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  • Tom VanHaaren, ESPN Staff WriterJan 24, 2024, 09:39 PM ET

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    • ESPN staff writer
    • Joined ESPN in 2011
    • Graduated from Central Michigan

In his time as Michigan‘s head coach, Jim Harbaugh created media frenzies, dustups with coaches, viral moments with recruits and everything in between.

Hired in late 2014 to replace Brady Hoke as the Wolverines’ coach, Harbaugh wasted no time once in Ann Arbor ruffling feathers by poking at coaches for breaking rules and pushing the limits on what the NCAA would allow through satellite camps across the country.

He climbed trees, had sleepovers and made cakes for recruits to try to win them over. After three Big Ten titles, three College Football Playoff appearances and having delivered his alma mater its first national title since 1997, Harbaugh accepted the head-coaching job with the Los Angeles Chargers, sources told ESPN’s Adam Schefter.

Because he is departing the college football world, here is a look at some of his more memorable and viral moments since joining Michigan in 2014.

Feb. 7, 2015: Harbaugh had a commitment from ESPN 300 running back Mike Weber, a top prospect out of Detroit Cass Tech, in the 2015 class. Weber decommitted from the Wolverines in the middle of the fourth quarter of the team’s loss to Maryland in the 2014 season.

Harbaugh fought to get Weber back in the class, but the running back ultimately signed with Ohio State. Weber said at the time that Buckeyes running backs coach Stan Drayton was a big part of his commitment, but Drayton left to take the same position with the Chicago Bears the day after Weber signed his national letter of intent with Ohio State.

Harbaugh took the opportunity to seemingly tweet about the situation.

Weber stuck with Ohio State and played four seasons for the Buckeyes before he was selected by the Dallas Cowboys in the 2019 NFL draft.

March 3, 2015: Harbaugh is known to be a fan of TV star Judge Judy, even attending a taping of her show with his father, Jack.

So, he naturally took to Twitter to congratulate Judge Judy on a contract extension.

He has since played cards with the judge and has publicly talked about his admiration for her and the show.

“I’m a big fan of the ‘Judge Judy’ show,” Harbaugh told reporters at the 2013 NFL combine. “And when you lie in Judge Judy’s courtroom, it’s over, your credibility is completely lost, you stand no chance of winning that case. So, I learned that from her. It’s very powerful.”

March 14, 2015: The 2016 recruiting class is when Harbaugh really started to pull out all the stops on the recruiting trail. The staff put a ton of effort and creativity into recruiting ESPN 300 defensive lineman Boss Tagaloa, from California.

That included Harbaugh recreating a “promposal” poster that Tagaloa used to ask someone to prom. Harbaugh posed for a picture with a sign of his own that read, ‘UM will be sour without you, so let’s make it sweet. MICH?’

Tagaloa, however, ended up signing with UCLA.

April 24, 2015: The satellite camp idea was born. Harbaugh’s plan was to host football camps around the country, especially in SEC states.

One of the first big ideas that Harbaugh implemented ruffled the feathers of many other college coaches. Then-Alabama coach Nick Saban called the camps “ridiculous.” Harbaugh was accused of creating the camps as a recruiting tool, knowing that some conferences wouldn’t allow their programs to travel more than 50 miles to attend high school camps.

Harbaugh tweeted out an invitation to any other college coach who wanted to attend Michigan’s camps.

To get around the 50-mile rule for some schools, Harbaugh included an invitation for those coaches to come as guest speakers.

Then-ACC commissioner John Swofford said at the time that his conference would be in favor of a rule that would prohibit satellite camps across the country.

“We just don’t feel like it’s a healthy part of the recruiting process in college football,” Swofford said at the time. “We may have to ultimately reconsider it if the rules continue to allow it, because we’re not going to put ourselves in a competitive disadvantage in recruiting if we were to feel like we were disadvantaged, but our primary purpose right now is to try to gain support for a national rule that prohibits it.”

The NCAA first banned satellite camps, which triggered one of Harbaugh’s first public criticisms of the organization, but then rescinded the ban and allowed the camps to continue.

June 4, 2015: The tour of satellite camps, called the Summar Swarm, was announced in June. It consisted of nine locations, starting in Indianapolis, traveling to Alabama, Florida, Pennsylvania, Texas, California and eventually finishing back in Michigan. At the stops, Harbaugh would often wear jerseys representing local teams.

The tour spanned eight days and cost Michigan $211,948 in total, according to FOIA requests by MLive.

June 5, 2015: The Summer Swarm had already garnered attention from media and coaches, but Harbaugh wasted no time increasing visibility by taking his shirt off while playing a pickup game at one of the camps.

He kept his signature khakis on while playing a game of shirts and skins.

“I was like a pig in slop,” Harbaugh said at the camp. “Man, you guys are in shape. You’ve got a heart for football, a face for football, and I love being around you guys. That was a fun, fun day.”

June 25, 2015: Once the Swarm Tour was over, Harbaugh was back in Ann Arbor, entertaining recruits. He took tight end recruit Naseir Upshur and a few others out for ice cream, which Upshur documented on Twitter.

This was one of the more tame recruiting events, but given that Harbaugh was fresh off his cross-country antics, it once again made news.

Aug. 12, 2015: Prior to the start of his first season as Michigan coach, Harbaugh told reporters that after the wild tour, viral headlines and more publicity than Michigan had seen in quite some time, he and the team would be headed into “submarine” mode.

“We’re going into a submarine, and you won’t see us for a while,” Harbaugh said at the time. “You won’t hear from us, you won’t see us, we’ll be working. We’ll be in a bunker until we decide we’re not.”

No one from the team emerged from the submarine publicly until Aug. 27, when a few players talked to the media. Offensive lineman Kyle Kalis was one of the first players to surface.

“It was definitely an experience,” Kalis said. “One that I’ll tell my kids about when I’m older. It’s definitely been a camp unlike any we’ve had before, and it’s going to pay dividends for us down the road.”

November 2015: Harbaugh’s diet plan was revealed.

“I take a vitamin every day. It’s called a steak,” he said. “I truly believe the No. 1 natural steroid is sleep, and the No. 2 natural steroid is milk, whole milk. Three would be water. Four would be steak. It goes with everything.”

Harbaugh, who once appeared in a “Got Milk?” ad, later told Dan Patrick that he didn’t like having anything less than whole milk at the team’s dining hall.

“We refuse to drink the candy-ass skim milk or the 1%,” Harbaugh said. “We refuse. We won’t have any of that.”

In 2016, Harbaugh was photographed at an Ann Arbor steakhouse ready to enjoy his favorite meal.

Nov. 18, 2015: Harbaugh had done the promposal recreation for recruits, and members of his staff had written letters, but they moved on to baking birthday cakes for their prospects.

Jonathan Jones was the recipient of only a birthday cake tweet, so he didn’t actually get to eat the cake. It’s the thought that counts, though, and maybe Harbaugh and his staff enjoyed some of the cake in honor of Jones and his birthday.

They did it again for defensive lineman Jordan Elliott, making a cake that was supposed to look like Elliot’s home state of Texas. It worked only briefly, as Eliott committed to Michigan but eventually flipped to Texas.

Jan. 14, 2016: Following a 10-3 season, Harbaugh took the recruiting tactics to another level and had a sleepover at kicker Quinn Nordin’s house. The justification was that there was no limit as to how long an in-home visit could last.

So, in Harbaugh’s mind, if he stayed the night and stayed the rest of the day, it was all still one visit.

News of the sleepover spread quickly, and Nordin’s neighbors decided to troll Harbaugh with a giant sign displaying the score of that year’s Michigan-Michigan State game, which the Spartans had won.

Harbaugh went to Nordin’s high school the next morning and eventually rode in the car with him to Ann Arbor for a visit.

Jan. 19, 2016: Harbaugh then traveled to the West Coast to continue recruiting Tagaloa, who got the promposal recreation. This time, Harbaugh attended class with the defensive tackle at his high school.

Jan. 19, 2016: Harbaugh stayed in California to recruit cornerback David Long.

They were outside of Long’s house, playing catch with Long’s siblings. Before they knew it, Harbaugh was climbing a tree.

“My little sister asked if he could climb the tree,” Long said at the time. “He was just trying to fulfill her request. He ended up putting my little brother up instead, because he never actually made it up.”

There was a picture that circulated online showing Harbaugh climbing the tree while wearing his khaki pants.

Jan. 20, 2016: The sleepover with Nordin was such a success that Harbaugh decided to do it again, this time with defensive end Connor Murphy.

Harbaugh had history with the Murphy family, because he recruited Connor’s older brother, Trent, to Stanford. Harbaugh babysat for Connor once when he was younger, but this time he was there recruiting the younger Murphy.

Feb. 24, 2016: The satellite camps created quite the dust-up among other coaches who weren’t happy about the decision to allow the camps to continue.

“[Michigan is] obviously trying to gain a competitive advantage, and obviously that’s their right,” Georgia coach Kirby Smart said at the time. “But I think the NCAA in due time will have to step in and keep it from getting out of hand.”

That comment seemed pretty tame, but Harbaugh took offense to it and tweeted back at Smart.

Not much came from the exchange, but Harbaugh wasn’t done calling out opposing coaches.

March 3, 2016: Harbaugh and his staff were getting ready for their camp at IMG Academy in Florida, when then Arkansas coach Bret Bielema said he would attend, along with Michigan State coach Mark Dantonio.

Dantonio joked with Bielema that they could meet in Florida for lunch, which caused then-Tennessee coach Butch Jones to say he, too, would meet them for lunch in Florida.

That didn’t sit well with Harbaugh, who subtweeted Jones by calling him his “Rocky Top colleague.”

April 2, 2016: This is when Harbaugh began going on stage with rappers. That included joining Lil Dicky, who was performing in Ann Arbor, for a rendition of the national anthem.

April 13, 2016: Just 11 days after going on stage with Lil Dicky, Harbaugh spent time with rap group Migos before their concert in Detroit.

The group asked Harbaugh to come on stage and dab with them, so they naturally had to ice him out with jewelry before he made his appearance.

Harbaugh did go on stage and was doused with water while dancing during the concert.

Harbaugh would later invite the group back to Ann Arbor.

May 31, 2016: Harbaugh was back to throwing shade at opposing coaches, this time at Saban.

At SEC meetings, Saban had talked about despising satellite camps and said college football was moving toward the wild, wild west. His comments drew the ire of Harbaugh and resulted in his tweet.

Saban later fired back at Harbaugh through reporters.

“I don’t really care what he thinks or tweets,” Saban said. “I say what I think is best for college football and the players.”

June 9, 2016: Harbaugh had built a relationship with the staff and administration at Paramus Catholic High School through recruiting Paramus players Jabrill Peppers and Rashan Gary.

The plan was for the coaches to come to Paramus Catholic for a satellite camp, but the NCAA put a temporary ban on the camps at the time. That led to Harbaugh coming to the school and giving the commencement speech for the graduating class.

The coaches were recruiting linebacker Drew Singleton and a few other players from the team, so it gave Harbaugh a chance to have a presence at the school.

July 18, 2016: Harbaugh continued appearing on the rap scene, this time with artist Bailey in a song called, “Who’s got it better than us?” That is, of course, Harbaugh’s signature saying.

July 14, 2016: Harbaugh ended the camp tour early, because there was fear of the Zika virus in American Samoa, where a camp was supposed to be held. He instead stayed in California and took a trip to Disneyland, where he ran into talk show host Jerry Springer.

Oct. 15, 2016: Recruiting in the San Francisco area, Harbaugh held the down marker on a chain gang at a high school game.

Nov. 12, 2016: Speaking of random, Harbaugh went on a radio show and spoke about his admiration for SpongeBob SquarePants.

“I love his attitude,” Harbaugh said at the time. “He attacks each day with an enthusiasm unknown to mankind! I’ve kind of modeled my behavior after him. We all should. What a great employee he is. He’s a go-getter. He’s always got a bounce to his step. He’s got pizazz. He puts his heart and soul into making those Krabby Patties. I think he’s awesome.”

April 26, 2017: Harbaugh started a tradition of taking the team to meaningful places during the offseason.

In 2017, he took the team to Italy, where Harbaugh had the chance to meet the pope. Of course, upon meeting Pope Francis, Harbaugh gave him a Michigan helmet and Jordan Brand shoes.

If you were hoping the pontiff would make an appearance while wearing the Jordans, it hasn’t happened yet.

April 28, 2017: While in Italy, Harbaugh did an impression of Maximus from the movie “Gladiator.”

And sang some opera for reporters.

Sept. 30, 2017: During a bye week, Harbaugh went to Michigan’s Water Carnival and participated in some of the platform diving. He, of course, did it in khakis.

He tried multiple times in what was determined to be a cannonball contest.

July 19, 2018: “Car and Driver” magazine went to Ann Arbor to do a video segment with Harbaugh and a Dodge Charger. Harbaugh drove to his childhood house, and then drove the car into the Big House and did doughnuts on the turf.

July 30, 2018: In a story in Bleacher Report, Harbaugh was quoted as telling quarterback Wilton Speight to avoid chicken “because it’s a nervous bird.”

Aug. 6, 2020: During a conference call among Big Ten coaches, Harbaugh reportedly interrupted Ohio State coach Ryan Day and asked him about a photo that showed then assistant coach Al Washington coaching the linebackers during a time on the calendar when it wasn’t permitted.

Day reportedly responded by telling Harbaugh to worry about his team. After the call, Bucknuts reported that Day told his team that Michigan should hope for a mercy rule, because they’re going to, “hang 100 on them.”

Sep. 15, 2020: This is the last time that Harbaugh tweeted, perhaps ending an epic run of one of the great Twitter beefers.

Nov. 28, 2021: After Day said Ohio State was going to hang 100 points on Michigan, the Wolverines beat Ohio State 42-27. Harbaugh wasted no time when asked in his postgame press conference what he thought of Ohio State’s trash-talking in recent years.

“Sometimes there are people standing on third base that think they hit a triple,” Harbaugh said at the time. “But they didn’t.”

Harbaugh eventually explained on 97.1 The Ticket in Detroit that it was a shot at Day.

“It was definitely a counterpunch by me, to the comment that they were going to hang 100 on us, etcetera,” Harbaugh said on the radio. “Kind of like Sugar Ray Robinson.”

Jan. 20, 2022: While Harbaugh hasn’t been on social media, it doesn’t mean he hasn’t gone viral. While recruiting players at Jesuit High School in Tampa, Florida, he decided to do squats in the weight room.

Dec. 11, 2022: In-home visits with Harbaugh have already produced sleepovers and tree-climbing escapades.

In a seemingly tamer moment, Harbaugh helped wash the dishes at receiver Semaj Morgan’s house on a visit.

Feb. 22, 2023: Picture yourself driving on a road at night, when you come across a large tree blocking your way. Now imagine you look out your windshield to see Jim Harbaugh trying to move the tree in front of you.

That is exactly what happened to one driver near Ann Arbor, as Harbaugh made the news for helping a police officer move a tree out of the road. The ordeal was caught on the police camera and footage was later shared online.

Sep. 9, 2023: While serving a three-game suspension for NCAA recruiting violations, Harbaugh was back working with the referee crew.

Sep. 30, 2023: Defensive tackle Kenneth Grant intercepted a pass against Nebraska, which was quite the feat for a 6-foot-3, 339-pound lineman. After the game was over, when everyone was in the locker room, Harbaugh decided that the whole team should sing the song, “For He’s a Jolly Good Fellow,” to Grant.

The song somehow stuck with the team and they sang it after every game this season.

Nov. 6, 2023: Pro wrestling icon Ric Flair and Harbaugh became friends when Harbaugh played for the Chicago Bears and have spent time together ever since.

Flair showed up to Ann Arbor for a visit in November and exited the building without his signature, “Woo.”

Nov. 13, 2023: Harbaugh sounded as though he was losing his voice, but insisted he wasn’t sick.

Instead, he insisted that he is the “iron wall that viruses bash against” and he’ll do “push-ups and eat an apple” to get better.

Nov. 20, 2023: In one of his final odd statements as Michigan coach, Harbaugh quoted Ted Lasso.

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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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November 20, 2025

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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

  • Max OlsonNov 20, 2025, 07:00 AM ET

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    • Covers the Big 12
    • Joined ESPN in 2012
    • Graduate of the University of Nebraska

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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November 20, 2025

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

Nov 19, 2025, 06:00 AM ET

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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November 20, 2025

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

  • Kiley McDanielNov 20, 2025, 07:00 AM ET

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    • ESPN MLB Insider
    • Kiley McDaniel covers MLB prospects, the MLB Draft and more, including trades and free agency.
    • Has worked for three MLB teams.
      • Co-author of Author of ‘Future Value’

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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