How Scott Boras Became a Baseball Super-Agent

Scott Boras’s emergence as a super-agent over the past 25 years has deeply influenced the course of pro baseball. As an introduction to the man before he became (relatively) famous/infamous, here are excerpts from a couple of long profiles of Boras in the early ’90s. Since the off-season is the time when Boras and his peers are most influential, this is a good time to look at his early career. From the San Diego Union-Tribune of April 1, 1992:

Raised on a dairy farm in Elk Grove, approximately 30 miles from both Sacramento and Stockton, Boras said his dad thought of baseball as a privilege. Only after all the many chores were done was Scott allowed to play or watch a baseball game.

And, although looking more like a stockbroker, Boras still works farmer’s hours. Friends and foes alike say Boras is a tireless workaholic.

“Scott’s a brutal golfer,” said Maddux. “That’s because he works too much, puts in too many hours. We were on the golf course last October and he said, ‘I can’t believe I’ve actually taken two straight days off.’ He sounded guilty about it. I said, ‘C’mon, Scott, relax, willya?’ He couldn’t do it.”

Boras had to burn the candle at both ends at the University of Pacific. Signed by the Cardinals organization, he tried to forge a baseball career while earning a Ph.D. in pharmacology.

“I took my finals at spring training,” said Boras. “I had to have somebody monitor for me. My monitor was my manager, Jack Krol. I’m there taking my finals and he’s right there in the room with me, drinking a six-pack. It was pretty tough to concentrate with him burping.”

Ultimately, finals worked out better than spring training. A promising outfielder until his knees required two surgeries, Boras was moved to the infield, and it was a troublesome transition. He’d pay local coaches to hit him extra ground balls after practice, but in Boras’ case, practice did not make perfect.

“I averaged 32 errors a year,” Boras said. “Fortunately, I always hit .290, so they kept me around.”

For a while anyway. Boras was traded to the Cubs in 1977 and sent back for his fourth and final season in the minors.

“I was the player to be named later for Don Kessinger,” said Boras. “Apparently, the Cubs liked my bat and didn’t value defense.”

A third knee operation made a doctor out of Boras. Out of baseball, he applied his Ph.D. as a research chemist, but that lasted only four months. Ambition took hold again and he decided to seek a law degree.

“Few attorneys have medical degrees, so I thought I could be a successful malpractice attorney,” said Boras. “That, or the president of a drug company.”

Boras became the former, earning his law degree from UOP in 1981 and setting up a practice in Chicago. Two friends and former teammates who’d made the majors, Caudill and infielder Mike Fischlin, drew Boras back toward the game by asking him for legal guidance.

“I really didn’t have an agent I could trust,” said Caudill, a nine-year veteran, now retired and living in Seattle. “My first agent never had time for me, because he was too busy with the veterans. Scott and I had beach bungalows next to each other in St. Petersburg, and I knew even back then that he was honest and fair. There’s just something about him, a truth.”

There’s something about Caudill, too. Trust doesn’t come easy to him. The product of a broken marriage, Caudill said he came home one day and his signing bonus had mysteriously disappeared within his family.

“After that, it became imperative that I be able to trust someone,” Caudill said. “From Day One, I knew I could trust Scott.”

With his life. And with his wife. Caudill said Boras watched over his career, but also his personal life, providing support for Diana Caudill. She said that to this day Boras is probably her best friend.

“I’m not sure Bill and I would still be together if not for Scott,” she said. “When Bill was in baseball, that was his life. There’s not a place for women in this game. We weren’t even allowed to go into the bars the players went to. It was just real frustrating. I had no understanding of it. Scott was always there for me, though, willing to hear my side of it.”

Diana Caudill also recalled how frustrating it was to heed Boras’ advice to remain frugal. You may be making $200,000 a year, Boras told them at the time, but live like you’re only making $35,000.

“He wanted us taken care of,” said Caudill, “not just while I was playing, but for the rest of our lives.”

Now, while most of those who played ball with Caudill have had to find jobs to support their families, the Caudills are living off annuities that will pay off for the next 34 years.

Victory in a tragic Chicago malpractice case made it possible for Boras to become a full-fledged player rep. Representing the parents of a baby who developed cerebral palsy, Boras said he and another attorney proved misuse of medication by a doctor and nurse in the child’s delivery, along with fraudulent record-keeping. Matching the fetal heart rate with the mother’s heart rate and the amount of drugs injected during labor, Boras said, they deduced that the baby was denied sufficient oxygen in birth.

The couple was awarded damages of $3.8 million, one-third of which was split between the two attorneys.

“If I was just interested in money,” said Boras. “I could’ve made more as a malpractice attorney.”

A list of Boras’s clients as of early 1992 included:

Jim Abbott P Angels; Patrick Lennon OF Mariners; Sandy Alomar Jr. C Indians; Mark Lewis SS Indians; Wilson Alvarez P White Sox; Derek Lilliquist P Indians; Jack Armstrong P Indians; Ben McDonald P Orioles; Steve Avery P Braves; Joe Oliver C Reds

Carlos Baerga 2B-3B Indians; Jeff Parrett P Athletics; Tim Belcher P Reds; Bip Roberts OF Reds; Jay Bell SS Pirates; Ivan Rodriguez C Rangers; Andy Benes P Padres; Kenny Rogers P Rangers; Jeff Blauser 2B Braves; Benito Santiago C Padres

Ryan Bowen P Astros; Kurt Stillwell 2B Padres; Kevin Brown P Rangers; Todd Van Poppel P Athletics; Cris Carpenter P Cardinals; Rick Wilkins C Cubs; Alex Fernandez P White Sox; Bernie Williams OF Yankees; Scott Hemond C Athletics

And the Sacramento Bee of April 1, 1993 wrote this about Boras:

It fell to [Donald H.] Wollett, sagely professor at the McGeorge School of Law [at the University of Pacific], to give Boras’ life some definition.

“If you’re a really good lawyer, you’ll know it for one reason,” Wollett told his bright-eyed ex-pupil. “You’ll know it because everyone will dislike you.”

We can only assume, more than 10 years later, that Scott Boras is very, very good.

At age 40, the calculating kid from Elk Grove finds himself as arguably the most powerful agent in baseball. In the 1990s, that makes him an indelible part of the game’s fabric, in the way a coffee stain becomes an indelible part of your favorite shirt or black widows become co-tenants in your dream house.

The game puts up with him because it has to, because Boras simply won’t go away, and because Boras happens to hold the remote that controls everybody from Greg Maddux to Jim Abbott to Sandy Alomar Jr.

But the game doesn’t have to like it. Indeed, if not for the respect and fear they must concede him, baseball’s shakers would surely loathe Boras right off the planet.

“Within baseball circles, I don’t think he’s a guy that anyone wants to find representing their player,” says Chicago Cubs general manager Larry Himes.

“This industry is run by talent,” Boras says. “You know what talent means, and you know that the organizations cannot afford to walk away from talent.

“It has to be exceptional talent. It can’t be just any talent. The key is knowing what is what.”

Boras knows.

He is believed to be the only agent out there with both a minor-league background and a law degree, and the combination has proven electric. Able to scout and identify premiere talent while it’s still green, able to negotiate with a lawyer’s skill on that talent’s behalf, he has hand-picked an all-star roster of clients and showered the group with precedent-setting contracts.

* Andy Benes, baseball’s top draft pick in 1988, a $235,000 signing bonus with San Diego.

* Ben McDonald, a $975,000 package upon his selection by Baltimore in 1989.

* Todd Van Poppel, signed by the A’s out of high school for $1.1 million in 1990.

* Brien Taylor, 18 years old, signed by the New York Yankees out of high school for $1.55 million in 1991.

* Greg Maddux, jumping from the Cubs to the Atlanta Braves this season for $28 million over five years – and spurning a $35 million, five-year offer from the Yankees to do it.

The owners warned him to stay away from their high amateur draft picks; he ignored them. They tried to restructure the amateur draft to undermine him last year; he fought it, and won.

More than once they’ve threatened to freeze him out, influence all players of any value to avoid him. Former Seattle Mariners owner George Argyros once looked him in the eye across a bargaining table and called him a “young punk.”

Boras just kept talking.

“Owners control their own destiny,” Boras says. “I have no control over it. My only function in this system is market definition. And the owners have exclusive control as to accepting that definition.”

Leverage is leverage, and from the start Boras always had an amazing aptitude for building kingdoms atop the tiniest toeholds. Even before he studied law, he shrewdly negotiated his own minor-league contracts after being drafted by the St. Louis Cardinals out of the University of the Pacific.

“The way I negotiated my contract had nothing to do with what I had to offer them,” Boras says. “I negotiated it on the basis of what I was not earning practicing with my pharmacy degree. I said, “Hey, I’m giving up a lot of money to play professional baseball,’ which I was.

“So consequently they paid me very, very well, by (minor-league) standards. I mean, one year I made like $19,000.”

His real antagonism toward the game didn’t begin until 1983. By then he’d long since terminated his five-year stint in the minors, made a stop at McGeorge, and gone to work using his law and pharmacy degrees as a malpractice lawyer in Chicago.

Fischlin and Cubs pitcher Bill Caudill were his only baseball clients, mostly because both were former teammates – Fischlin at Elk Grove High School, Caudill in the Cubs’ farm system.

Then one day Boras approached Tim Belcher, the first-round draft pick of the Minnesota Twins, and Kurt Stillwell, the first-round pick of the Cincinnati Reds. He sold himself as the only lawyer/ex-player they would ever find in the agent business.

Both players bit and a war was born.

“The Twins called and said, “You don’t come in and represent drafted players. If you’re any kind of a real agent, you’ll represent players who are already in the big leagues,’ ” Boras says.

“And I just kind of went, “Oh, yeah?’ ”

Boras advised Belcher to turn down the Twins’ offer of a $110,000 signing bonus, and wait for them to sweeten the pot. The Twins were flabbergasted, and indignantly suggested to Belcher that Boras was giving him self-destructive career advice.

Belcher was coming off his junior season at tiny Mount Vernon Nazarene College in Sparta, Ohio. The Twins maintained that if he spurned their offer and re-entered the June draft after his senior season, clubs would pay him far less because his college eligibility would be up and he’d have no other options.

Boras knew better.

Since Mount Vernon was an NAIA school, it was not subject to the NCAA rule that disallowed players from re-entering the draft until they’d used up their college eligibility. Belcher wouldn’t have to wait until the following June; he could turn down the Twins and still be eligible for the winter draft, where the deep-pocket New York Yankees were waiting with the No. 1 pick.

The Yankees came through with a contract some $50,000 richer than what Minnesota offered. The Twins were left with a premiere no-show and, before long, vacancies in their scouting department.

The underlying market was suddenly exposed in all its fertility, and it was Boras who had the tools to harvest it. After getting Caudill a landmark contract with the Toronton Blue Jays in 1985, he quit malpractice law and began logging thousands of air miles on scouting expeditions, all in an effort to tap the can’t-miss draftees before they were drafted.

“I had general managers telling me, “Hey, work with us. Don’t represent these drafted kids. We’ll let you know who our prospects are in the minor leagues,’ ” Boras says.

“Well, I don’t need you to let me know who the prospects are. I can go out and watch them for myself.”

Two years ago, the Cubs liked what they saw from Maddux and offered him a four-year contract worth $7 million. Boras spent three days in a hotel room with Maddux, persuading him not to lock into a long-term deal because his marketability hadn’t peaked.

“It takes a great amount of guts on the part of the player to do that,” Boras says. “But that’s the magnitude of the decisions in our business. If Greg had signed that contract, he’d be guaranteed $7 million over four years. Right now he’s got one for $28 million. So that’s a $21 million decision.”

Finally, as a long epilogue to this story, here’s the Sacramento Bee of Sunday, February 24, 1985, describing how Boras had just gotten his breakthrough deal for Bill Caudill: a five-year, $8.2-million contract. It’s very detailed, but should interest you if you want to learn more about how and why major league salaries began really shooting upward in the later ‘80s:

Boras is different. Caudill sensed this when they played together a decade ago in the rookie league at St. Petersburg, before a knee and good sense diverted Boras to the practice of law.

Caudill became convinced when Boras just showed up one day in Chicago, unsolicited, a guy he hadn’t seen for years, and said he thought he could help.

Caudill needed the Lone Ranger’s sort of help, not merely an agent’s.

He was in his third year with the Cubs that summer of ’81 and had fallen apart. His earned-run average was around half a dozen. He seemed beyond the help of all the king’s horses and all the king’s men.

I’m going to make you famous, Caudill remembers telling him. Caudill is like that.

Said Boras, who isn’t, normally, I’m gonna make you a million.

He got it and then some.

HE GOT CAUDILL a contract last week that will bring him approximately $8.2 million over five years, $1.64 million a year, sixth or seventh best in all baseball behind George Foster ($2.04 million), Dave Winfield ($2.02), Mike Schmidt ($1.91), Gary Carter ($1.87), Rickey Henderson ($1.7) and possibly Bruce Sutter ($1.6).

With the money funneled by Boras into annuities and such, Caudill will realize, in the course of three decades, around $35 million.

Too much, concedes Caudill, for one man to spend.

Boras got the contract on the 25th floor of a Chicago hotel, eight minutes before an arbitration hearing that would have committed Caudill to a one-year agreement.

He got it going up against older men, powerful, intimidating men. He got it, being careful to give the appearance, he would say later, that I was willing to take them to the wall.

He got it, though he didn’t sleep the night before worrying about it, and his shirt was wet underneath his jacket as he bargained it out. He later admitted he was more than just nervous.

He said he was scared.

The biggest day of my life, Boras called it as he posed with his client for Sports Illustrated’s photographer.

This is how it came down

NO REPRESENTATIVE so young had ever won a contract so large. Certainly not Scott Boras , who represents Caudill and the Indians’ Mike Fischlin and nobody else you ever heard of – yet.

The best he’d ever done across a bargaining table was the $690,000 he had gotten for Caudill last year in Oakland. It was the third successive one-year contract he’d bargained for his client.

The Blue Jays weren’t particularly interested in a one-year contract, Boras sensed. They had given up a starting shortstop in Alfredo Griffin, a starting left fielder in Dave Collins, and $320,000 in cash to pry Caudill loose from the A’s.

The two salaries plus the cash added up to $1.54 million, and you do not give up $1.54 million of your property to secure a relief pitcher for only one season.

But the initial overtures of Jays’ vice president Pat Gillick were restrained, and so Boras persuaded Caudill to seek arbitration.

He’s always been true to me, and fair, and honest, and straight to the point, Caudill said the other night. I’ve always followed his advice.

Judge him by his brains, not his hands. That’s why he can’t play. That’s why he’s a lawyer.

ASSUMING THE JAYS wanted a long-term agreement with the 28-year-old pitcher, Boras reasoned the threat of arbitration would lend urgency to the talks. Arbitrators award one-year contracts. The player can file for free agency when the contract expires.

The Jays filed an offer of $850,000 with the arbitrator. Boras settled on $1.3 million because Goose Gossage was getting $1.27 million from the Padres, and Boras contended his relief pitcher – who had a 9-7 record, a 2.71 ERA and 36 saves for an Oakland club that was perfectly dreadful, last in the league in pitching, last in defense, 10th in offense – was better than Gossage.

To win in arbitration, he would have to prove it.

Even the Players Association warned he wouldn’t win last Wednesday’s arbitration hearing.

The same arbitrator was to hear Leon Durham’s case that very same morning. Durham hit .279, belted 23 homers and drove in 96 runs for the Cubs, and the association’s attorneys figured he was a lock to win a record $1.1 million award.

No way, they reasoned, would the same arbitrator make two consecutive record awards.

But Boras persisted.

Toronto lost to Detroit by 15 games [in 1984], he reasoned. Toronto lost 18 games where they had the lead entering the eighth inning. Take Bill’s save-versus-opportun ratio, 36 of 43, which is 85.4 percent, and multiply that times 18. That comes down to 15.1 games – the difference between Toronto and the divisional crown.

Boras had done his homework.

Homework tends to impress arbitrators.

Boras, who moved his law practice into a Chicago high-rise a couple of years ago, has a $100,000 overhead there. Part of that goes to rent space on the computer at the University of Chicago. There, he keypunched in every imagineable statistic for the past 10 baseball seasons, just to help with his homework. This is how things are done in the bigs by bright, ambitious 31-year-old 99 guys.

There was one conversation between Gillick and Boras about baseball statistics. We went at it an hour, Boras reflected. He saw that I knew my stuff.

Presently, the Jays firmed up their offer, just like he figured.

They offered $6.25 million over five years.

Boras rejected it.

TUESDAY, THE NIGHT before the arbitration hearing at Chicago’s Hyatt Regency Hotel, the Jays phoned to present one last offer.

They insisted on presenting it to Boras and Caudill together in the Jays’ suite at the Hyatt.

Said Caudill, I figured it was a ploy to get Scott and myself at each other’s throat.

I don’t want you to even look at the paper, Boras told him. I want you to just take it, fold it, put it in your pocket and walk out.

Caudill did, remembering to say thank you and shake hands. Gillick was ashen-faced.

Come to find out, said Boras, they thought we weren’t even going to look at their offer, just go to arbitration, and Bill was going to become a free agent. They thought Bill didn’t want to play in Toronto.

If Bill walks, the Toronto papers were saying, so would Gillick, though less willingly.

Back at Boras’ apartment, Caudill, Boras and Don Wollett, Boras’ professor at McGeorge, studied the document. Wollett arbitrated the Pedro Guerrero case a year ago. He knows the business. Boras had thought his council would be handy, and flew him in for the purpose.

The Jays had come up substantially this time, they noticed.

Still, nobody slept very well.

WHAT’S THE WORST thing that can happen? Boras asked Caudill as they drove to the Hyatt Regency the next morning. We lose the arbitration. You get $850,000. Maybe you get hurt, and we collect the $3 million on our Lloyd’s of London policy. Or next year, maybe we even do better than what we’re asking for now.

It was time for brave dialogue.

I knew the case, Boras later conceded. The only question was, could I talk?

Shortly before 9 a.m., as prearranged, Boras, Caudill and Wollett walked into the Blue Jays’ suite on the 25th floor. The arbitration hearing downstairs was set for 9:30. Across from them sat Gillick and Paul Beeston, another vice president, each doing his best to seem wise and intimidating.

Will you entertain a counter-proposal? asked Boras. There is no such thing, he suggests, as a final offer.

No, said Gillick.

See you at the meeting.

Boras turned to leave.

No, wait, said Gillick.

Everyone sat down again.

At 9:10, the contract was a firm $7 million over five years, structured precisely as Boras had wanted. Gillick and Beeston left the room. Boras turned to Caudill.

Do you want to spend five years in Toronto?

Yeah, I do, said Caudill.

He was ready to sign.

Boras wasn’t.

OK, HE SAID, BUT I want incentives in the contract, to allow you to become the highest-paid relief pitcher if you perform really well.

I don’t think they’ll give ’em, said Caudill, uncertain about pressing it.

I think they’ll give ’em, said Boras. He looked at Wollett, who nodded a nod that said they would give ’em. It was 9:18 by Boras’ watch.

God, I never thought I’d get this kind of money, said Caudill to no one in particular.

Gillick and Beeston came into the room.

Boras said he wanted this, that and the other, listing incentives that would lift the value of the contract to $8.2 million, probably, or even $10 million if Caudill strikes out every batter he faces the next five years.

As he spoke, Boras worried way in the back of his brain that the next demand might be the one that screws everything up.

I could tell he was nervous, said Caudill. And I’m sure he could tell I was, too. Who wouldn’t be, if they were in their right minds and had any sense, talking about that kind of money?

But there was something in Gillick’s eyes, a desperate eagerness, that encouraged Boras to press.

He pressed, and Gillick said yes, yes, yes, and finally Gillick extended his hand and said, We have a deal, then?

Boras nodded.

Gillick produced a bottle of champagne and a handful of long-stemmed glasses, and it was done.

It was 9:22.

Afterward, Caudill said: “It (the negotiations) might have taken a couple of years out of my life but I’ll survive.

“I think we’ve both come out winners. Toronto’s got me for what I consider will be the prime of my career and I’m just on top of the world right now.”

“I’m glad it’s over and there’s a great deal of satisfaction knowing that I’m secure for the next five years and I have nothing to worry about except baseball.”

Years later, long after Caudill left major league baseball, he looked back: ‘”There were things about Scott that I always respected. I knew he was honest, and I could always trust him. When I got to the big leagues, I got a call from Boras and, when he told me he was interested in getting started (as an agent), I hired him on the spot.”

Published in: on December 4, 2010 at 10:33 pm  Comments (1)  
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One CommentLeave a comment

  1. Great read, and at least there’s a potential path of how to become an agent, I don’t know if it applies in 2012, but I’m working at it 🙂

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