Steelers GM Omar Khans path to his NFL dream: Monopoly, letters and sleepless nights

Posted by Patria Henriques on Thursday, May 16, 2024

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A young Omar Khan tore open the Monopoly box inside his parents’ home in Metairie, La.

Casting aside the chance cards, the thimble and the top hat, he pulled out the game board … and flipped it over face down. Each year of his childhood, as the NFL Draft approached, Khan collected newspaper clippings from the New Orleans Times-Picayune, Pro Football Weekly and any other publication featuring prospect rankings and profiles. Alongside his father, A.R., Khan carefully pasted the analysis on the back of the game board.

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Then they rummaged through the game closet, doing the same with the boards for checkers, Scrabble, The Game of Life, Candy Land and more.

“By the time draft day came, we had our living room set up,” Khan told The Athletic this week. “We had our own little draft board, and we made our own evaluations.”

On Thursday, Khan will step inside a much more grandiose war room on the second floor of the Steelers’ practice facility. After 20-plus years in the organization, Khan was promoted to general manager in May, succeeding his two-time Super Bowl-winning mentor, Kevin Colbert. This weekend, Khan’s first draft in the driver’s seat could be a memorable one. With three picks inside the top 50 (Nos. 17, 32 and 49), he has an opportunity to put his fingerprints on the franchise.

“It’s a dream come true for me to be in this position,” Khan said during Monday’s pre-draft news conference. “I’ve been dreaming about it for a long time. I feel ready. I wish I was leaving here getting ready to go make our picks.”

GM Omar Khan on the #NFLDraft process: pic.twitter.com/mkl5zNBvyn

— Pittsburgh Steelers (@steelers) April 24, 2023

As Khan counts down the minutes before he’s on the clock, here’s the story of how the proud son of immigrants heeded the lessons of his hard-working parents, persevered and prepared himself for the dream he’s been chasing since childhood.

Before Omar Khan climbed the rungs to reach the top of his chosen profession, his father, A.R., stood atop a ladder with a paintbrush in one hand and one eye on the Super Bowl.

An engineer by trade, A.R. dabbled in real estate with his wife, Carmen. As he fixed up a rental property for the next tenant, A.R. lugged along an old black-and-white TV. He’d watch a play between the San Francisco 49ers and Cincinnati Bengals. Paint a little. Watch a play. Paint some more.

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If A.R. and Carmen were going to make it in America, they knew the importance of keeping their heads down and working, whether it was a Monday, a Wednesday or Super Bowl Sunday.

“To this day, (my parents) are the two hardest-working people,” Omar said. “I mean, they don’t stop. It’s 24/7. They’re in their late 70s now, and they’re still working hard as ever.”

A.R. immigrated from India to earn an engineering degree at Oklahoma University. While chasing his American dream, A.R. simultaneously fell in love with America’s game.

First, he rooted on Barry Switzer’s Sooners alongside his classmates. Later, when A.R. moved to New Orleans, he met Carmen — herself an immigrant from Honduras — and started a family of Saints fans. Soon their house in the New Orleans suburbs was bursting with three kids speaking no less than three languages. There was English, his father’s Indian dialect of Urdu and Spanish from Carmen. Omar still speaks almost exclusively Spanish with his mother, and he remains active in the Latino community in Pittsburgh.

A.R. passed his passion on to the oldest child, Omar. As they bonded over their shared love of the game, Omar became enamored with the hometown team and its tough-nosed linebacking corps of Rickey Jackson, Vaughan Johnson, Sam Mills and Pat Swilling nicknamed the “Dome Patrol.”

By junior high, Omar Khan accepted a tough reality: If he wanted to make a career out of sports, he was never going to be the next great quarterback, like New Orleans fan favorite Archie Manning. But maybe he could be the engineer behind it, like Saints general manager Jim Finks, an inspirational figure who transformed New Orleans from the lovable loser they called the ’Aints into a playoff team.

“I remember my parents asking me, ‘What do you want to do in life?’” Khan said. “From a very young age, they knew exactly what I wanted to do. I wanted to work in football, specifically the NFL. I loved the NFL. I loved the game. It was just a matter of how I was going to get there.”

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Initially, Khan’s parents were just a bit hesitant. They had left their home countries and sacrificed to set their kids up for a better future. They always stressed academics and tried to sway him toward a more stable career path, like being a lawyer or a doctor.

But Khan had his mind made up. He wrote his senior term paper at Archbishop Rummel High School on NFL free agency and enrolled at nearby Tulane University to study sports management.

“They would have loved for me to go to law school and be a lawyer or to get my master’s,” Khan recalled. “It just wasn’t in the cards. There’s always going to be some hesitation when they’re saying, ‘Hey, we’re gonna put all this money and effort into your college education.’ But they were always very supportive.”

Inside Khan’s desk drawer at the Steelers’ South Side facility sits a manila folder overflowing with yellowing letters.

There’s one with the Jaguars’ logo on the envelope. One from the Texans. The Packers. The NFL league office. And so many more.

“Sports management has as much to do with the ability to communicate. Develop your skills in that area because you must deal with many kinds of people,” one reads in former Giants GM George Young’s cursive.

“There are no classes to take to become a general manager in the National Football League. It takes a combination of business education and a full understanding of football, with a little luck,” wrote then-Panthers GM Bill Polian on the team’s official letterhead.

“Do not be discouraged if you are not able to get an internship with your first letter. Don’t give up and keep writing those letters and somewhere down the road you might get a break,” penned Washington GM Charley Casserly.

A letter from then-Packers general manager Ron Wolf. (Mike DeFabo / The Athletic)

While at Tulane in the mid-1990s, Khan began sending hundreds of letters to anyone in the league he could find — general managers, personnel directors, scouts.

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“There was a consistent theme,” he said. “You’ve got to get experience in football. Go volunteer.”

Khan met with then-Tulane and current Dartmouth coach Buddy Teevens. Impressed with his ambition, Teevens offered Khan an opportunity. He started in a copy room working on any task he was assigned.

“I just needed a shot,” Khan said. “I was willing to do anything I could.”

While building his resume, Khan continued to mail letters to NFL teams. He bombarded the hometown Saints, sending them his own analysis of what the team could do to upgrade at various positions.

Meanwhile, unbeknownst to Khan, Teevens had a close personal relationship with Saints GM Bill Kuharich that dated to their days in prep school. Teevens and his wife, Kirsten, are godparents to Kuharich’s third daughter. The Tulane coach put in a good word to help Khan stand out from the numerous other letters Kuharich received each week.

One afternoon, Khan returned home from college to find his answering machine blinking. It was Chet Franklin, the Saints’ assistant general manager and vice president of football operations, asking if Khan might be interested in an internship. Khan grabbed the phone and raced up the stairs.

He still remembers exactly what he wore to his interview: a golf shirt and khaki pants. He still kicks himself for not putting on a suit and tie. As Khan met with Franklin and Kuharich, he saw a hulking figure laboring down the hall. It was Mike Ditka.

“They introduced me to him, and I was like, ‘I can’t believe I just shook my Mike Ditka’s hand,’” Khan said.

Khan also had a hint of luck, as Polian alluded to — or, maybe more accurately, was in the right place at the right time. The new collective bargaining agreement introduced free agency in 1993 and a salary cap in 1994, the same year Khan graduated from high school. Front offices suddenly grew with teams of interns who researched the salary cap and player contracts.

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In 1997, while Khan was still in college, he earned his chance as a player personnel intern and later was promoted to a player personnel assistant.

“The thing that made Omar stand out was, he was willing to do anything,” Kuharich told The Athletic. “There was no job too small. Whether we’re going back five years on contracts by position or projecting salary caps going forward, he was a very valuable asset.”

The Saints deployed Khan as somewhat of an undercover agent when college prospects or free agents visited. Khan, who began with the Saints before he was even legally allowed to enjoy a beverage on Bourbon Street, developed a routine of questions to get players — who were guarded around people of authority — to open up about their visits, contract interest and decision-making process.

He’d tell the Saints which players might be hard to sign and which he thought could fit into their payroll, a skill that’s been helpful in many roles since.

“We put a lot of trust in his recommendations,” Kuharich said. “Even though he was young, he listened. He didn’t try to show everybody he was the smartest person in the room.

“When you asked him questions or asked him his opinions, he wasn’t wishy-washy, which is one thing I really liked,” Kuharich continued. “I was trained by Jim Finks, who said, ‘Don’t be a fence sitter. Stand your ground. You’re not always going to be right in scouting. But have some conviction.’ And Omar certainly was a guy that had conviction.”

Even though Khan was still in college, he earned respect from grizzled football guys twice his age.

“You can put Omar in with owners, you can put Omar in with the commissioner, you can put Omar in with the scouts, you can put Omar in with interns,” Kuharich said. “He fits in perfectly with all those. It’s not too big.

“When Omar spoke, you listened.”

On draft day in Pittsburgh, Khan would settle into a seat in the back of the room alongside legendary scout Bill Nunn, longtime college scouting coordinator Ron Hughes and Steelers icon Joe Greene.

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“He was just like a fly on the wall,” former Steelers coach Bill Cowher said. “Every meeting we’re at, he just sat there and he would listen to what was being done, what was being said. Did he have the experience? Not yet. How do you get the experience? Just sit there and just keep going through it.”

Khan graduated from Tulane in just three and a half years. After four seasons with the Saints, he made the leap to the Steelers at 24 years old. When Kuharich phoned Steelers owner Dan Rooney to put in a good word, he said not to be fooled by Khan’s youth or relative inexperience.

“I was born and raised in New Orleans, and I never thought I’d be leaving New Orleans,” Khan recalled. “Then one day I got a call from the Steelers about a position. The opportunity to work for the Rooneys, I wasn’t going to pass it up.”

The Steelers’ front office was in the midst of a shakeup. Colbert was hired as de facto general manager in 2000 — his official title was director of football operations before he got the GM title in 2010 — bringing expertise in player evaluation from his time in the Lions’ organization. But he needed a salary-cap wizard and negotiator to manage the financial side of the operation. Enter Khan in 2001.

“I think Kevin was so good for Omar, and then in many respects, Omar was really good for Kevin,” Cowher said. “I think it allowed both of them to marry the two things that they did so very well.

“(Omar) had a passion for what he did, and he was intrigued by what he did. … He loved it with a passion, and it became very evident.”

One of Khan’s first negotiations centered on star running back Jerome Bettis. Khan now admits he might have been tougher than necessary. Over time, Khan earned agents’ respect as a stern but fair negotiator who knew the best deals end with all parties being satisfied. Slowly, he evolved the way the Steelers structured contracts, introducing more incentive-laden language, for example. Khan also learned how to manage up, collaborating with hard-nosed coaches and executives.

From left to right, Art Rooney II, Mike Tomlin, Kevin Colbert, Dan Rooney and Omar Khan after the Steelers’ Super Bowl XLIII victory over the Cardinals. (Courtesy of the Steelers)

“Multiple times, I have gone into Omar’s office and shut the door and said, ‘Where are we?! What’s going on here?!’” said Cowher, who has been known to raise his voice now and then. “I think he’s very good with people. He’s a very good listener.”

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Khan did not work extensively in prospect evaluation during the draft. However, he watched quietly as Cowher, Colbert and owner Dan Rooney built a three-pronged consensus — a philosophy that remains intact with Art Rooney II, Mike Tomlin and Khan in his new role.

“There almost has to be a united front. … Two of the three have to agree on something,” Cowher explained. “And the one-third has to understand this is your turn and you have to take a back seat.”

Sitting in the back of the room while scouts read their reports and the three decision-makers mulled their options, Khan added value by researching trade scenarios, an applicable skill as rumors swirl that Pittsburgh might move up in this year’s draft.

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He developed a thick book of previous draft-day trades. That intel proved fruitful, including in 2003 when the Steelers moved up from 27 to 16 to land future Hall of Fame safety Troy Polamalu and later when the Steelers hopped from 31 to 25 to snag future Super Bowl MVP wideout Santonio Holmes.

“As trades are happening during the draft, it would be Omar’s primary responsibility to make that call,” Colbert told The Athletic. “I would say, ‘OK, Omar, get Buffalo on the phone. We want to talk to them about trading up to their pick.’ Then he would keep me advised as to what they were saying.”

Khan took note of everything going on around him, not just the players who were selected but also how decisions were made.

“He was scouting the scouts,” said Doug Whaley, who spent a decade as the Steelers’ pro personnel coordinator and credits Khan for teaching him how to eat shrimp properly at a New Orleans crawfish boil. “He’d know Phil Kreidler likes tough, physical guys. Kelvin Fisher likes athletic guys.

“Those are those little intricate things that they don’t teach you how and you can’t be taught how to do it, except just being around the people.”

Khan couldn’t help himself, as he wrapped owner Art Rooney II in an emotional embrace last May.

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Through 20-plus seasons in Pittsburgh, Khan’s voice and reputation grew within the Steelers’ organization and the broader NFL community. Dating to 2010, he interviewed for several general manager positions, including with the Seahawks, Jets, Dolphins, Texans, Panthers and Bears.

As it turned out, his loyalty to the Steelers and persistence paid off when he climbed the final rung of the ladder with an organization he knows so well. Khan stepped out of Rooney’s office and made his first call to his wife, Kristen. Then, he called his parents.

“My parents have been hearing me talk about this since I was 8 years old,” Khan said. “Just hearing them talk, I think they felt like it wasn’t just me getting the job. It was them also. They had watched me when I was a kid just obsessed with the NFL and football and the way it works. When I called them, I still remember to this day the joy in their voice.”

Omar Khan and Art Rooney II at his introductory news conference. (Gene J. Puskar / Associated Press)

There was also a sense of disbelief. A.R. and Carmen knew almost nothing about football when they set off to make a better future for their family. Now their son had risen the ranks to land one of the 32 most-coveted jobs in his field thanks to the hard-working values they instilled in him.

“I just loved the fact that he’s where he wanted to be from Day 1,” Cowher said. “He chased it. He chased it with vigor.”

In one of his first moves as general manager, Khan enticed Mount Lebanon, Pa., native Andy Weidl to leave his position as Eagles president of player personnel and return to his roots in Pittsburgh as assistant general manager. The two executives forged a relationship that dated to their days together as interns with the Saints.

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Now, just like how the personnel-centric Colbert brought Khan in to balance him out, Khan covered his blind spots by adding the man who set the Eagles’ draft board and expanding the scouting department with other proven talent evaluators. To Cowher, that showed a self-awareness that few possess.

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“He knows his strengths,” Cowher said. “But more importantly, he knows what he’s not as strong in.”

“He’d be the first to tell you that if he got into the position like he did, he was going to need some talented evaluation folks, as well,” Colbert added.

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The move maintains continuity within an organization predicated upon that principle. He knows the Steelers. And the Steelers know him.

But Khan has not been shy about putting his own fingerprints on the franchise. Soon after he was handed the keys, Khan made Minkah Fitzpatrick the highest-paid safety in the league and guaranteed the first two years of the contract. He dealt receiver Chase Claypool to the Bears before the trade deadline in exchange for what became the No. 32 pick, a deal many view as a steal for the Steelers.

“In the past, they would have rode Chase’s contract out, let him move on through free agency and tried to get a compensatory pick,” Whaley said. “The compensatory pick you’re going to get, the highest it’s going to be in the third round. So for him to flip that and get a second-rounder for a guy, he just showed you an evolved way of thinking how you can maximize the system and get a good return on investment.”

More recently, Khan traded almost nothing (swapping seventh-round picks with the Rams) to land veteran receiver Allen Robinson. The Rams are paying about $10 million of Robinson’s guaranteed $15 million for 2023.

“When have you ever heard of a Steeler transaction where someone else is going to pick up salary for a guy?” Whaley said. “Those are the types of things that let you know he’s keeping true to the foundation of what the Steelers are, but evolving your thinking to be able to maximize the different ways you can acquire talent.

“That’s the essence of what I think he’s bringing to the table.”

Mike Tomlin and Omar Khan will work closely with Art Rooney II to make decisions during the draft. (Karl Roser / Pittsburgh Steelers)

While Khan has made it clear he plans to stay true to the Steeler way — “We’re always going to build this through the draft, and I can’t ever forget that, and I won’t,” he said — his free-agency approach also hints changes are coming. While Khan applied what he learned from Colbert and didn’t break the bank, the Steelers have been much more active than typical, adding 10 external free agents.

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“There’s probably a lot of people that can come in here and do it better and do it different,” Colbert said. “And that’s OK. Him staying current with the salary cap and the league happenings, I’m sure he’s going to try to do some things that are more current. And that’s fine. You have to stay with pace.

“But in doing that, and staying current, you also have to understand and realize the foundation of the organization.”

These days, the kid who dreamed about leading a draft now sometimes can’t sleep through the night, as numerous scenarios swirl in his head.

“Andy (Weidl) and I have been laughing at him that he’s been talking extremely fast,” a smiling Tomlin told reporters Monday.

While Khan has his dream job, he maintains the hunger from his college days, when he was beating down doors to get his first step into the league. That’s because, in his own words, Khan hasn’t achieved anything yet.

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“There’s a standard here,” Khan said. “Every day when I walk in this office, I walk by six Super Bowl trophies. I’m motivated to try to get the seventh.

“… And then eighth

“… and then the ninth.

“When I wake up in the middle of the night and I can’t go back to sleep, it’s usually because I’m trying to figure out what can I do today to help make us better to get that next Super Bowl ring.”

(Illustration: Ray Orr / The Athletic. Photo: George Gojkovich / Getty Images)

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