The All Scott Boras Contract Team

Alex Rodriguez has been Scott Boras’ most lucrative player to date. (via Keith Allison)

The year was 1997, and Greg Maddux was finishing one of the best pitching runs baseball had ever seen. He won four consecutive Cy Young awards from 1992-95, a World Series title in 1995, and a National League pennant in 1996. The National League had not known another Gold Glove winner at his position since 1989 (and wouldn’t know another until 2003). Additionally, 1997 was his fifth consecutive season of 7.0 WAR or higher, his seventh consecutive season with 5.0 WAR or higher.

He was wrapping up his age-31 season, but there was little concern about his possible decline, or the 2,598.1 major league innings he had already amassed. Nonetheless, super-agent and metaphor extraordinaire Scott Boras made Maddux baseball’s first $50 million man when he and the Atlanta Braves agreed to a record-breaking five-year, $57.5 million extension.

But Maddux wouldn’t hold the record long. Boras would break the nine-figure barrier just a year later, when the Dodgers signed an older, less accomplished Kevin Brown for seven years and $105 million. This time though, Brown was a free agent. He was the original boat dock in the free agent America’s Cup. We just didn’t know it yet.

Both pitchers rewarded their respective clubs with high levels of performance. Maddux went on another run that was almost as good as the one before it, and Brown, while a lesser success, still gave the Dodgers three elite years before getting traded to the Yankees after the 2003 season, five years into the deal. Because Brown battled injuries at times and failed to lead the Dodgers to the postseason even once, pundits considered it a bust. When he was on the bump, though, he was still as good a pitcher as any, even from ages 34-38.

Since Brown’s contract, struck an even 20 years ago, Boras has negotiated nine-figure deals at eight of the nine positions on the diamond. Most recently, he was the man behind Bryce Harper’s 13-year, $330 million mega deal — the latest of Boras’ record breaking variety. Baseball is a much different game now than it was in the late ’90s, and while the Braves benefited from signing Maddux and the Dodgers Brown, other teams (see Barry Zito, San Francisco Giants and Chris Davis, Baltimore Orioles), haven’t had quite the same results.

This offseason has given us four record-breaking contracts. First, Manny Machado (represented by agent Dan Lozano) became baseball’s first $300 million free agent after signing a 10-year deal with the Padres. Shortly afterward, the Colorado Rockies made one of their own, Nolan Arenado (of Wasserman, and formerly of Boras), the highest paid position player in terms of average annual value, agreeing to a seven-year, $234 million extension. Boras, not to be outdone, helped Harper ink a 13-year, $330 million deal with the Philadelphia Phillies, the largest total contract in major league history to that date.

Then, just when we all thought we would have to wait two whole years to see what Mike Trout would get on the open market, he, along with agent Craig Landis, shattered all three of those deals (as well as distract us from getting any work done), signing the largest contract in the history of American sports earlier this week.

As a baseball fan, there are two things that are unavoidable for me every offseason. First, there is my seasonal sadness that baseball is over. And second, there is the reliable injection of Scott Boras into my daily baseball news consumption. While other high profile agents may not be household names, Boras is just as much a public figure as many of his clients are. For many players, he represents a one way ticket to “Playoff-Ville.” This year, the destination was Philadelphia and Bryce Harper was the one on board.

So in the wake of these record breaking deals, I got to thinking about the other deals he’s had his hand in. If a lineup of his highest paid clients took the field, what would it look like? Would they, too, help their teams buy a house in Playoff-Ville? Or would they financially strap their teams, forcing them to rent an apartment on the outskirts of Tank-City?

I wanted to do this not just to provide historical context, but also to provide insight as to what the future might hold. While Boras is no longer the only one orchestrating record-breaking deals, it is impossible to ignore the impact he has had, and will continue to have, on the game of baseball. Further, it’s hard to imagine where the state of free agent contracts would be if it weren’t for him. With that said, what follows is a list of the highest Scott Boras contract by position. This is, for better or worse, the All-Scott Boras Contract team.

Catcher: Ivan Rodriguez– Detroit Tigers

Four years, $40 million
Best season: 2003- 137 wRC+, 4.7 WAR
Total WAR: 11.3

Pudge was the total package during his time as a Texas Ranger. From 1997-2002, only 12 position players were more valuable, and only Mike Piazza paced him as a catcher. In 1999, he won the American League MVP, producing a 125 wRC+, and setting career highs with 35 home runs and 113 RBIs. His 6.8 WAR led catchers as well, leaving the next best catcher over two wins in his rear view. He went on to hit as well or better in the three years following, posting wRC+ marks of 149, 125, and 128, but injuries caused him to play 111 games or fewer in all of those seasons. Despite still being extremely valuable in abbreviated playing time, he was able to ink only a one-year deal with the Florida Marlins in his first trip to the open market, where he was able to show he was healthy again, leading the Fish to a World Series title.

This time around, Boras was able to help him cash in, putting together a four-year pact with the Detroit Tigers — a team thathad  just finished a historic 119-loss season. Rodriguez would not only continue to be extremely valuable, but surprisingly durable, playing in at least 129 games per season. As he was a 32-year-old catcher with a lot of innings behind the dish, though, he declined steadily throughout the life of the contract, posting WAR totals of 4.7, 3.2, 2.8 and 1.5. Though he was a still above average defender, he was only an above-average hitter once, when he produced a 134 wRC+ in 2004 — the first year of the deal. The Tigers would pick up his $13 million option for the 2008 season, making the total contract value worth north of $50 million, but would trade him to the Yankees later that summer.

A Hardball Times Update
Goodbye for now.

First Base: Mark Teixeira– New York Yankees

Eight years, $180 million
Best season: 2009- 142 wRC+, 5.2 WAR
Total WAR: 18.1

When Teixeira became the highest paid first baseman in the game, he was certainly one of the best first baseman in the game. In his six seasons prior to free agency (2003-08), only Lance Berkman and Albert Pujols were more valuable. The last two years of that span were especially great, as his 149 wRC+ was tied for sixth best in all of baseball. Still just 28 and a free agent, Teixeira owned a career slash line of.290/.378/.541 and had already tallied 26.7 WAR. Because of that, the Yankees decided to make him the third highest player on their team.

Much like Rodriguez, Teixeira was  a moderately valuable player in his new contract. For the first three year, he was still among the top seven first baseman in baseball by WAR, averaged 156 games per season, and helped the Yankees win the World Series in 2009. Although his decline was less noticeable, it was still there, as his offensive output saw a three year decline during that same time span, posting wRC+ marks of 142, 128, and 124. By 2012, his body began to betray him on a regular basis, and he would never play more than 123 games in a season again. He did bounce back with a 143 wRC+ in 2015, but injuries derailed him again, forcing him into retirement the very next year.

Honorable Mention: Chris Davis- Baltimore Orioles
Seven years, $161 million

Second Base: Jose Altuve– Houston Astros

Five Years, $151 million
Best season: TBD
Total WAR: TBD

When Altuve emerged as the everyday second baseman for the Houston Astros in 2012, the team saw an opportunity to lock up its young star, signing him to a four-year deal buying him out his arbitration years, guaranteeing him $12 million. Even before he cemented himself into the game’s elite, that is quite a bargain of a deal. If you think that’s oddly low for a Boras deal, it’s because it wasn’t a Boras deal. Altuve actually left Boras, and then rejoined him to help negotiate the highest contract in Astros history after his MVP 2017 season. Though he still would’ve been under the old contract for the 2018 and ‘19 seasons via club options, the new deal guarantees him a cool $10 million per year and then $26 million a year from 2020-24 — his age 30-34 seasons.

Shortstop: Alex Rodriguez – Texas Rangers

10 years, $252 million
Best season: 2002- 158 wRC+, 10.0 WAR
Total WAR: 56.1

Let me first acknowledge the fact that the third baseman should come before the shortstop if this list followed baseball’s position numbers, but for the list to make both logical and chronological sense, I’ve opted to go this route instead.

A-Rod was third only to Barry Bonds and Jeff Bagwell in terms of WAR from 1996-2000. Hitting the open market after just his age-24 season (let’s appreciate that for a moment), he was primed to become baseball’s highest paid star, and with the help of agent Boras, that’s exactly what happened. The best of the Big Three generational shortstops, A-Rod would continue to put up Hall of Fame season after Hall of Fame season. When the Rangers failed to construct anything remotely resembling a winning product, they famously traded him to New York just three years in to his contract.

A-Rod would have to permanently move to third base as a Yankee, and would put up the two best offensive seasons of his career in the Bronx, with a 175 wRC+ in 2005 and a 174 mark in 2007 — both netting him American League MVP honors. It was after 2007 that Boras would advise him to opt out of his current pact, leaving three years and $72 million on the table. It wouldn’t be long before he’d sign his second record-breaking deal.

Third Base: Alex Rodriguez- New York Yankees

10 years, $275 million
Best season: 2008- 152 wRC+, 5.8 WAR
Total WAR: 22.3

When he opted out of his original deal and reached free agency, A-Rod intended to stay with the Yankees. The deal was criticized for obvious reasons, mainly that he was now entering his age-32 season, meaning 10 more years would carry him into his age-41 campaign. The deal also included milestone-based incentives, such as reaching the all-time home run record, that would raise the total value of the deal past the $300 million mark — which would have been a Boras milestone.

Neither would reach that milestone though, as A-Rod finished his career with 696 home runs, and Boras would have to look elsewhere for his $300 million man. A-Rod would continue to produce at the plate, but he was clearly not the same player. He put up only one season of at least 5.0 WAR, and the only year he played in more than 150 games was in 2015 after serving a 162-game suspension for using performance enhancing drugs. A year later, he would be done for good, as below replacement level production at age 40 forced him into retirement with a year left on his contract.

In total, A-Rod made roughly $384 million between his two deals. While A-Rod is not technically considered a ‘$300 million man,’ it’s worth noting that neither of the aforementioned Machado or Harper will make as much over their entire careers than he did in his 15 years with the Rangers and Yankees; only Trout will out earn A-Rod in pure baseball dollars.

Left Field: Jayson Werth– Washington Nationals

Seven years, $126 million
Best season: 2014- 141 wRC+, 5.3 WAR
Total WAR: 14.3

The late 2000s and early 2010s may have been the best time to be a free agent in baseball history. Many teams still hadn’t embraced a sabermetric economic model in their front offices, and players were still thought to be entering their prime in their early 30s. Perhaps there is little better anecdotal evidence of this than Jayson Werth.

The Nationals had just drafted phenoms Stephen Strasburg and Bryce Harper with first overall picks in back-to-back drafts, and were ready to make a big splash in the free agent market. Werth, coming off a four-year run as a major player in a stacked Phillies core, seemed to be the perfect fit. He hired Boras in the 2010 offseason, and just three months later, the Nats made the 32-year-old the third richest outfielder in baseball behind Manny Ramirez and Alfonso Soriano.

Like other 30-something signees on this list, he had a few good years, specifically in 2013-14 when he posted WAR totals of 4.4 and 5.3, respectively. Other than that, though, injuries and age ultimately kept him from ever getting back into baseball’s upper echelon. Outside of those two great years, Werth had only one other season of 2.0 WAR or better.

Honorable Mention: Matt Holliday– St. Louis Cardinals
Seven years, $120 million

Center Field: Jacoby Ellsbury– New York Yankees

Seven years, $153 million
Best season: 2014- 109 wRC+, 3.5 WAR
Total WAR: 7.9 (two years remaining)

Ellsbury should’ve won the MVP in 2011. In his Brady Anderson-esque year, he set career highs in home runs (32), RBIs (105), runs scored (115), and wRC+ (150), all the while playing great defense in center field, pacing the league with 9.4 WAR. To that point, he had never hit more than nine long balls at any level of professional baseball. In his 2013 walk year, he was still valuable, producing a 112 wRC+ and 4.6 WAR, but swatted only nine homers, tying his non-outlier career high.

When he hit free agency after his age 29 season, there were concerns about his health, as well as his ability to reproduce another season of 2011’s caliber. It’s hard to say whether the Yankees were in fact chasing Ellsbury’s 2011 dragon, they were okay with what he was outside of that, or if they were just motivated to take him away from the Red Sox a la Johnny Damon (also a Boras client). Either way, the aforementioned concerns materialized. Injuries have kept him off the field for nearly half the life of the contract so far, including sitting out all of 2018.

Right Field: Bryce Harper- Philadelphia Phillies

13 years, $330 million
Best season: TBD
Total WAR: TBD

Since the age of 15 (and possibly younger), Harper has been in the public eye. Whether it was getting on the cover of Sports Illustrated, hitting 500-foot bombs in major league stadiums, or torching collegiate pitching (with a wooden bat) in what should’ve been his junior year of high school. Of course he was going to be a first overall draft pick. Of course he was going to make his major league debut at 19. Of course he was going to win an MVP award.

Of course Scott Boras would be be his agent. Of course he would sign a record deal.

Despite his ups and downs, Harper to this point owns a career 140 wRC+. In his best year, his aforementioned MVP season, he produced a 197 wRC+, and set career highs in both games played with 153 and home runs with 42, the latter of which still stands. It was the only season during which the Harper vs. Mike Trout debate was truly a debate, as Trout, as consistently great as he’s been, has never produced a mark that high. Though he hasn’t been quite as good since, he’s still among the game’s best hitters, still producing a 135 wRC+ in a “down” 2018 season. Like Alex Rodriguez, he enters his new deal with his best baseball theoretically in front of him. Unlike A-Rod, though, he has no opt-outs in his deal.

Designated Hitter: Prince Fielder– Detroit Tigers

Nine years, $214 million
Best season: 2012- 153 wRC+, 5.0 WAR
Total WAR: 7.4

Right after Boras’ record-setting arbitration settlement worth $15.5 million, he made Fielder the fourth highest paid player in baseball the following year, getting him a surprising deal nine years in length. It didn’t seem like a bad idea at the time — Fielder had just come off a 4.7 WAR season and produced a career wRC+ of 141 to that point. The idea of going to the American League presented the ability for the Tigers to use him as a DH as he aged (an idea fueled by conventional wisdom), cushioning the concern of having him under contract through his 36 season.

He would give the Tigers one All-Star caliber season in the first year of the deal and a slightly above average season right after, and then was dealt to the Texas Rangers, where back surgery would put an end to his mini iron-man streak of 547 consecutive games played. He would win Comeback Player of the Year in 2015, but suffered a career ending neck injury the next year, just five years into his contract.

Starting Pitcher: Max Scherzer– Washington Nationals

Seven years, $210 million
Best season: 2018- 2.53 ERA, 2.54 FIP, 7.2 WAR
Total WAR: 28.7 (Three years remaining)

In today’s game, the megadeal for a pitcher in his 30s has become an elusive one. As I’m writing this, Dallas Keuchel remains unemployed. Had Scherzer himself reached free agency after the likes of David Price and Zack Greinke (both of whom have performed respectably, if unspectacularly), one could imagine a world in which he gets a deal south of the one the Nationals gave him entering the 2015 season. In what has been Boras’s best deal in terms of return on investment to date, all Scherzer has been since then is the best pitcher in baseball.

Scherzer won the Cy Young award in both 2016 and 2017. He finished second in Cy Young voting in 2018, in what was arguably his best season of the three (it was his best in terms of WAR). It’s hard to imagine him declining anytime soon, as his fastball velocity has yet to see a significant dip, and his strikeout, walk, and home run numbers have gotten better relative to 2016 and ‘17. If free agents are indeed boat docks in the eyes of Boras, Scherzer is the port, and the Nationals were a cruise ship.

The 2018-19 offseason was the 20th America’s Cup. And just as we can celebrate the past 20 years, we can celebrate the next 20, as Boras has no shortage of clients who could top any of the players on this list. Some of these players may reach free agency; some may choose to sign extensions, but any or all of these them could insert themselves into this exclusive club.

2020: Gerrit Cole (SP), Xander Bogaerts (SS), Marcell Ozuna (LF)

2021: Jackie Bradley Jr. (CF), Aaron Sanchez (SP)

2022: Kris Bryant (3B), Michael Conforto (LF), Lance McCullers, Jr. (SP), Corey Seager (SS)

2023: America’s Cup cancelled

2024: Cody Bellinger (1B, CF), Matt Chapman (3B), Rhys Hoskins (1B), Julio Urias (SP)

2025: Juan Soto (LF)

2026: Fernando Tatis  Jr. (SS)

As surely as teams will continue to try to punch their ticket to Playoff-Ville, Boras will continue to be the conductor. And as long as he continues to have passengers, we as fans can count on the evolution of the All Scott Boras Contract Team. While Harper’s place in the record books was short-lived, so will Boras’ stay in second place.

Brian Menendez is a senior writer for DRaysBay of SBNation. He lives in Atlanta, Georgia, where he is the star pitcher of his local men's baseball league. You can find him on Twitter as @briantalksbsb.
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4 years ago

Are you assuming that Fernando Tatis Jr will leave Dan Lozano?

4 years ago

Thanks for doing this. We all have our perceptions but reviewing the list is helpful to challenge and/or confirm those assumptions. From a team perspective the list can be described as “the Good, the Bad and the Ugly”. Reason to think there is excess value (Pudge, AROD I) in mega deals and plenty of pause for concern (Jacoby Ellsbury, Prince Fielder, AROD II). Good insight.

Dave T
4 years ago

Machado and Harper are not the first $300 million contracts in baseball. Stanton signed an extension for 13/$325 million 2014.

Dave T
4 years ago
Reply to  Dave T

*in 2014

4 years ago

Very interesting, entertaining and well-written. Thank you!

4 years ago

Myself, tho’, I think Boras has clearly peaked. In part because his marks are mostly gone. There’ll always be a few egomaniacal owners for him to personally fleece, but the 4 biggest $$$$ clubs – Yankees, Red Sox, Dodgers + Cubs – all appear to be thoroughly inoculated.