MLB free agency: The 3 riskiest players set to receive massive contracts

Whenever MLB GMs set out to sign a player to a massive free agent contract, there is always quite a bit of risk involved. The risk is typically intensified as additional years are placed on that contract without opt-outs. The Angels contract that was tendered to Albert Pujols appeared to be a form of torture for everyone involved. It became abundantly clear that Pujols was not going to be the player the Angels had envisioned very early on, and they would be forced to endure that for many years.

Pujols is just one example from a lengthy list of free agency contracts reaping with regret. The main factors that typically define a contract as “risky” include: Health, degradation of performance, and fit with the team that signs them.

Teams aim to sign the players with the least amount of risk associated with them, but in order to build a contender you sometimes have to accept the risk in order to reap the reward. Heading into the World Series, I wrote how the Phillies were built upon a series of risky contracts that went their way. Kyle Schwarber and Bryce Harper could have been included in a list just like this in their respective year of free agency.

It’s not to say that these players will not work out for their teams, but there are many scenarios where the fan bases are ruing the day they were signed. Oddly enough, everyone included in this list is an absolute superstar, and all 3 of them are very likely to be in the hall of fame discussion.

As is Albert Pujols, but it doesn’t change the fact that he was handed an extremely risky contract that didn’t work out.

3. Justin Verlander

Justin Verlander is guaranteed to be entering the MLB Hall of Fame. He is arguably the best pitcher of the current generation and has 3 Cy Youngs to his name. In fact, he is negotiating a contract coming off of a Cy Young season, which is sure to drive his price way up.

Fangraph’s Ben Clemens estimates Verlander will receive a 2-year, $80 million contract. However, MLB.com’s Brian McTaggart wrote that Verlander and his agent are seeking a deal similar to that of Max Scherzer’s.

For what it’s worth, I personally question whether McTaggart can be trusted, considering he left Shohei Ohtani off of his AL Cy Young ballot. However, since he has the inside scoop with the Astros, we will assume this is correct.

Sherzer signed a 3-year, $130 million deal, which broke the record for highest average annual value on a contract at $43.33 million. If Justin’s contract comes anywhere near Sherzer’s, especially the 3 years, there is a ton or risk involved.

First off, Verlander will be 40 at the start of next season. At some point, human anatomy suggests the wheels have to come off. Whether its next year, or the years proceeding it, I have no way of knowing. I do know that I do not want to be paying that player $40+ million when that happens.

The other concerning part of this is how Verlander ended his season. He had a stellar start at the tail end of the World Series, but owned a 5.85 postseason ERA in 2022. It is an extremely small sample size, but it has to create some doubt that Verlander can return to his Cy Young form heading into next year.

1. Aaron Judge

I am probably going to get roasted like a stuffed pig at a luau for this one. Don’t worry, I am ready for it. New York Yankee fans are not known for lacking passion.

Aaron Judge had a pretty good season in case you are coming out of a coma. He hit a very large amount of home runs. In fact, he hit the seventh most all time in a single MLB season. Giancarlo Stanton, Ryan Howard, and Alex Rodriguez are all in the top 16 of that list. That holds relevance because every one of those players received an awful contract for the organization that signed them shortly after those seasons.

Am I saying that everyone who hits a lot of home runs is bound to bust? No, I am establishing precedence for them to receive contracts that they don’t live up to.

Clemens projects Judge to receive a 9-year, $315 Million contract, at a $35 Million AAV. That will put Judge at the doorstep of 40 years old, making $35 million.

Besides Judge’s first full season, and his most recent season, he has not exceeded a WAR of 5.5. Heading into 2019 Mike Trout received an extension similar to Judge’s projection, and he had 7 seasons with a WAR higher than 6.4.

Teams will be paying Judge to have numerous seasons of receiving top-3 MVP votes, and frankly, I don’t see that happening. My internal alarms start going off whenever a player doubles his average output in a contract season. There are success stories, but there are also very many failure stories.

The other layer of this is the fact that I expect Judge to exceed the projected contract. Since Clemens wrote his projections, the Dodgers have emerged as a potential suitor after not tending a contract to Cody Bellinger. Also of note, they do not have an alleged agreement to not pursue Judge as the Mets do.

Three teams that are sure to be in the Judge sweepstakes include the Yankees, Dodgers, and Giants. Those are three storied franchises with deep pockets. That is also not to mention the mystery MLB teams that always seem to pop up and make surprise bids.

I firmly believe there will be seasons in which Judge earns his salary, but I believe the seasons in which he doesn’t earn it will be much more plentiful.