The Winter Meetings are going on right now, and, despite that Twitter seems to have exploded with hot stove rumors, the chances of anything really huge happening are pretty slim. A three-way trade here or a too-high contract offer to John Lackey there is pretty much all we can hope to expect. One thing we know for sure, though, is that we won’t be seeing any record contracts being dealt out in Indy this week. In fact, it’s been a long time since we last heard the words “the new highest paid player in baseball”. It was nine years ago Thursday, when Tom Hicks (yes, the same Tom Hicks who has piled the Rangers under mountains of debt) signed Alex Rodriguez to the richest contract in sports history, totalling 10 years and $252 million. Since then, we’ve had a few different players take the mantle of “2nd Highest Paid Player” (and we’ve even had A-Rod outdo himself), but no one has yet been able to de-throne the Yankees’ third baseman from his place on high. And it’s not looking like anyone will in the near future. Which makes it a perfect time to look back at the history of the highest paid player in baseball. Using newspaper accounts of the signings, and my rough knowledge/recollections, I was able to trace back the title of “highest paid player” in baseball all the way back to Nolan Ryan’s 4 year, $4 million contract signed in the winter of 1979. For example, when Mike Piazza signed his then-record seven-year, $91 million contract with the Mets on Oct 26, 1998, the New York Times article announcing the signing said this: “Piazza surpassed pitcher Pedro Martinez of the Boston Red Sox, who last December signed a six-year contract averaging $12.5 million a year, as the highest-paid player in baseball history.” If I then went back to the article announcing Pedro’s contract signing, it would tell me that Greg Maddux and Barry Bonds were the last two players to hold the title, and so on. While this proved a little tricky, especially in the mid-80s, when the press hadn’t decided on a good standard for judging contacts, etc., I was able to fill in all the gaps. And by “all the gaps”, I mean every single player who, at the time of their contract signing, was considered the highest paid player in baseball – even if it was for only a day or two. So, the three days that Rickey Henderson was at the top of the charts in late-1989, or the two days that Mike Hampton owned the largest total contract ever, are accounted for here. There are a few caveats before I get to the list: For the list, I only considered the player whose average annual salary over the life of his contract was the highest at the time of signing. Just because the Twins gave Gary Gaetti some weird three year contract in 1989 that allowed him to choose how much of his total four million he got paid each year doesn’t mean that we should consider him the highest paid player in baseball. The same with Dan Quisenberry and his odd real-estate deal he signed with the Royals that made his earnings for 1989 almost $3 million. This also means that ridiculously backloaded contracts do not knock someone off the list just because their average annual salary is less than the salary the backloaded player earned that year. If I had to go into those nuances, then I’d be facing something like this every season.

I’ve tried to use the terms at the time they were signed as the value of the contract. Ryne Sandberg, for example, signed a four-year, $28.4 million contract ($7.1mil/yr) in 1992, but retired before the contract ended. If we adjusted for the money he actually earned, his average annual salary would drop below $7 million. But that wouldn’t accurately reflect the baseball world as of 1992, so I did not make those adjustments.

I also tried to track the highest total contract value as it was broken. This usually went hand-in-hand with the highest average annual salary, but not always. Mike Hampton’s $123 million contract, for instance, was far and away the largest ever total package at the time it was signed, but his $15.3 million average annual salary was less than Carlos Delgado’s $17 million average annual salary. Hampton made my list, though, because the total package is newsworthy in itself.

Finally, while I made every effort to verify my completeness from Ryan to A-Rod, I suspect that I may have missed one or two players, especially there in the mid-80s. If anyone can show that I skipped over someone who, for however briefly, was the highest paid player in baseball by average annual salary, please let me know. I’d be happy to include them. That should be it for the caveats. On to the list! (click “Read More” to continue reading) A Timeline of the Highest Paid Player in Baseball 11/19/79: Nolan Ryan (Houston Astros), 3 years/$3.5 million, $1.17 million Average Annual Salary (AAS) [source]

The first $1 million-man, Ryan made great use of the new economic frontier when he went home to Texas in the winter of 1979. His total contract was for 4 years and $4.5 million (including bonus), but only the first three years were guaranteed. Those details weren’t all that important, though. Breaking the $1 million barrier was all that mattered.

12/15/80: Dave Winfield (New York Yankees), 10 years/$25 million, $2.5 million AAS [source]

1/26/81: Dave Winfield (New York Yankees), 10 years/$20-24 million, $2-2.4 million AAS [source]

Winfield’s contract was initially signed and announced in December 1980. The value was given at approximately $25 million – a base salary of about $1.6 million per year plus a cost-of-living adjustment each year not to exceed 10%. It didn’t take long for Steinbrenner to freak out, though, saying that he misunderstood the terms. The two parties later renegotiated the contract to drop the cost-of-living adjustment down some. I could never find a consensus value for the new contract. Some would refer to it as a $24 million contract, while some would say $20 million or $22 million. Since the exact value was hard to pinpoint, it was a little tough to determine if someone’s contract (like George Foster, Gary Carter, Mike Schmidt, Jim Rice, or Ozzie Smith) definitely exceeded Winfield’s. In the end, though, I stuck with Winfield because I could never convince myself that any of the other contracts were absolutely bigger than his. Winfield’s contract was initially signed and announced in December 1980. The value was given at approximately $25 million – a base salary of about $1.6 million per year plus a cost-of-living adjustment each year not to exceed 10%. It didn’t take long for Steinbrenner to freak out, though, saying that he misunderstood the terms. The two parties later renegotiated the contract to drop the cost-of-living adjustment down some. I could never find a consensus value for the new contract. Some would refer to it as a $24 million contract, while some would say $20 million or $22 million. Since the exact value was hard to pinpoint, it was a little tough to determine if someone’s contract (like George Foster, Gary Carter, Mike Schmidt, Jim Rice, or Ozzie Smith) definitely exceeded Winfield’s. In the end, though, I stuck with Winfield because I could never convince myself that any of the other contracts were absolutely bigger than his. 9/4/85: Eddie Murray (Baltimore Orioles), 5 years/$13.5 million, $2.7 million AAS [source]

Murray’s contract was either 5 yrs/$13mil or 5 yrs/$13.5mil, depending on if you included the signing bonus. I credit Murray with the extra $500,000, since that stays in step with how we value contracts today. Not that it mattered when compared to Winfield’s contract. Either way, Murray was earning the highest average annual salary by September 1985. 2/16/89: Orel Hershiser (Los Angeles Dodgers), 3 years/$7.9 million, $2.63 million AAS [source]

The exact total of Murray’s contract does matter here, though. Without the signing bonus, Hershiser squeaks into the lead, but falls slightly behind if it is included. Like I said, I tend to think Murray should still be ranked #1 here. I mostly include Hershiser to point out what happened that week. On February 8, Dwight Gooden signed a 3 yr/$6.7 million extension ($2.23 mil/yr). On February 15, Roger Clemens signed a 3 yr/$7.5 million extension ($2.5 mil/yr). The next day, February 16, Hershiser reached his agreement. It was a good week for the three pitchers.

**EDIT

4/19/89: Frank Viola (Minnesota Twins), 3 years/$7.9 million, $2.63 million AAS [source]

Reader martin_s pointed this out in the comments below. After winning the 1988 AL Cy Young, he entered into some contentious negotiations with the Twins. At one point, it was reported that he would be signing an $8+ million contract, and then he said that the negotiations were done for the year. In the end, he ended up signing a deal equal to Orel Hershiser’s, making the two 1988 Cy Young winners twin highest paid players.

11/17/89: Bret Saberhagen (Kansas City Royals), 3 years/$8.9 million, $2.97 million AAS [source]

On November 15, 1989, Bret Saberhagen won his second American League Cy Young award in convincing fashion. Two days later, the Royals rewarded him by making him the highest paid player in baseball. The title wouldn’t last very long… On November 15, 1989, Bret Saberhagen won his second American League Cy Young award in convincing fashion. Two days later, the Royals rewarded him by making him the highest paid player in baseball. The title wouldn’t last very long… 11/22/89: Kirby Puckett (Minnesota Twins), 3 years/$9 million, $3 million AAS

11/28/89: Rickey Henderson (Oakland A’s), 4 years/$12 million, $3 million AAS

12/1/89: Mark Langston (California Angels), 5 years/$16 million, $3.2 million AAS [source]

Five days later, the Twins bested the Royals by making Kirby Puckett the first $3 million man in baseball. Six days later, Rickey Henderson matched Puckett in average annual salary but also received an additional year on the contract. Three days after that, the Angels lured free agent Mark Langston to the Big A with a five year, $16 million contract. Owners were bursting at the seams that winter to spend their money. 12/11/89: Mark Davis (Kansas City Royals), 4 years/$13 million, $3.25 million AAS [source]

And it wasn’t over. Less than two weeks later, the Royals made another splash, this time signing the National League Cy Young winner, closer Mark Davis, to the newest “highest paying contract in baseball.” That’s right, the winter of 1989, the Kansas City Royals not only signed both reigning Cy Young winners, they signed them each to, what was at the time, the highest salary in baseball. Those were different times. 1/17/90: Dave Stewart (Oakland A’s), 2 years/$7 million, $3.5 million AAS [source]

1/22/90: Will Clark (San Francisco Giants), 4 years/$15 million, $3.75 million AAS [source]

The hot stove cooled down for a few weeks but, in mid-January 1990, the Bay Area heated it right back up. First, Oakland ace Dave Stewart signed a two-year extension that made him the highest paid player in baseball. Five days later, San Francisco’s slugging first baseman Will Clark bested him with a four-year, $15 million deal. 4/9/90: Don Mattingly (New York Yankees), 5 years/$19.3 million, $3.86 million AAS [source]

The Yankees got into the mess a few months later, as Opening Day approached, signing Mattingly to a five year contract. A good chart of high-value contracts at the time can be found here. 6/28/90: Jose Canseco (Oakland A’s), 5 years/$23.5 million, $4.7 million AAS [source]

But it was Canseco who broke the bank that season. His five year extension signed in the middle of the 1990 season gave him an average annual salary of $4.7 million, nearly $1 million-per-year more than Mattingly. 2/8/91: Roger Clemens (Boston Red Sox), 4 years/$21.521 million, $5.38 million AAS [source]

The following winter, Clemens became baseball’s first $5 million-man. At this point, most players whose contracts made them the highest paid player in baseball were players signing extensions with their old teams. That would change some in the ’90s. 12/2/91: Bobby Bonilla (New York Mets), 5 years/$29 million, $5.8 million AAS [source]

Bonilla, for example, left Barry Bonds and the Pirates for the Mets and their nearly $6 million/year deal. 3/2/92: Ryne Sandberg (Chicago Cubs), 4 years/$28.4 million, $7.1 million AAS [source]

Sandberg, of course, stayed on with the Cubs, but not until they made him the game’s first $7 million/year player. As I said earlier, he retired before the end of his contract, so he didn’t earn the full $28.4 million. Still, there was no way for anyone to know that at the time. 8/24/92: Cal Ripken, Jr. (Baltimore Orioles), 5 years/$32.5 million, $6.5 million AAS* [source]

For Cal’s 32nd birthday, the Orioles awarded him the largest total package in baseball history. By making the deal for five years, he sacrificed the title of “highest paid player in baseball”, but he did become the sport’s first $30 million-man. 12/6/92: Barry Bonds (San Francisco Giants), 6 years/$43.75 million, $7.29 million AAS [source]

Bonds broke through after he declared free agency from the Pirates in the winter of 1992. The three-time National League Most Valuable Player went home to San Francisco and the $43 million contract offered by new owner Peter Magowan. It would keep Bonds as the top paid player for a few years. 1/7/93: Cecil Fielder (Detroit Tigers), 5 years/$36 million, $7.2 million AAS [source]

Unless, of course, you follow the strange math on display here. Basically, the argument is that, considering the way a signing bonus is counted in the salary formula (including interest, etc.), Bonds’ $7,291,667 average annual salary drops below Fielder’s $7,200,000. It’s a nitpicky little argument, and not one I agree with, but I figured I’d include it here for the heck of it. 1/31/96: Ken Griffey, Jr. (Seattle Mariners), 4 years/$34 million, $8.5 million AAS [source]

One of the most memorable events in Seattle Mariners’ history happened in October 1995, when the Mariners squeaked passed the Yankees in Game 5 of the ALDS. Griffey, of course, played a key role in that fifth and deciding game. Four months later, the Mariners signed Kid Griffey to a four year contract that averaged out to $8.5 million per year, blowing Bonds and Fielder out of the water. 11/19/96: Albert Belle (Chicago White Sox), 5 years/$55 million, $11 million AAS [source]

But the biggest blow came that November, ten months later. Cleveland’s surly star, Albert “Don’t Call Me Joey or I’ll Run You Over” Belle tested the market and found a taker in the White Sox’s Jerry Reinsdorf. By the time the contract was signed, the $9 million/year and $10 million/year barriers had been blown past and Albert Belle was sitting pretty at $11 million/year. It was a huge leap forward. The Associated Press had a good table describing the state of players’ salaries at the time.

4/2/97: Gary Sheffield (Florida Marlins), 6 years/$61 million, $10.17 million AAS* [source]

As the 1997 season started, the still young Florida Marlins made a splash by inking Gary Sheffield to the biggest contract extension in history. The average salary did not beat Belle’s $11 million per year, but the total package of $61 million was the largest ever for a major leaguer. As the 1997 season started, the still young Florida Marlins made a splash by inking Gary Sheffield to the biggest contract extension in history. The average salary did not beat Belle’s $11 million per year, but the total package of $61 million was the largest ever for a major leaguer. 4/20/97: Barry Bonds (San Francisco Giants), 2 years/$22.9 million, $11.45 million AAS [source]

Bonds also signed a contract extension that April (apparently, teams were trying to beat the luxury tax by signing extensions after the season began). It was only a two-year extension this time, but it put Bonds back atop the salary boards at nearly $11.5 million per year. 8/10/97: Greg Maddux (Atlanta Braves), 5 years/$57.5 million, $11.5 million AAS [source]

That summer, the Braves made Greg Maddux the first pitcher in six years to be the highest paid player in baseball with a five-year extension. Maddux’s agent, Scott Boras, apparently made Maddux being the highest paid player in baseball an important part of the deal. “This deal doesn’t happen if there wasn’t a shortage of pitching,” he said. ”Our industry is starved for pitching.” 12/10/97: Pedro Martinez (Boston Red Sox), 6 years/$75 million, $12.5 million AAS [source]

And that was clearly evident two months later, when the Red Sox made Pedro Martinez the league’s first $12 million man. For the first time since the winter of 1989, two pitchers claimed the title of “highest paid player in baseball” consecutively. At least this time it was for two of the greatest pitchers ever, and not Mark Davis. 10/26/98: Mike Piazza (New York Mets), 7 years/$91 million, $13 million AAS [source]

Pedro reigned as baseball’s top earner for just about a year. In October 1998, Mike Piazza, who had been shuttled around the league that summer in anticipation of his free agency, cashed in with the Mets. His seven year deal made him baseball’s first $90 million man and it’s first $13 million/year player. The industry may have been starved for pitching, but that didn’t mean that Piazza wouldn’t get his payday. 11/25/98: Mo Vaughn (Anaheim Angels), 6 years/$80 million, $13.33 million AAS [source]

But maybe it was just that the industry was starved for immobile sluggers as well. Less than a month after Piazza signed his big contract, the Anaheim Angels of Anaheim topped it by signing Mo Vaughn away from the Red Sox. 12/12/98: Kevin Brown (Los Angeles Dodgers), 7 years/$105 million, $15 million AAS [source]

But neither of those are the deals that people remember from that winter. That honor belongs to the Los Angeles Dodgers, Scott Boras, and Kevin Brown, who worked together to make Brown baseball’s first $100 million man. (I wrote some more about this signing and Kevin Brown’s Dodgers debut earlier this year.) The seven-year, $105 million contract shocked just about everyone. 2/10/2000: Ken Griffey, Jr. (Cincinnati Reds), 9 years/$116.5 million, $12.94 million AAS* [source]

As the 2000 season approached, it became more and more apparent to everyone that the Mariners would not be able to keep Ken Griffey, Jr., at the end of the season. Which meant, of course, that Seattle would have to deal him somewhere. You don’t let someone as singularly great as Griffey walk-away, after all. Eventually, the Mariners and Reds agreed on a trade while the Reds and Griffey agreed on a deal. The numbers that they came up with surprised everyone in their reasonableness. Griffey did not top Brown’s $15 million average annual salary, though he did surpass him in the size of the total package. 8/11/2000: Roger Clemens (New York Yankees), 2 years/$30.9 million, $15.45 million AAS [source]

Roger Clemens and the Yankees agreed to one of the strangest contract extensions ever in the summer of 2000. The Yankees reported the deal as three years and $30.9 million, or $10.3 million per year. However, the terms of the deal guaranteed Clemens two years and the entire $30.9 million. That would imply, then, that, if Clemens were to have picked up that player option for the third year, he would’ve been working for free. Which makes you wonder if the Yankees thought we were all idiots that year. When you do the real math of two years and $30.9 million, you see that Clemens broke through as the league’s top paid player. 10/20/2000: Carlos Delgado (Toronto Blue Jays), 4 years/$68 million, $17 million AAS [source]

But it wouldn’t last long, of course. Not in the winter of 2000. Two months later, the Blue Jays and Carlos Delgado agreed to a four year contract extension that made the first baseman the highest paid player in the game at $17 million per year. But I don’t think people really remember Delgado’s time atop the board because of what happened six weeks later… 12/8/2000: Mike Hampton (Colorado Rockies), 8 years/$123 million, $15.38 million AAS* [source]

…when Mike Hampton parlayed two great years (in the *ahem* Astrodome and Shea Stadium) into the largest contract ever handed out. And it just happened to be with the Colorado Rockies. It’s still remembered as one of the craziest contracts ever, but it might be thought of even worse if it wasn’t for what happened two days later. 12/10/2000: Alex Rodriguez (Texas Rangers), 10 years/$252 million, $25.2 million AAS [source]

What do you say about A-Rod’s ten-year, $252 million contract? This was a 24-year old shortstop who could hit 40 home runs, bat .320, and play gold glove defense year-in-and-year-out entering free agency at the prime of his athletic abilities and at the peak of baseball’s money-crazy era. There was just no way that he was going to earn a modest contract. That said, Tom Hicks certainly played his hand poorly in the negotiations, bidding against himself at seemingly every turn. The $252 million is astounding not because of its sheer size but because it was $50-80 million more than anyone else seemed willing to offer. (Good chart.) 12/13/2007: Alex Rodriguez (New York Yankees), 10 years/$275 million, $27.5 million AAS [source]

It’s amazing, but, even seven years later, A-Rod still reigned as the highest paid player in baseball. It goes to show just how high Tom Hicks and Scott Boras set that bar back in the winter of 2000. It’s almost fitting, then, that the only person to top A-Rod’s $252 million deal is A-Rod himself, who went about doing it in the worst possible way (by interrupting the World Series to announce his free agency and then crawling back to the Steinbrenners weeks later). He did manage to extend the life of his contract and raise his average annual salary to a ridiculous $27.5 million a year, so it wasn’t for naught. If A-Rod can continue his home run hitting ways and march on past Mays, Aaron, Ruth, and Bonds, he’ll earn himself an additional $30 million. That is far from certain, though.

That’s it. Every player that I could find who held on to the title of “highest paid player in baseball” for even a day since Nolan Ryan signed the first $1 million-a-year contract in 1979 is included here. It might be a while still before we can add on to this list. In the meantime, though, it should serve as a pretty good look at how baseball has changed since the advent of free agency. Please feel free to let me know if I missed anyone.