The Almost (but Not Quite) “Client”

James L. Robertson

Article by James L. Robertson Featured Author


If you open the front cover of John Grisham’s novel, The Client, you’ll see the usual stuff. Title page. Copyright 1993. Stop at that one. No one begrudges John’s claiming copyrights in the book, and the tale so well told. But not the title. That word, “client,” is still out there to be used by lawyers and others as appropriate. Besides, John would be the last to take offense at a Mississippi lawyer bragging about having Gladys Montgomery as a “client,” formally or otherwise. Provided that client-lawyer relationship was practiced — and cherished — in the proper professional loyal and caring way.

What follows is a story of race relations, Mississippi variety. And building upon a particular instance of such relations, the story of a “client” like the fabulous fish, nibbling, oh so close but never reeled in, then for years so admired from afar. Only in Mississippi?

Gladys Delores Montgomery was born on October 31, 1934. I was not born until July 30, 1940. By then, Gladys was three months short of becoming a six year old herself. In time, all would come together in L. D. and Susie Lawton Robertson’s modest residence at 818 Cedar Street in Greenville, Washington County, Mississippi.

I was a teenager during the years when Gladys was a housekeeper in the Robertson home. More accurately, I was a particularly self-centered teenager during those years, no doubt in substantial part because my mother made me feel as though I was the very important center of the Universe. My younger brother and two younger sisters completed the household.

I was just finishing up my tenure as an 8 th grader on May 17, 1954, when the U. S. Supreme Court decided Brown v. Board of Education. I more or less understood what the Court had said. My primary concern was that interracial sandlot baseball that I had enjoyed for any number of summers was suddenly off limits. None of the white guys who were my friends were allowed to come to Sportsman’s Park — a hop, skip and a jump from Coleman High for the black kids — and play ball.

Over the years I have often reflected on the summer of 1954. In candor, I’ve never been quite sure to what extent reduced sandlot baseball was a function of the fact that girls were becoming much more interesting than I had theretofore thought.

When Gladys Was Our Housekeeper

It was during my high school years — early post Brown years — that Gladys was “the help” in the Robertson home on Cedar Street in Greenville. The homes of most of my friends had not dissimilar housekeepers. I remember Gladys from those days. She was a big woman. Not fat. Just, as the saying went, a big boned woman. And, of course, her skin was black.

I have no memory of any awareness that, while she was housekeeping in the Robertson home, Gladys had given birth to three sons, the last of whom was born on July 1, 1956. Of course, I had no idea that in time Gladys’ no. 3 son, Cleotha Montgomery, would be wearing a Super Bowl XVIII (18) championship ring for his play with the NFL champion Los Angeles Raiders. The only reason that Cleotha’s more prolific, almost two years older big brother didn’t have a ring from the next year’s Super Bowl was that no. 2 son Wilbert’s defensive teammates on the Philadelphia Eagles could not stop the Raiders’ offense. 1

Nor did I foresee that I might one day become a lawyer, much less that as a lawyer I might begin some connivance as to just how I might gain Gladys’ confidence as a de facto client, as soon as the sons of Gladys might become hot items for drafting, recruitment and contracting by National Football League teams.

When My Connivance Began

By 1965, nonetheless, I had become a lawyer. “Admitted to the bar,” as the saying goes. I was one of five with a downtown Greenville firm led by soon-to-be-U.S. District Judge William C. Keady and Greenville School District President Roy D. Campbell, Jr. 2 Fred DeLong, down from Tutwiler and as crafty in the courtroom as any I’ve known, and Billy Keady, Jr., more my age, rounded out the five.

Fast forward to the Fall of 1971. Along with so many other Greenville High School Hornets football fans, I was often in speechless awe at the gridiron skills and achievements of Gladys’ second and third sons. Several other young lawyer contemporaries and I began to twit each other about who could negotiate the best pro football contract for the Montgomery boys. Wilbert was the best high school running back any of us — or likely anyone else anywhere else, for that matter — had ever seen. Cleotha, a grade — or was it two — behind his brother, was a wide receiver and punt return specialist. At least, at the time that’s how he was slotted. The Hornets were state champions that year, and then co-champs in 1972.

I kept my mouth shut about my ace in the hole. More of a touch of anxiety how Gladys might recall what, as far as I knew, had been her first job. Did Gladys remember me? What were her thoughts? I had no doubt at all about the closeness and other nuances of mother-son relationships in that community.

But college was first. For Wilbert’s senior year at Greenville High, the college scouts and less formal representatives were swarming. Ole Miss folk were in touch with me and several others. Everyone was looking for an angle. I saw Wilbert’s high school record. I can’t recall exactly how it happened, but I came to understand just who Wilbert was.

Or, rather, to confirm who Wilbert’s mother was; herein of “the client.” And all of the above had led to confirming what a powerful influence Gladys was on the lives and futures of her sons. I was not the only young lawyer in Greenville well aware that Wilbert was a definite NFL prospect, and that in time he was going to need a lawyer. And suspecting that Gladys was going to have quite a “say so” in all aspects of Wilbert’s future. For all practical purposes, Gladys was going to be “the client,” and we all knew it.

A Mother’s Fear of Football Injuries

Many a mom worries about her son playing football and getting hurt. No racial divide on that one. This fear quickly became a reality for Gladys Montgomery. The 1967 season for powerhouse Coleman High, in at-that-time — Brown notwithstanding — still segregated Mississippi high school football, had not begun when Gladys’ oldest son was suffering injuries. Born in May of 1949, Alfred “Bimbo” Montgomery was looking forward to his senior year, 1967. After all, he had been switched from guard to running back. But it never happened. As a journalist put it later, “Wilbert’s older brother[] back in Greenville was injured playing football years ago. Gladys Montgomery outlawed football for the rest of the family.” 3

The matter quickly became more complicated. The year before, little Daren Dewayne Montgomery had been born. In October of 1971, the then five year old child “died at his home after a lengthy illness. He had been an invalid since birth.” 4

Bimbo and Wilbert

But the story of Gladys’ first son is foundational. Many have long argued, and remain of the view, that Bimbo Montgomery was the best of all of the great football players who came out of the Montgomery family in Greenville. The Los Angeles Times once reported that Bimbo “is considered by the family as the most talented athlete, but his career was shortened because of injuries.” 5 Not too many years later, Wilbert overheard his mother comment on a football radio announcer’s mention of his name. “She thought it must have been another Wilbert Montgomery, because her son didn’t play football.” 6

As fate would have it, no Southeastern Conference school could successfully recruit Wilbert. After flirting with Jackson State College, Wilbert wound up at Abilene Christian University in west Texas, where he broke every record anyone ever heard of. The rest, as they say, is history.

Mama’s concerns notwithstanding, Wilbert had the most productive pro-football career of all of the Montgomery boys. The one-liner that says all is “The Eagles’ Wilbert Montgomery has a history of injuries — but more often than not it’s Philadelphia opponents who get hurt by him.” 7

Cleotha Montgomery

On July 1, 1956, some 22½ months after Wilbert’s birth, Gladys gave birth to Cleotha, still in Greenville. Housekeeping for the Robertsons was long past. During Wilbert’s eye popping senior season with the Greenville High School Hornets, Cleotha was his big brother’s perfect complement. In addition to catching passes as a wingback, after quarterback Bill Hammett had faked a handoff to Wilbert, Cleotha was also a defensive back who got more than his share of interceptions. He also returned punts for touchdowns. After a senior year on his own, Cleotha followed his brother to Abilene Christian.

Cleotha’s college career on the same team with big brother Wilbert should have been illegal. 8 It certainly wasn’t fair to the opposition.

Cleotha spent four years (1981–1985) with the NFL’s Los Angeles Raiders, primarily returning kickoffs and punts. And he had that Super Bowl ring. Two more years with other NFL teams followed.

Willie Earl Montgomery

Willie Earl Montgomery was the next oldest boy in the family. He was a running back, who followed Wilbert and Cleotha to Abilene Christian, where he suffered a knee injury which ended his football career. 9

By this point it was crystal clear that there was a plentiful supply of Montgomery football players in Greenville, such that would be contract counsel should not give up. One could bet the farm that Gladys had only been reinforced in her fear of injuries to her boys. Equally clear, however, the world open to the Montgomery boys was now so much bigger than mere Mississippi.

Jerry Montgomery

Jerry Montgomery was a wide receiver who played college football at Cal State Long Beach. Jerry came back much closer to home for pro ball, as a wide receiver with the New Orleans Breakers of the now-defunct United States Football League [USFL]. 10

Leonard Montgomery

Leonard Montgomery was a running back who attended Cal State Long Beach. In his senior year, Lenny rushed for more than 1,000 yards and caught 50 passes, before suffering a career ending knee injury. 11

Fred Montgomery

Then there was Fred Montgomery, a wide receiver with the Philadelphia Eagles, who had established school punt return records at New Mexico State University, 12

Tyrone Montgomery — Runt of the Litter

Tyrone was the youngest Montgomery, courtesy of Gladys and Greenville. He was the first to stay in Mississippi for any part of his college experience. After two years of junior college play at Tyler Junior College in Texas. Tyrone spent his last two years at Ole Miss as a wide receiver. Lamentably, albeit confirming Gladys’ perennial fears, Tyrone suffered football injuries both of his seasons in Oxford.

Tyrone arrived in Los Angeles in time for the 1993 NFL season. Los Angeles Times sports reporter and staff writer Lonnie White soon pieced together the Montgomery family story, which he summarized and published as “Into the Breach: Raiders’ [Tyrone] Montgomery Has Family Tradition on His Side as the New Third-Down Back.” 13 In addition to his time with the L. A. Raiders, Tyrone also played for the St. Louis Rams.

Fifteen years later, Gladys’ youngest was found visiting the High Desert Premier Academy in Apple Valley, California. Tyrone told middle school and high school students of the trials and hardships he had faced growing up without a father, and that “he and his 11 siblings were the first in their family to graduate high school.” 14 He credited a “father figure” — no doubt Wilbert — who challenged him and his siblings. Then Tyrone added

“No matter what vicious cycle you guys are going through at this point in your lives, you can break through and you can turn the dynamics around in your family so that those who are coming up behind you don’t have to suffer and go through what you are going through… This is your moment.” 15

The Montgomery Family — Full Circle

In the interest of journalistic completeness, it need be added that Roosevelt Montgomery, the boys’ “dad was a brick layer.” 16 Wilbert was once asked about his dad years earlier, and the Clarion Ledger had reported, viz., otherwise tabbed a bridge-welder, Gladys’ significant other left home when Wilbert was in junior high. “Ten kids is too much for anybody,” Wilbert said philosophically. 17

The boys also had two sisters, in time Marsha Linn Montgomery Pruitt and Rosalyn Montgomery Williams. I’ve been unable to find much about younger brothers John and Anthony.

Gladys’ boys tied the Browner brothers from Warren, Ohio — Ross, Jim, Joey and Keith — for the most brothers to play in the NFL since World War II. Tyrone argued that all nine Montgomery boys “really could have played in the NFL. Whatever the NFL record is, we could have broken it.” 18

At the end of the day, Gladys Montgomery — once the housekeeper at 818 Cedar Street in Greenville, MS — had raised ten boys who went to college on football scholarships. Eight earned college degrees. Five played football professionally, four in the NFL. Two wear Super Bowl championship rings. And Gladys — in whatever iteration she may be enjoying — proud though she no doubt is, can rest easier that her boys won’t get hurt playing football anymore.

But what about those grandsons?!?

“the Client” That Exceeded All Expectations

Oh, yes. “The client” never materialized, formally, that is, for yours truly or any of the other Greenville area lawyers. No SEC school had dared touch Wilbert, who’d had a disastrous high school academic record. I have long thought this was in large part because of administrative snafus in the reorganization of the high school component of the Greenville public school district. Alexander v. Holmes County Board of Education had been decided in late 1969. Wilbert’s 10 th grade year was the year of the big transition and, by all accounts, a disaster for many, not just the innocent ones, the students.

Why Wilbert left Mississippi for Texas doesn’t much matter now. Yet, “going to Abilene showed a lot of Mississippians they can go outside the state and get a better education,” he once said. “My idea of going to Abilene was about the education, because pro football was not in my mindset.” 19 Two of my sons and a number of Greenville ex-pats were in Jackson on that evening in the Summer of 2018 when Wilbert was enshrined in the Mississippi Sports Hall of Fame. Wilbert had brought his son from Maryland down to Jackson for the occasion.

No one at the Greenville table doubted that Gladys was there in spirit.

Wilbert Montgomery was humble and appreciative of this recognition accorded by his home state. “It’s an honor and blessing,” he said. “Not only for family and friends, but for people who I’ve come in contact with along the way.” 20 Yet, truth be known, of the six athletes enshrined that evening, only one other had athletic credentials remotely approaching Wilbert’s. 21 And it was absurd that Wilbert, who had been honored so often and for so long in NFL circles across the country, had to wait twenty plus years for his home state to accord recognition. I rather suspect most any good lawyer could establish the proposition that Wilbert’s race had had more than a bit to do with his being so belatedly honored.

Nonetheless, the Wilbert we honored that evening was still ever so much the son Gladys had birthed and raised so many years ago. All things considered, Wilbert, Cleotha and their brothers have done rather well without the assistance of Mississippi lawyers. Yet it’s sad that all left Greenville and their home state, never to return except for visits.

No doubt, Wilbert could have invited his family to Jackson for the events that first week in August of 2018. No doubt the special circumstances of the family that Gladys Montgomery reared could have justified an extra effort on the part of Mississippi Sports Hall of Fame. For the moment it may be enough (1) that Wilbert accepted his enshrinement with such humility and class, (2) that MSHOF has a number of additional opportunities ahead, and (3) that maybe it’s better that some would-be “clients,” like some beautiful bass or trout, slip off the hook or avoid it altogether.

But Gladys’ painfully shy mama’s-boy contributed in another way. He allowed author Edward J. Robinson to use his class countenance as the vehicle for telling the story of young black men trying to make it in the American world of sports. 22 And of how men like Gladys’ son, Wilbert, did so much to blur the racial divides that are a lot less with us than before.


Anyone want to wager, or just guess, what John Grisham could do with Gladys’ story? And what he would name that book, “The Client” having been used up, and maybe wouldn’t be such a good fit anyway.

And what such an effort by John, that born and bred Mississippi lawyer, my former student from teaching days at the U of M Law School, could do to advance the ball further towards the eradication of racism in our state.

  1. Wilbert Montgomery had a substantial and impressive coaching career in the NFL, once his playing days were over. As running-backs coach for the Baltimore Ravens, Wilbert earned his ring in Super Bowl XLVII (47), when the Ravens defeated the San Francisco 49ers.
  2. Roy was the father of Roy D. Campbell, III, former president of the Mississippi State Bar and for a number of years now, practicing law in Jackson with the Bradley firm.
  3. Clarion Ledger Jackson, Mississippi, Sat. Jan. 24, 1981, page 20.
  4. Daren Montgomery, The Delta Democrat-Times. Page 23 (Sun. Oct. 17, 1971)
  5. Lonnie White, “Into the Breach: Raiders’ Montgomery Has Family Tradition on His Side as New Third-Down Back,” Los Angeles Times (Aug. 17, 1993);
  6. Clarion Ledger Jackson, Mississippi, Sat. Jan. 24, 1981, page 20. As fate would have it, Bimbo died on August 1, 2010, at age 61. Gladys died two days later. She was 75 years old.
  7. Rick Ostrow, Eagles Running Back Wilbert Montgomery is a Gamebreaker, Playing with Pain, Pro Football Hall of Fame Official Site;; Wilbert Montgomery’s complete record for his nine year career (1977-1985) with the Eagles is found at Wilbert Montgomery Stats;;
  8. See Greg Jaklewicz’ article, “Wilbert and Cle – oh brother, they were special,”
  9. Lonnie White, “Into the Breach: Raiders’ Montgomery Has Family Tradition on His Side as New Third-Down Back,” Los Angeles Times (Aug. 17, 1993);
  10. Id.
  11. Id.
  12. Id.
  13. Id.
  14. “Tyrone Montgomery inspires students at High Desert Premier Academy,” Apple Valley Unified School District News, April 10, 2019;
  15. Id.
  16. Ron Higgins, “Wilbert Montgomery’s path to Mississippi Sports Hall of Fame has surprises,” Mississippi Clarion Ledger (Oct. 24, 2018).
  17. Clarion-Ledger (Jackson, Mississippi), Sat. Jan. 24, 1981, page 20; Newspapers by Ancestry,
  18. Lonnie White, “Into the Breach: Raiders’ Montgomery Has Family Tradition on His Side as New Third-Down Back,” Los Angeles Times (Aug. 17, 1993);
  19. Ron Higgins, “Wilbert Montgomery’s path to Mississippi Sports Hall of Fame has surprises,” Mississippi Clarion Ledger (Oct. 24, 2018).
  20. Id.
  21. Ron Oswalt, pitcher, a graduate of Weir High School and Holmes Junior College, then foremost starter with the Houston Astros, who concluded his career with strong showings with the Philadelphia Phillies, and two others. The four other inductees were also white. See Inductees, Mississippi Sports Hall of Fame (2019),
  22. Edward J. Robinson, Wil the Thrill: The Untold Story of Wilbert Montgomery (Sport in the American West), published October 15, 2013.