By Ed Botti
October 17, 2023
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Fans of the Yankees have become used to certain types of things. We all know our players will be booed mercilessly by fans in most opposing cities, they are usually the largest drawing road team in the league, they probably have the biggest celebrity band wagon in sports, they charge us a fortune to watch them play, the NY Media exaggerates any story involving a Yankee, and when they win the World Series they appear bigger than life on a worldwide basis.
We are all accustomed to it, and have made our peace with it. It is part of being a Yankee fan.
One thing we have become accustomed to lately and are not really at peace with is dishing out large valued contracts to players that are either past their prime, do not fit with the current makeup of the team, or are a walking injury waiting to happen.
Those are the contracts that infuriate the fans, especially when it appears that the athlete could care less what the fans think or say.
Large contracts are a problem in sports, and are only becoming more of a problem as the haves and haves not expand their presence in the league.
When 3 or 4 players on a team make more money than an entire other team combined, and the budget conscious team out performs the big spender year after year, it is not good for the game, and makes the decision makers appear foolish and inept.
Probably the most polarizing of current Yankee contracts is the deal Brian Cashman decided to trade for in the winter of 2017.
As a matter of background, On November 17, 2014 Giancarlo Stanton signed a 13 year contract for $325MM with the Miami Marlins. On December 9, 2017, the Miami Marlins traded Stanton, along with $30M, to the Yankees in exchange for 2B Starlin Castro and two prospects: 2B Jose Devers and RHP Jorge Guzman.
At the time Stanton, at 27 years old, had just finished his 3rd year under his 2015 contract, and the Yankees agreed to take on the remaining years of that contract:
$295M over the next 10 years, with a club option for year 11 at $25 million more.
I personally was not in favor of the deal from the minute I heard about it.
Why? First and foremost - Risk.
As a player grows older and past his prime (more often after age 27), his production starts to decrease. The older he gets, the more the falling-off accelerates.
As a player matures, most tend to get injured more often. It’s just an unfortunate fact of life. As they say, “youth is wasted on the young”.
And as these injuries add up, they impact a player’s ability to play at the same level, or even play at all.
Sound familiar?
I also looked at the opportunity costs associated with taking on 10 years for a soon to be 28 year old athlete. When a team designates a large portion of their budget to one player, it diminishes their ability to pay/acquire other players. The longer the contract term, the more this is a dilemma.
So when I analyzed Stanton’s long-term projections back in 2017, I saw a very productive 27 year old player coming off of an MVP season in Miami. But I also knew that his productivity and durability was going to decline more and more each year, tie up the team’s budget and resources for a decade, and clog up the lineup, despite what they may have said.
I also speculated if this was a knee jerk reaction to Cashman and the Yankees getting snubbed and rejected by Shohei Ohtani just two days earlier on December 7, 2017. I still firmly believe that was the case. One can only imagine how different things would have been if Ohtani chose the Yankees in December of 2017.
Had it been a five year deal, I probably would have looked at it differently, but 10 years? No thank you, Derek!
But of course, that is not what happened.
It did not take long at all for us to see the opportunity cost factor kick in. The following off season Bryce Harper, a one in a million player, left handed, aggressive, and openly campaigning to land in NY, was not even looked at.
Why? 10 years and $295MM was already committed to Stanton.
They didn’t even look at Manny Machado either.
When was the last time that two of the best young players in MLB became free agents, and the Yankees were not even involved?
Coincidence? No chance!
And they are paying for that dearly now.
Now, I may be in the minority here, but I do not blame Giancarlo one iota. He signed what he envisioned as his last contract to stay in Miami. He did not market himself to the Yankees, Dodgers, Mets, or anyone else. He was all set finishing his career as a lifetime Marlin. The Yankees are the ones that I blame. They sought him out. They worked the deal with Derek Jeter. Not Stanton. Yes, he did have a no trade clause and had to approve the trade, but he was not the person(s) that initiated the deal.
As we can now all see, it in fact did turned out to be a bad deal, and a deal that will continue to haunt this team for years to come.
Which got me thinking. Is this the worst deal in sports, or have there been others just as bad, or even worse?
Here are a few that have always stood out in my mind, in no particular order – excluding the obvious other terrible Yankee deals such as Ellsbury, Pavano, Rodon, Igawa, etc.…
Gilbert Arenas - Washington Wizards Six years, $111 million
The Wizards signed him away from the Golden State Warriors after the 2002/2003 season and had high expectations. However, the former All-Star was quickly sidelined with a knee injury. He would later receive an indefinite suspension for bringing firearms into the Wizards’ locker room.
Arenas himself recognizes it’s likely one of the worst deals in NBA history. The Wizards closed the books on him after they paid Arenas his final payment in 2017, seven years after he last played for them.
Albert Pujols- Los Angeles Angels, 10 years, $240 million
Pujols left St Louis to sign with the Angels in 2011 after a sure fire 11 year beginning to a hall of fame career. Prior to signing his mega contract, he had already accumulated over 400 home runs to go with a .328 career batting average and .420 on-base percentage.
The Angels were well aware that they were taking a huge risk by signing Pujols, who was entering his age-32 season, to a 10-year contract. They put their rose colored glasses on and did it anyway. It never paid off as Pujols’ on-base percentage nosedived, while his strikeouts skyrocketed. A bad combo!
Miguel Cabrera - Detroit Tigers, Eight years, $248 million
The Tigers signed their star first baseman to a long-term contract in 2016, after his 12 years of wreaking havoc on MLB pitchers. Cabrera earned MVP honors in 2012 and 2013, made 11 All-Star appearances and had a career .310 batting average. However, his performance quickly declined following his big payday.
Cabrera managed just 16 home runs in 529 plate appearances the year after signing his contract, later going on to miss much of the 2018 season due to hamstring and biceps injuries.
As the years unfolded, be continued his rapid decline, hitting 49 home runs over his final 6 years.
Photo by The Hockey News
Rick DiPietro – New York Islanders 15 years $67.5 Million
As I mentioned above, the simplest way to predict that a contract will turn into a bad business deal is for it to run for an extremely long time. Case in point, Goalie Rick DiPietro signed for an astounding 15 years at $67.5 million. He only played 50 games in his last 5 years before being bought out due to several injuries that prevented him from playing, resulting in a massive loss for the Isles.
Chris Davis- Baltimore Orioles 7 years $161 Million
Talk about a bad deal.
From 2012 to 2015, the all -star first baseman hit 159 home runs with a .256 batting average and .876 OPS. Not bad. But…
Following a trade to Baltimore in 2011 from Texas he hit 53 home runs and drove in 138 runs as he finished third in the MVP voting in 2013.While 2014 was a down year for him, he had a massive rebound in 2015 and signed his seven-year, $161 million contract.
In 2015, Davis hit .262, but his average plummeted to .211 in 2016 – the highest it would reach before he retired in August 2021.
His tenure in Baltimore was tarnished with strikeouts, slumps and an unbelievable 0-for-54 stretch.
He didn’t allow his contract to come to an end, retiring from MLB one year before its expiration in 2022.
Stephen Strasburg - Washington Nationals 7 years $245 Million
Highly touted for years and one of the better pitchers in the game…. when healthy. Strasburg had a dreamlike 2019 season. He led the league winning 18 games and throwing 209 innings and becoming MVP of the World Series, won by the Nationals.
He signed a 7 year $245 million contract following 2019. Since then, he has dealt with carpal tunnel surgery, thoracic outlet syndrome and other ailments and injuries.
As a result, he has pitched only 31 1/3 innings with a 1-4 record since signing the contract.
According to The Washington Post, it is unclear whether Strasburg will be able to pitch in 2024 – or ever again.
Anthony Rendon - Los Angeles Angels - 7 Years $245 Million
Talk about dodging another bullet by Washington GM Mike Rizzo, Stephen Strasburg’s World Series Champion teammate Anthony Rendon left Washington after 2019 for greener pastures and found agreeable partners in Angels’ Owner Artie Moreno, and Brian Cashman prodigy, GM Billy Eppler. Rendon finished 10th in AL MVP Award voting after the Covid shortened 2020 season, his first season after signing a free-agent deal with the Angels.
The former Washington Nationals star has played in just 143 of 486 regular season games over the last 3 seasons hitting 13 home runs and driving in a grand total of 80 runs while sporting a 3 year average of .236.
Say what you want about Billy, but he has learned well under the tutelage of Mr. Cashman!
Albert Haynesworth- Washington Redskins 7 years $100 Million
A talented NFL player when he secured a $100 million deal from Washington, only to play just 20 games and say thank you very much, I’m done!
Seemingly, it was Haynesworth’s plan all along to get paid and say “see ya”, which is probably why fellow former Redskin teammate Chris Cooley once called Haynesworth an “awful human being”. I can see why, Chris!
Ilya Kovalchuk – New Jersey Devils 15 years $100 Million
Similar to DiPietro, Kovalchuk received a contract that ran for a ridiculous 15 years for a reported $100 million. The deal alone landed the Devils in trouble with the NHL offices for breaching salary cap rules. It got even worse when Kovalchuk ditched the NHL to go and play back in Russia.
Mike Hampton – Colorado Rockies 8 years $121 Million
At the beginning of his career, Mike Hampton was decent lefty starter and won 22 games in 1999, but did he deserve an 8-year $121 million contract? After the 2000 Subway Series he was then signed to the biggest contract in sports history by the Colorado Rockies. Yes, he told us all it had nothing to do with money, and everything to do with the Denver School Districts being better than the New York School Districts (he actually used that as his reasoning!).
So what did he do after arriving in the Mile High City with a bundle of cash and registering his kids for school? In his two seasons in Denver, he went 21-28 and had an ERA of 5.75. The Rockies shipped him to the Florida Marlins, after which he was promptly traded 2 days later to Atlanta. His time on the Braves was largely marked by injuries as he had back-to-back Tommy John surgeries and missed two full seasons (2006 and 2007).
Amar’e Stoudemire – New York Knicks 5 years $99.5 Million
Due to a number of injuries with his knee, Stoudemire became a huge burden on the Knicks. He barely played at all throughout his tenure at MSG and eventually agreed to a buyout.
J.C. Jackson – Los Angeles Chargers 5 years $82.5 million
I would be remiss if I didn’t bring up this very recent deal. In 2022 Jackson left the New England Patriots and signed the big buck deal with the Charges. According to NFL.com sources, the cornerback refused to enter a game against the Raiders 2 weeks ago, even though one of his teammates, Michael Davis, got hurt.
His coaches could not convince the 27 year old millionaire to tie his shoes and enter the game, because he claimed he was not warm enough to play (I am not sure where he was during the team warmup prior to game). Apparently, this was not the first time this type of behavior was noticed by his bosses. The Chargers had enough and decided to cut bait and worked out deal with New England by swapping a couple of 2025 late round draft picks for the mercurial and unappreciative cornerback who (I guess) doesn’t understand that his employer agreed to a $ 82.5 million dollar contract in exchange for his services.
Photo by AP
Bobby Bonilla - New York Mets 5 years $29 Million
One of my all-time favorite deals. Bobby Bonilla was at one point the highest paid player in MLB via a 5 year $29 million contract the Mets gave him following the 1991 season. It gets worse. He didn’t live up to the contract, wore ear plugs at Shea Stadium and eventually threatened a New York beat reporter.
The crazy part came when the Mets had enough and wanted to cut ties with him, but they still owed him $5.9 million. Instead of buying him out and cutting him a check to go away, the Mets negotiated a new deal where he would instead be paid approximately $1 million a year, plus interest for 25 years. The deferred payments began in 2011, and will continue until 2035. The buyout will have cost them close to $30 million.
I am sure that our readers can add many more of these types of sports contracts to this list.
I suspect that the Zion Williamson’s 5 year $197 Million contract will make this list soon enough.
Investing big bucks and long term in a professional athlete is risky business for team owners because unlike a stock or a commodity, athletes are actually humans.
No one knows the future and players are paid for past performance.
According to a report by a large financial services group that caters to professional athletes, the average career span for a professional athlete is five years.
We all love Aaron Judge’s game, for sure. But, what will he be like from 2027-2031?
Ditto for Gerrit Cole?
Maybe they will be the outliers? Let’s hope so.
But, as we learned from Steve Cohen “Hope is not a strategy”.
There are certainly many types of matters and issues that can occur during an athlete’s career. Signing them to a long-term contract is a high risk that can hurt the franchise and restrict their ability to add players when a few are monopolizing a big portion of a budget.
I can count on one hand the number of long term contracts that ended up delivering what was anticipated.
For every Mike Mussina or CC Sabathia there are too many to name Carl Pavano(s) and Stephen Strasburg(s).
It seems as if every year, a longer more expensive contract is given to players. Major league sports owners and the leagues need to find a way to protect teams from these high-risk, no-reward contracts, before these financial encumbrances get worse (is that even possible?) and the fans ultimately are the ones paying for it!
Remember, 23 year old Juan Soto has already turned down a reported 15-year contract worth $440 million. He hit .275 in 2023, and he and his teammates are now golfing.
A base salary plus performance based incentives is the way to go. Why not? It works in almost every other industry on the face of the earth.
“New car, caviar, four star, daydream. Think I'll buy me a football team!"
RIP Dick Butkus
