Beyond His $41 Million Contract Extension How NY Giants Wide Receiver Sterling Shepard Is Living The Dream

Sterling Shepard
Jacket: Michael Kors Pants: Theory Shirt: Tom Ford Watch: Zenith

Photo Credit: Scott McDermott

Photography: Scott McDermott
Styling: Dex Robinson STYLING DEX ROBINSON
Grooming: Q

Shot on location at 225 West 17th Street, Penthouse, New York, NY 10011

In the cinematic version of Sterling Shepard’s life, a disembodied voice whispers, “If you believe it, they will come.” So he does, and then his dreams become reality.

Actually, that kind of did happen, minus the ghostly advice. While he was negotiating his recent $41 million contract extension with the New York Giants, the 26-year-old athlete invoked the power of manifestation. Which is why he purchased a permanent home in Montclair, New Jersey… a week before said contract was officially offered.

His palatable relief has nothing to do with a real estate investment that could have gone wrong and everything to do with how very much he wanted to continue playing for the team that gave him his start in the NFL. “It’s honestly a weight lifted off my shoulders,” he says on an exhale. “It’s a great feeling to be able to provide for my family and be in touch with this great city for another five years.”

And yes, maybe he anticipated the outcome, but there’s knowing and there’s knowing. Either way, he knew enough to put down roots with confidence—because fortune favors the bold. “I kind of sensed that the contract was coming because of the way the negotiations were heading, but [to be honest], I’ve always seen this happening for myself,” he notes. “I think there’s power in visualization. If you visualize something, it can come true, especially if you put in the work. And I definitely put in the work to get that extension.”

Sterling Shepard
SWEATSHIRT, SWEATPANTS, SOCKS & T-SHIRT: Thom Browne (Available at Je rey New York)

Photo Credit: Scott McDermott

This he can also state with confidence. Immediately after being drafted by the team in 2016 (as a second round, 40th overall pick), Shepard had one of the best rookie seasons by a pass-catcher in Giants history, starting all 16 regular-season games as well as in the NFC Wild Card Game. He also became the first player in the team’s history to score a touchdown and have more than 100 receiving yards in a game. Other career highlights include 190 total catches for 2,286 yards, 14 touchdowns and four career 100-yard games. And now, he seems unstoppable:

He’s been dubbed one of the top 20 players in the league, no doubt because he’s coming off career highs in yards (872) and catches (66).
One might say that he deserves this adjunct, that he’s proven why he’s worthy of staying and playing in The City That Never Sleeps for another five years—in addition to the four-year extension, he has one year remaining on his initial rookie contract. He’s also earned his place as the team’s longest-tenured wideout. In fact, he’s the only wide receiver who’s been on the team longer than a solitary season.

The extension had certainly been his most immediate goal. “When you play in the NFL, this is what you look forward to,” he maintains.
“A lot of guys try to get at least that second contract, if not a third.”

But Shepard isn’t going to focus on that third contract… yet. He wants to let the excitement of his second soak in first and prove that he’s deserving of the Giants’ faith. “I was able to get that extension because of the way that I work,” he notes. “I’m going to be the No. 1 wide receiver this year, so I’m trying to set the standard for the rest of the guys. Plus, you get that extension, and it shows the trust [the team] has in you, and you just want to prove the reason why you’re here for an extended amount of time.”

Plus, why should he think about the future when the present is so perfect? In football, as in life, it’s anybody’s game… and anything can happen (including that he had to sit out five games back in 2017 for migraine issues), so he plans on enjoying the here and now. “I try not to look too far into the future; I’m just taking life one day at a time,” he says. “With this profession, you never know what could happen, so I’m just trying to make the best of every moment.”

Sterling Shepard
JACKET, PANTS & SNEAKERS: Ermenegildo Zegna WATCH: Zenith

Photo Credit: Scott McDermott

He does that on the daily by building rapport and relationships with his teammates, whom he truly considers to be family, and goes the extra mile to welcome new players, including 10-year veteran Golden Tate and Arizona Cardinals transplants Antoine Bethea and Markus Golden into the Giants fold. He and the squad—minus shining star Odell Beckham Jr., who was traded to the Cleveland Browns—recently started their offseason OTAs (organized team activities) back at the Meadowlands Sports Complex in East Rutherford, New Jersey. “I’ve been working hard to build camaraderie with the new teammates and pushing myself to be the best I can be,” he says.

He’s already better than the most important football player in his life: his father. Derrick Shepard was also a wide receiver in the NFL—he played for the Washington Redskins, New Orleans Saints and Dallas Cowboys for a total of four years before retiring in 1992. He had a heart attack in 1999 age 35, and passed away when Sterling was just 6 years old.

“[My father’s NFL career] was a huge influence,” he admits. “It’s actually kind of funny, because I don’t know what my love for the game would look like with him here. I look at my cousin and uncle [former University of Oklahoma Sooners QB Darrell Shepard], and my uncle was really hard on him and pushed him away from the game. My dad was also hard on me at a young age.”

But because he never had the chance to find out, he started—and continued—on his dad’s path. Growing up as a little boy in Oklahoma City, his mother would make him football cakes for every single birthday. Cake and success are similar to the athlete: Both are equally as sweet. “[That cake] and to play football was all I ever wanted,” he recalls. “That’s all that has ever been in my head, that this is what I want to do. Anytime in grade school anyone asked me what I wanted to be, I’d say, ‘An NFL football player.’ That’s what every kid would say, but I knew in my heart that that’s what I wanted to do, and I was going to make it happen no matter what. It’s always been that way for me.”

Sterling Shepard
SHIRT: Lanvin
PANTS: ALYX SNEAKERS: Veja
WATCH: Zenith

Photo Credit: Scott McDermott

He also wanted to discover a piece of the father that he lost. “I love the game and wanted to follow in his footsteps,” he confides. “When I was in college [at the University of Oklahoma], I always wanted to wear his number. My head coach actually coached with my dad, so he knew the importance to me, and I wore my dad’s number throughout college. When I got to the NFL, they actually held my dad’s number because they knew how important it was for me, too. Following in his footsteps has always been my No. 1 goal.”

And there’s another reason. “I always wanted to be better than him,” Shepard confesses. “My mom would always say, ‘You’re better than your dad,’ and I’d say, ‘I don’t know, I don’t know.’ But now I can say, ‘I think I got him!’”

If Shepard, now 26, could speak to his 25-year-old self, he’d tell him this: “Buddy, in just one year, all of your dreams are about to come true.” In the span of one year, he became a major player, a husband and a dad. And the latter two, at least, he owes it to former teammate Victor Cruz. It was at Cruz’s 2016 birthday party that he met wife, Chanel Iman, after all.

Shepard was mere months into his rookie season with the Giants when he attended Cruz’s 30th festivities at the Hunt & Fish Club in NYC and spied Iman, now 28, from across the room. He had only seen her at work… modeling lingerie in a Victoria’s Secret catalogue, that is.

“When I was younger, I’d see her in the Victoria’s Secret magazines that my sisters were getting, but it didn’t really come to me [at the party].

When she walked into the room one of my boys was like, ‘You know who that is?’ and I was like ‘No.’” But that didn’t stop him from wanting to get to know her. “[Someone else] wanted to go talk to her, and I was like, ‘No man, let me go talk to her, I’ll pay you, bro; you talk to her friend.’ So I approached her and asked her if she wanted a drink, and we were just talking for the rest of the party, and then we went to some club for the after-party and kept talking. I got her number, and we went our own separate ways, but we stayed in contact. It was kind of crazy. And now that’s my lady!”

Chanel Iman, Sterling Shepard. BFA
Chanel Iman, Sterling Shepard

Photo Credit: BFA

Fourteen months after meeting, the two wed at the Beverly Hills Hotel in Los Angeles in a lavish ceremony attended by A-listers like Chrissy Teigen, Gabrielle Union, Tiffany Haddish, Odell Beckham Jr., Joan Smalls, Jourdan Dunn and Shanina Shaik. Daughter Cali Clay was born five months later. Most pro athletes in their mid-20s would be sowing their wild oats, but not Shepard. He always knew that he wanted a family at a young age. In fact, yes—you know what’s coming—he visualized it! 

“To be honest, it’s something I’ve always envisioned,” he says. “I’ve always been a family type of person. I am very young, but this is just the path that I’ve found my life going on… and it’s something I’ve been looking forward to my whole life.”

Although losing his father at such a young age meant that he didn’t have a strong male role model in his life, he’s up to the challenge of fatherhood. In fact, “I think it’s easy,” he declares. “I’m big on my faith and everything it says in the Bible, like treating people with kindness. I know the way to do it. My family definitely helped me out with that, instilling that into me. I’m looking forward to the journey.”

There’s a long road ahead given that Cali hasn’t yet celebrated her first birthday, but Shepard knows exactly the kind of lessons he plans on teaching her, and the kind of dad he wants to be. “I just want to be her strength, show her the examples that a man should set for her,” he notes. “The respect level for women can be lost, and I want her to know that if a man is not treating you the way that I’m treating you, you’ve got to kick him to the curb. That’s what I’m going to show her by being there for her.”

Though he’s clearly a natural at the parenting game, Shepard will be the first to admit that his life has drastically changed because of it. “When you first enter the NFL, you’re trying to feel your way out and see what the city’s like; it was my first time ever being in New York after I got drafted here. When you get married and have a kid, it definitely slows down your pace a lot. You can’t just get up and go out with your buddies anymore; everything is about the baby,” he says. However, he notes that this has an easy fix: Teammate Saquon Barkley brings his new daughter over for game nights, while fellow Giant Evan Engram stops by for Game of Thrones nights.

Sterling Shepard
Shepard with daughter Cali Clay

Photo Credit: Lev Radin

A more difficult fix is quality time with his leading lady. “You need to find time for your spouse as well,” he admits. “It’s tough trying to find a balance, especially when you have a baby not too far after you’ve gotten married, so you didn’t really get a chance to enjoy the marriage aspect of it. It’s a little difficult at times, but I’m working my way through it.” 

He and Iman have done this by carving out dedicated couple time for one another, which is no easy task with his football schedule and her modeling one, but they make it happen. “We just need one or two days a week where we can just have some alone time; that’s definitely helped us. Date nights are very important,” he laughs, noting that as a couple, they’re pretty low-key, favoring live music, good food and a glass of wine over the crazy club night they might have had even a few years ago.

In fact, they celebrated their first wedding anniversary in much the same way. After a whirlwind trip to Turks & Caicos, on the actual day of their wedding, they rang in the occasion in the best way possible: at home, alone, together. “When we got back from [our vacation], we just chilled,” he recalls. “Sometimes we’ll plan some big stuff and say we’re going to have a get-together or whatever, and then we’ll just sit down and look at each other and say, ‘Let’s go out to eat and come home and watch Netflix.’ So that’s what we did. We came back and chilled.”

“Chill,” according to Shepard, also refers to his style. Which, when you’re married to a supermodel, may not always cut it. “When I first got to New York, I knew it was the fashion capital, but I was big on wearing sweats, being an athlete. That’s all you need,” he says. “When it came to going out with Chanel, I realized, ‘OK, all eyes are on her for sure, but I can’t just be wearing sweats out.’ I upped it a little bit, but not too much. If I’m going out and it’s a flashy place, I wear all black, some Amiri jeans, a Fear of God hoodie. I keep it so simple.”

And while you might expect that a supermodel would be doling out the advice, not receiving it, he says theirs is a partnership and works both ways: “She’ll critique my style if she’s not feeling something I’m putting on; she helps me in that respect. But vice versa—we do that for each other. Although she doesn’t need much help… she can throw on anything and it will look good. She doesn’t need help, but she’ll ask my opinion.”

Sterling Shepard
SWEATSUIT & SNEAKERS: Louis Vuitton WATCH: Zenith

Photo Credit: Scott McDermott

And like the good husband—and the good man—that he is, he’ll give it. Shepard discovered how to treat women in the manner that they deserve from the women in his life: his mother, Cheri, and sisters Shelby and Ashleigh. “It helped me tremendously growing up around women,” he notes. “They showed me the respect you should have for women. My mom is a huge part of that for me: She raised three kids after my father died—by herself, and that’s the definition of strength to me. My respect level for that is through the roof.”

To be fair, most of what he inherently knows about being good, kind, true and fair, he learned from his mother. “[I learned about] working hard and being able to provide for your family, no matter the circumstances,” he maintains.
She also taught him, most importantly, about staying true to himself. No matter how famous he becomes, he’s still a little boy from Oklahoma, hoping for a vanilla football-shaped cake. “[She taught me to] stay grounded and keep being the person that you’ve always been,” he says.

“Never change with the different things that happen in your life, good or bad. That’s what I live by. You might see some people change when they get a contract extension, let’s just say, but I always just live by that rule, and I feel no different.”

When he breaks it down to the nitty-gritty, life is pretty simple for Sterling Shepard. As long as he stays true to himself, focuses on football and loves his family, life can’t get much better. “I have a lot of goals that I want to hit before my career’s over,” he notes. “It’s only for a short time of your life that you can play football, so that’s what a lot of the time that I have is devoted to. I want to be a Hall of Famer, and I have to put in the work to get there, but you have to sneak your family in there, as well. I’m still trying to accomplish different things, and those are being the best dad that I can be every day, the best husband that I can be every day and the best player that I can be, every day.”

Sterling Shepard
SHIRT: Lanvin
PANTS: ALYX SNEAKERS: Veja
WATCH: Zenith

Photo Credit: Scott McDermott

For location purchase, please contact Mae H. Bagai and Ryan Mocan, Sotheby’s International Realty, [email protected][email protected]
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