better each week.”

Saturday’s postgame scene will be hard to match.

Former players from five different decades flocked to Heupel to hug him. They hugged current players, and they hugged each other. Heath Shuler was there. So were Al Wilson, Josh Dobbs, two generations of Colquitts (Craig and Britton) as well as Jabari Davis and Fred White, who weren’t bashful about lighting up victory cigars.

Arian Foster, a four-time Pro Bowler, was back at Neyland for the first time since he played his final game at Tennessee during the 2008 season.

“I can promise you that I will be back,” said Foster, who led the NFL in 2010 with 1,616 yards rushing.

Tony Vitello, Tennessee’s fiery baseball coach, had done his part to fire up the crowd before the game, and he was a buzz saw afterward. Earlier in the week, he said his biggest goal was to not get arrested.

It appears he achieved that goal and didn’t chest-bump any officials (or umpires), either. Vitello even joked on the set of ESPN’s College GameDay before the game that “if we win, everybody could go streaking.”

It was that kind of day on Rocky Top, a breakthrough of sorts for a football program that has wallowed around in a gator-infested wasteland for most of the past two decades. Entering Saturday’s game, the Vols had more coaches (six) than they had wins over the Gators (five) in the previous three decades.

Wilson, who was inducted into the College Football Hall of Fame last year, speaks for the entire Tennessee fan base when he says he still feels the pain of those Florida losses going all the way back to the 1990s.

“I lost five games my whole college career, and three of them were to Florida. I mean, come on. We were sick of losing to them and sick of hearing about everything that Spurrier said,” said Wilson, the heart and soul of Tennessee’s 1998 national championship team.

Earl Brown and his wife, Judy, are some of the most dedicated Tennessee fans on the planet. Earl has been to 320 Tennessee football games in a row without missing one, a streak that goes back to 1996.

“There’s joy and relief,” Brown said. “There were a lot of years in there that we were the better team and didn’t win. I think this is the one that gets us back through that door of getting to where we all want to be again.”

The Vols (4-0) haven’t won more than eight games in the regular season since 2007, Fulmer’s next-to-last season.

Stephen Crutchfield hasn’t missed a Tennessee SEC game since 2007. He lives three blocks from Neyland Stadium in the Fort Sanders area just off campus. He said one of the reasons he moved there was to be closer to the Vols’ football cathedral.

“At the end of the day, people just want to win, and it doesn’t matter if it’s a defensive battle or the way we play now with a lot of offense,” Crutchfield said. “People don’t want to hear that you’re building anything or that you’re getting better or that you’re a class away. They just want to win, which makes a [win] like this so important.”

That’s why Rathburn, who graduated from Tennessee in 1987, didn’t mind making the eight-hour drive and a significant financial investment to be in Knoxville on Saturday. He paid $1,375 for three tickets in the upper deck and forked over $700 per night for a hotel room.

“This ranks up there with the ’98 Florida game with how crazy the place was,” Rathburn said. “I don’t remember it much louder. The Tennessee fans were hungry for this. There’s hope now, the kind of hope we haven’t had in a while. It’s amazing what Heupel has done in less than two years.”

Heupel’s demeanor is about as steady as it gets, and that steadiness has endeared him to his players. Tennessee fired previous coach Jeremy Pruitt after an internal investigation uncovered 18 Level 1 violations for impermissible recruiting benefits. Even with that NCAA cloud hovering, Heupel has steered the Vols to the No. 8 spot in the latest AP poll, their highest ranking since 2006.

“The guys play hard for Josh because he coaches unafraid,” said Scott Altizer, who returned as director of football relations last year after working for 20 years on Tennessee’s football staff beginning in 1994. “He preaches letting it all hang out and going out and having fun.”

Casey Clausen, the only Vols quarterback to have beaten Florida twice in his career (2001 and 2003), sees a version of Tennessee that he hasn’t seen in a while, a version that falls in line with Heupel’s go-for-broke, warp-speed offense.

“There’s a juice that’s back in the program, and for the younger generation of players, they don’t necessarily know about the past with Florida or anybody else, nor do they care or should they care,” said Clausen, who lives in California and still follows the Vols closely.

“Coach Heupel seems to have it back to, ‘It’s our team versus their team,’ and all the other noise doesn’t matter. You see that in the way this team plays, even when it doesn’t play its best football.

“The other thing is that he’s not playing with some of the same 4- and 5-star players a lot of the other SEC teams have, but he’s going to get there. You look at that offense and how fun it is to play in it, and why wouldn’t a big-time skill player want to come and play in that offense?”

This was a massive recruiting weekend for the Vols, as some of the top prospects on their board were in town.

Heupel made sure to practice what he preaches late Saturday night. Several of the former players, including Foster, were in the locker room after the game. And although nobody would say for sure, in the middle of that circle of 125 players dancing, Heupel might have been showing off a few moves of his own.

“If you can’t have fun in that environment, you can’t have fun anywhere,” said Heupel, who showcased his best vertical leap since his Oklahoma playing days and got in a few Tiger Woods-sized fist pumps after Jaylen Wright‘s 5-yard touchdown run gave his team a 38-21 lead midway through the fourth quarter.

Heupel typically has a large contingent of family in town for home games, and by the time he got home Saturday night after meeting with recruits and doing his TV show, he switched roles from coach to uncle with several nieces and nephews running around the house.

Finally, at the end of the night, he got to spend some quiet time with his wife, Dawn.

“Everybody had gone to bed, and we just looked at each other and said, ‘What a great day,'” Heupel said. “It was a huge moment for us as we continue to build this program and how much the players have invested. It’s really a lot of fun when you’re a part of the climb.”

But, as Heupel is quick to point out, the Vols are still in the early stages of that climb. After an open date, they play LSU on Oct. 8 and Alabama on Oct. 15, facing two of the past three national champions. That’s not to mention a game with No. 7 Kentucky on Oct. 29 and a trip to defending national champion Georgia on Nov. 5. The win over Florida was only the fifth Tennessee victory over Alabama, Florida or Georgia since the start of Fulmer’s final season in 2008, making the Vols 5-38 against those teams in that span.

That’s why Heupel was right back at the football complex at 7:30 Sunday morning meeting with recruits.

“There’s always another big game, another test right around the corner,” he said.

And while the Vols have more points through four games (194) than any Tennessee team since 1915 (202), Heupel isn’t about to get ahead of himself. The Vols made the kinds of mistakes in their first two games against nationally ranked opponents (Pittsburgh and Florida) that usually result in defeat — blocked punts, fumbled punts, fumbles in the red zone and not recovering onside kicks.

What’s more, Tennessee has struggled mightily against the pass on defense, both in getting to the quarterback and especially at covering receivers. The Vols are also precariously thin at some key positions, including the offensive line and defensive secondary.

“There are so many things we can do a lot better and will have to do better as we go forward, but I go back to the resiliency of our players,” Heupel said. “Obviously, we didn’t finish that game the way we needed to, and you could sense that from the crowd a little bit when [Florida] got the onside kick. But what I love about our group is that they just keep playing.”

One of the Heupels’ traditions after games is gathering all the family members in town for a picture on the field.

Heupel and his wife were looking through those pictures together late Saturday night.

“We’re all standing there together and the stadium is still checkerboarded behind us, and this is still probably 20 minutes after the game had ended,” he said. “That’s going to be a cool background to that picture for us.”

Come December, Heupel wouldn’t mind having a few more pictures like that to admire.

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‘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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'You don't want to have the same drip': How a Houston Christian receiver became a shoe artist to the stars

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.”

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MLB free agency tracker: 2025-26 offseason trades, moves

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MLB free agency tracker: 2025-26 offseason trades, moves

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

Passan’s offseason preview

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

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$400 million extension, blockbuster trade or let it ride? MLB insiders break down Tigers’ Tarik Skubal options

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0 million extension, blockbuster trade or let it ride? MLB insiders break down Tigers' Tarik Skubal options

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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