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IN HIS EIGHT seasons in the big leagues, New York Mets outfielder Terrance Gore has never hit a home run. He has just one career RBI. But he does lead baseball in one very important category: World Series rings.

With three, Gore is tied with Madison Bumgarner for the most rings among active players in the majors, and has more than the entire Mets clubhouse combined. With his team among the National League favorites heading into the 2022 postseason, the journeyman pinch-running specialist is looking to add to his collection — with a lofty goal in mind.

“I’m trying to catch Tom Brady,” Gore says. “I like my odds.”

Brady, of course, owns seven rings as a future Hall of Fame quarterback for the New England Patriots and Tampa Bay Buccaneers, but Gore — a 31-year-old speedster known only to the most die-hard baseball fans — finds himself nearly halfway there.

“I wish I had that many World Series rings,” All-Star Mets shortstop Francisco Lindor says. “I’m a little envious.”

There’s a catch: Gore has never actually played in a World Series game. Since the Kansas City Royals drafted him in the 20th round in 2011, Gore has put together one of the most unique careers in sports history, a playoff base stealer for hire, often added to rosters in late September or October as one of the game’s fastest runners, deployed in the late innings of close games. He’s been a key contributor along the way, but has yet to appear in the Fall Classic.

In June, Gore joined the Mets, his fourth team. In eight games, Gore does not have a hit in three at-bats, but has stolen three bases and has not been caught once. The Mets hope, come October, that Gore can help the team create runs on the basepaths while providing some of the luck he’s brought the past two seasons to the Los Angeles Dodgers and Atlanta Braves, plus the Royals in 2015, all of whom won the World Series with Gore on their playoff rosters.

“Everyone knows when I go out there what I’m doing,” Gore says. “It’s like cat and mouse. Here we go. There’s no hiding.”


BEFORE GORE BECAME an October good luck charm, he almost quit baseball.

In 2014, Gore was frustrated with his progress. As a kid, Gore had envisioned a career like Ichiro Suzuki’s or Juan Pierre’s. But in his fourth year in the Royals organization, he wasn’t making much of a mark as an everyday player at High-A Wilmington, hitting .218/.284/.258 with no home runs and 36 stolen bases in 89 games. As he struggled in professional baseball, his ambitions shrunk, and he found himself dreaming not of MLB success, but of simply making a living, in the minors.

With a child on the way, though, Gore also considered hanging up his spikes altogether.

“I didn’t have a plan,” Gore says. “I knew I needed to do whatever it took to provide for the family.”

Gore didn’t see a path to the big leagues. He wasn’t developing as an all-around player and as his teammates got younger and younger, it felt like his window was closing. Gore routinely talked to his agent, Jay Witasik, who had pitched 12 years in the major leagues, about leaving the sport.

As he wavered, Gore grabbed dinner with former Royals slugger Mike Sweeney, who was working with the team as a special assistant. Sweeney pushed back on Gore’s plans to leave baseball, imploring Gore to stick with it for another year — an opportunity might be coming soon.

That opportunity came a few months later in early August when Gore got the call to join the Triple-A Omaha Chasers, where the Royals wanted him to pinch run and steal bases against a higher level of competition. The plan was for Gore to come up to the big leagues and be a pinch runner for the team’s postseason run.

“I had zero idea,” Gore says. “I stole bases down there, but I just did it because it was something I was good at.”

Just a month later, Gore made his major league debut against Cleveland, pinch running for the Royals just 26 days after his last game in Single-A.

“It was like he was shot out of a cannon every time he took off,” says ex-major leaguer Rusty Kuntz, then the Royals’ first base coach. “I grew up with Vince Coleman, Rickey Henderson, Tim Raines, the guys in the Hall of Fame with that kind of speed, and this guy is right there.”

Players like Salvador Perez, Jarrod Dyson, Eric Hosmer and Mike Moustakas took Gore under their wing, a 23-year old who nearly quit baseball now playing high-pressure games in October.

“I was just hoping and praying to God, do not fall on your face in the middle of the base path,” Gore says. “I am notorious for tripping and I’ve come really close to stumbling, so I was like, do not do this on TV.”

While the Royals did not win the World Series in 2014, they raised the trophy in 2015. That year, Gore stole a base in Game 4 of the ALDS against the Houston Astros after spending the majority of the season in Double-A. Gore says he does not remember much of his first two postseasons because he blacked out from the pressure. Still, the thrill of success in the majors got him hooked.

“There was no turning back. Once you get a taste of it, it’s almost like a shark,” Gore says. “You get the taste of that blood and you’re like oh man, I want to keep going.”


SINCE THEN, GORE has accepted his role as a premier pinch runner and shifted his training strategy accordingly, de-emphasizing hitting to focus on improving his speed through sprints and flexibility while working on reading pitchers on the mound. Perhaps the only comparable career in MLB history is that of Herb Washington, a four-time All-American sprinter at Michigan State who played two years for the Oakland Athletics, stealing 31 bases without a single at-bat and winning a championship in 1974. Gore’s legs alone got him his first World Series ring, and leaning all the way in like Washington seemed his best course forward.

“I’m just going to ride this wave,” Gore says. “Be really freaking good at it and see where it takes me.”

In 2018, the Royals shipped Gore to the Chicago Cubs, who put him on the postseason roster for the wild-card game, where Gore stole a base and scored a run in a Cubs loss to the Colorado Rockies. He returned to the Royals in 2019, getting his most extended time in the majors to date, playing 37 games while hitting .275/.362/.353 and stealing 13 bases before being sent to the New York Yankees and finding himself back in the minor leagues.

Ahead of the 2020 season, Gore signed with the Dodgers, for whom he appeared in two regular-season games before being added to the 28-man roster for the wild-card game and the NLDS. Dodgers manager Dave Roberts said it would “be pretty costly” to not have Gore on the playoff roster, despite the outfielder not appearing in any games. And when the Dodgers won the World Series, Gore got his second championship ring.

Gore next signed with the Braves, who did not call him up during the 2021 regular season. But when Atlanta reached the NLDS, Gore joined the roster, making one appearance as a pinch runner. And when the Braves won the World Series, Gore got his third championship ring, his second in a row.

Noticing a trend in how teams used him, Gore and Witasik came up with a different free agent strategy for 2022, deciding not to sign with a team until halfway through the season. The approach allowed Gore to gauge which interested teams had a shot at making the postseason and where he could maximize his impact. They knew the same teams interested in his speed in February would be just as interested in June ahead of a postseason run.

“For 99.9 percent of how things work, you get the player the deal and they develop throughout the season. But with Terrance, he’s not that guy,” Witasik says. “He’s a once-in-a-generation type guy with his speed and skill set.”

Gore feels the pressure every time he takes the field, knowing he’ll be called onto the basepaths in key situations. To prepare for these moments, he reads scouting reports that break down the pickoff moves and windup timing for each pitcher on the opposing team, studying video of how each of them holds runners on base, examining everything from their feet to their eyes.

“I’ve embraced it now. It’s got me three World Series rings so why not just keep on chugging along and see how far I can go.”

He might never win as many rings as Tom Brady, but with another on the line this October, he’s feeling pretty ambitious. If he wins a fourth ring, and his third straight?

“Put me in the Hall of Fame,” Gore says with a laugh.

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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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