The Shady Side Of Bill Belichick

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Most professional coaches fall into one of two main categories. There are the brave, unimpeachable leaders admired by their athletes and their team's fans as victory-minded strategists on par with military heroes. (Think Phil Jackson, Gregg Popovich, or Vince Lombardi.) Then there are the high-strung guys, the ones who yell and scream and take their jobs way too seriously — Bobby Knight, for example, or Mike Ditka, a tough former player and even tougher coach who wasn't nicknamed "Iron Mike" for nothing.

And then there's Bill Belichick. The longtime New England Patriots head coach must be doing something right — he guided the team to six Super Bowls since taking the reins in 2000, while also claiming two previous Super Bowl wins for the New York Giants while he served as defensive coordinator. After several seasons without making it to the big game, Belichik parted ways with the Patriots in January 2024.

Through it all, he's been a hard nut to crack. The guy rarely smiles and keeps a low profile, for good reason. Let's shed some light on some of the darker aspects of his life by delving into the shady side of Bill Belichick.

New York Jets fans probably harbor a special kind of animosity for Bill Belichick. Not only have the Patriots beat the Jets to win the AFC East 17 times in the Belichick era, but there's also an element of "it could have been us" lingering in the air.

In early 2000, Bill Parcells resigned as head coach of the Jets, but he had plans in place for assistant coach Belichick to take over. Belichick was announced as the Jets' new coach, and the next day the team held an introductory press conference. But instead of taking the wheel, Belichick resigned to the surprise of everyone, including the New York Jets organization.

"Due to the various uncertainties surrounding my position as it relates to the team's new ownership," Belichick said at a press conference. "I've decided to resign as the head coach of the New York Jets." He reportedly penned his letter of resignation on a napkin. His reasons were cryptic, but direct: "I've been in situations ... where I was the head coach of a team in transition," he said at his hello-goodbye press junket. "Frankly it wasn't a really good experience for me or for them."

Bill Belichick's weird rivalry with the New York Jets flared up again during a Jets-Patriots game in September 2007, when NFL security caught a guy on the Jets' sideline area recording the team with a video camera. That dude turned out to be Matt Estrella, New England's video assistant, and the NFL determined he was taping the Jets' defensive coaches' secret signals to players so that Belichick and the Patriots could decode them.

NFL commissioner Roger Goodell fined Belichick the league-maximum penalty of $500,000 (more than 10% of his salary for the year) and took away one of the team's future first-round draft picks. "This episode represents a calculated and deliberate attempt to avoid longstanding rules designed to encourage fair play and promote honest competition on the playing field," Goodell wrote in a scorched-earth letter sent to the Patriots (via the team's website).

Belichick ultimately issued an apology for what had taken place. "Although it remains a league matter," he said in a statement, "I want to apologize to everyone who has been affected, most of all ownership, staff and players."

If anything has been established about Bill Belichick, it's that he will do anything for a win — especially if it's in a game against those pesky New York Jets. Before the teams played in December 2017 on the Patriots' home turf in Foxborough, Massachusetts, Belichick had thermometers placed in the tunnel from which the Jets would emerge onto the field. Why?

Psychological warfare. The Patriots have historically played well in frigid temperatures, and Belichick reportedly wanted to disarm, discombobulate, and psych out Jets players not used to the cold by telling them exactly how cold it was (15 degrees Fahrenheit with a wind chill of –4).

Adding insult to injury, it was the last game of the season, and the already playoff-bound Patriots were looking to secure home-field advantage in the playoffs. The Jets, meanwhile, had amassed a lowly 5-10 record. Final score: Patriots 26, Jets 6.

The results of the AFC Championship Game in 2015 weren't necessarily shocking. The New England Patriots easily defeated the Indianapolis Colts 45 to 7, but something was amiss. The NFL launched an investigation to determine if the Patriots had intentionally under-inflated the footballs used during the championship game. Why would they do that? It's apparently a low-key way to make them easier to throw. Colts linebacker D'Qwell Jackson reportedly intercepted a pass from quarterback Tom Brady, and the equipment manager who grabbed the ball after the play thought it felt too soft.

The sometimes-shady Brady denied any impropriety, although when league officials examined the 12 game balls controlled by the Patriots, 11 of them were significantly softer than they should have been. The NFL suspended Brady for four games, along with two equipment managers believed to have done the actual deflating, and docked the team $1 million and a couple of draft picks.

While Bill Belichick denied any connection with "Deflategate" and was never punished for any wrongdoing, many have questioned how something so significant could happen without the authoritarian coach not knowing about it, particularly one who'd been caught cheating before.

Sure, watching elite athletes slam into each other is a lot of fun, but the revelations about CTE, chronic traumatic encephalopathy, make the sport increasingly controversial for everyone involved. CTE is a medical condition marked by degeneration of brain tissue brought on by repetitive brain trauma, including the kind of trauma a player might endure playing football.

After he was sent to prison for murder in 2017, former New England Patriots tight end Aaron Hernandez died by suicide. His autopsy uncovered a significant case of CTE. On the same day that the autopsy results went public, Hernandez's fiancée sued the NFL and the New England Patriots, claiming in documents obtained by USA Today that both entities "were fully aware of the damage that could be inflicted from repetitive impact injuries and failed to disclose, treat, or protect" Hernandez.

When a reporter asked Bill Belichick what the Patriots do to warn or protect players against CTE, the coach played dumb and dodged the question. "I'm not a doctor. I'm not a trainer. I'm a coach," he said during a press conference. "So, the medical department, they handle the medical part of it. I don't do that." It's hard to believe that one of the most experienced and successful coaches in the game could be so clueless or disinterested about such a serious — and life-threatening — topic.

Despite his steely demeanor and utmost devotion to football above all other things, Bill Belichick has opened his heart on more than one occasion. In 1977, he married the former Debby Clarke. Their partnership was long and fruitful, spawning three kids and the Bill and Debby Belichick Foundation, a homeless assistance charity. Then it all fell apart — they separated in 2004 and divorced in 2006.

But Belichick learned to love again, coupling up in 2007 with Linda Holliday, a boutique owner and television lifestyle correspondent he reportedly met at a Florida nightclub. She's also a solid decade younger than Belichick.

Okay, okay. Love is love and who are we to judge based on the number of birthday candles on the cake? Valid point. Besides, the coach seems very happy. Though he keeps pretty much everything close to the vest, Holliday is quite active on social media, and she frequently posted pictures of herself and her dude having a good time. How good? Holliday can actually get Belichick to smile — a rarity. How rare? Over the course of nine seasons with the Patriots, wide receiver Julian Edelman claims to have seen Belichick smile just twice. Sadly, the couple went on to split in 2023.

Somewhere in the midst of his crumbling marriage to Debby Clarke and budding relationship with Linda Holliday, Bill Belichick reportedly had another flame. That shocking tidbit of gossip was revealed in, of all places, the New Jersey court system.

During the 2007 resolution of financial agreements in the otherwise ho-hum divorce proceedings between Vincent and Sharon Shenocca, it came out that Sharon had a large and secret source of income. That income was allegedly from Belichick. For the year and a half leading up to the divorce hearings, Belichick had reportedly been Sharon's "sugar daddy." He supposedly bought her a fancy Brooklyn townhouse, paid for her summer rental on the always classy Jersey Shore, sent her to Disney World on a private jet, and provided her with about $3,000 a month.

Get this: Among the things Sharon supposedly purchased with Belichick's money were ... wait for it ... New York Giants tickets — as in the football team that defeated the Patriots in the 2008 Super Bowl. Who's the shady one now?

Bill Belichick's relationship with girlfriend Linda Holliday lasted a solid 16 years before the two broke it off in the fall of 2023, with a source confirming to People that the "relationship ran its course." Less than a year later, Belichick revealed he had a new girlfriend: Jordon Hudson. Like his previous relationship, there was a significant age gap between the two, but far more dramatic than the decade that separated him and Holliday: Hudson is 48 years younger than him, just being 23 years old when she began dating the 72-year-old Belichick.

Belichick reportedly met Hudson — who was then a college student and aspiring beauty pageant contestant — in 2021 when they were seated next to each other on a flight and engaged in a conversation about some schoolwork she was doing. They kept in touch, and when he split from Holliday, their relationship turned romantic.

It was later revealed that there was bad blood between Holliday and Hudson when the latter turned up — sans Belichick — at a Nantucket Christmas party where Holliday's daughters were DJing. Holliday was reportedly furious to see her ex's new partner and confronted her in what was characterized as a tense encounter. "Jordon was asked to leave by a group of people, but ultimately I think it was Linda who asked for her to leave," a source told People. Another source recalled, "It was very uncomfortable. There was a lot being exchanged between them. It was very aggressive behavior."

Following Bill Belichick's exit from the New England Patriots in early 2024, there was much speculation regarding which NFL team he would coach next. As it turned out, Belichick's next job wasn't with the NFL. Instead, he was hired as head coach of the University of North Carolina's football team.

Controversy arose, however, when reports emerged that he insisted that all of his UNC email correspondence be CC'd to Jordon Hudson. That certainly raised questions, but ESPN's Pablo Torre offered what he believed to be the answer during an episode of his podcast, "Pablo Torre Finds Out." "She has represented herself essentially as his de facto agent," Torres claimed. "The person who you need to go through to book Belichick for a Super Bowl commercial."

When the controversy refused to die down, Belichick finally addressed it, explaining why she was being CC'd. While appearing on "The Pivot" podcast, Belichick denied that Hudson had any formal role with UNC, but did kind of confirm that she was fielding offers for him. "It would be personal opportunities," he said. "It could be a speaking thing, it could be an appearance on this, talk about that ... and she would kind of help organize that."

While Bill Belichick may have downplayed Jordon Hudson's involvement in his career, the truth emerged when he sat down for an interview with "CBS Mornings" to promote his new book, "The Art of Winning: Lessons From My Life in Football." During the exchange, Belichick — bizarrely attired in a ratty sweatshirt with a prominent rip near the collar — was asked about how he and Hudson met. At that point, Hudson abruptly interrupted the interview. "We're not talking about this," she declared.

According to the outlet, that wasn't the only time that she butted in to slam the brakes on her beau's interview; she reportedly did the same thing several other times, but CBS decided to keep that one interruption in the edited version that made it to air. Meanwhile, TMZ reported that things became so tense that Hudson stormed off at one point, delaying the interview by a half-hour. Suddenly, Belichick was neck deep in a PR debacle, shifting the focus from his book and new UNC coaching job, and placing it solely on his 24-year-old girlfriend. Former Patriots quarterback Cam Newton skewered his one-time coach for doing exactly the opposite of what he's told players. "He's always led with this: 'Do not be a distraction,'" Newton said on his podcast, "4th&1 with Cam Newton," pointing out that Belichick was now ignoring that very edict.

In his subsequent interview on "The Pivot" podcast, Belichick attempted some damage control by explaining his girlfriend's role in his professional life. "But, really, what she does helps me spend my time on football, and that's what's important to me," he said.

While Bill Belichick contended that girlfriend Jordon Hudson played an important role by helping him with his various media and personal responsibilities so he could focus on football, another report emerged claiming that she cost him a lucrative deal. The New York Times reported that NFL Flims was keen on featuring Belichick's first season with the University of North Carolina in its HBO documentary series, "Hard Knocks." A deal was reportedly struck, but mere days before an official announcement was set to be made, Hudson issued a demand for final approval, while also insisting on being issued a partial ownership stake in the show. NFL Films balked and scrapped the whole thing.

In addition to cancelling all the attention that would have gone to Belichick and the North Carolina Tar Heels, Hudson's antics wound up costing her boyfriend a reported $200,000. While a press release and promotional artwork were reportedly all ready to go, Belichick denied that Hudson had anything to do with the deal falling apart. "We're not training camp. We're just not," Belichick told "The Pivot." "The drama of training camp and who's gonna get cut and all that. We're a season, and they don't want that ... 'Hard Knocks' just didn't fit for us. That's the bottom line."

In April 2025, Jordon Hudson revealed that she'd been fibbing about her age, yet another weird thing about Bill Belichick and Hudson's relationship. She had only just turned 24, and was a mere 23 when she first began dating her "old bae," which is what she called Belichick him a May 2025 Instagram post. Not long after that, rumors began to swirl that Belichick had popped the question, and the two had gotten engaged. In fact, that New York Times feature claimed that Hudson had told at least one acquaintance that she was now his fiancée. "Ms. Hudson has told at least one person that she and Mr. Belichick are engaged to be married," they reported.

According to ESPN's Pablo Torre, members of Belichick's family have been privately expressing grave reservations about his relationship with Hudson. "Bill Belichick's family is extraordinarily concerned about what has transpired," Torre said during his podcast. "One Belichick family source told me, 'There is deep worry for how detrimental Jordon can be for not just North Carolina but Bill's legacy, reputation — everything he has built and worked for over decades.'"

Bill Belichick's new status as tabloid fixture did not go unnoticed by his colleagues in the world of sports. That was particularly true with Upton Bell, who was once general manager of the New England Patriots, back in the early 1970s. Speaking with The New York Times, Bell offered a scathing critique of reports that Belichick was being controlled by his 24-year-old girlfriend, Jordon Hudson. "I think it's ironic that a man who really controlled everything — and I mean everything — now is being controlled by some other person," Bell said.

However, Bell deviated from popular opinion by shifting the blame for the situation from Hudson to Belichick himself. "You can't just point at the woman here and say, 'She is being controlling,'" he said, explaining that Belichick had clearly — and willingly — turned over the keys to Hudson. "That only happens if you let yourself be controlled," he added.