top of page
Playing Poker

Free Agent Lottery - AKA Betting on Yourself 

There’s a point in which a player makes it as a bona fide major league player who is going to be in the big leagues for a while and at that point a franchise is going to realise he’s not going to extend on the cheap, he is either going to get a lot of money to stay on the team or he is going to test free agency to get the possible deal available for him. The argument is a test of risk for both the team and the player. For the player its shall I take a less amount of guaranteed money now in case I don’t become the player I think I will, or for the team am I going to get a good deal and get a player on a great contract or be stuck with a deal weighing the franchise down on a player who is not justifying the contract.

Welcome to the free agent lottery.

It’s never been a better time to be a free agent the key element of this all however is that is only as long as there is a team that is willing to sign you, starting pitching for example is at a premium and we have already had examples of players getting a contract based on their position as opposed to their talent.


Lets look at Frankie Montas a pitcher who when healthy is a great option for the middle to end of a rotation but last season he did not show that. In the final year of his Yankees contract he earned $5.025million and was restricted through injury to 1 appearance against the Kansas City Royals on October 1st pitching 1.1innings he had 2 hits but didn’t allow a run giving him a season ERA of 0.00. Obviously that’s irrelevant but during his tenure Montas has not become a better pitcher than what the Yankees thought they were getting when they traded for him mid-season 2022. Montas’s 26 pitches he threw however must have done something right as on Jan 2nd 2024 he signed a one year $14million dollar deal with the Cincinnati Reds which includes an additional $20million option mutually for 2025.Again this isn’t a dig at Montas but it does illustrate how free agency for him has come at a perfect time. I always say position players win games pitchers win championships and free agency has come up trumps for Montas on this occasion and the 1.1 innings pitched was always more about showing teams he was healthy than helping the Yankees out on that day.


Teams will always want to keep their pay structure under as much control as possible for additional flexibility when it comes to adding players or restructuring mid-season to help a playoff bid. The Atlanta Braves have taken to securing long term deals for a lot of players still under team control to get them at a premium before they hit their full value and potential. In recent years they have signed players such as Austin Riley, Matt Olsen and Sean Murphy on long term extensions before they approached free agency and are seen as the benchmark of how to keep a core group together without navigating the superstar contracts by searching just the players hitting free agency every offseason.


This previous offseason the Milwaukee Brewers did something almost unprecedented when signing outfielder Jackson Chourio to an 8 year $82million deal with club options for the 9th and 10th year. This is the largest contract ever given to a player yet to make his major league debut. He has since come up and started the season slowly. However, this is clearly an investment to secure a player and keep a team control contract where if the player reaches the potential the Brewers think he will it will work out to be a great deal. Will this soon become a more common thing to tie up the assets before they hit a larger market potential.


Then we look at the Scott Boras the perceived super-agent the man who does everything in his power to make sure his clients always hit free agency (Jose Altuve extending for the Astros was a rare occasion of this not being the case but this was driven more by Altuve’s desire to not test free agency and determination to play in Houston for the rest of his career). The perception is in general that if a player makes it to free agency and backs this up with a great free agency year the offers the payer will receive what will be tantamount to generational money. Arguably the 2 Scott Boris clients we were expecting to get the biggest contracts in the offseason were Jordan Montgomery who was an absolute stud in the offseason being a massive part of the Texas Rangers first World Series title last year and Blake Snell coming off a second NL Cy Young award.


Last season’s off season free agency merry-go-round didn’t really get going at the usual pace last year mainly due to waiting on where the billion dollar duo of Shohei Ohtani and Yoshinobu Yamamoto would end up signing. Montgomery ended up going to the Diamondbacks on a 1 year $25 million dollar contract with a vesting player option of $20 million dollars for 2025 and Snell ending up signing for the Giants on a $62 million dollar deal with a player opt out after 2024. Does this now signal the wings of change are starting. Perhaps? The Dodgers spent over a billion dollars on two players, but Snell and Montgomery signed deals which were overall much less than they were expecting. Since his move Montgomery has even left Scott Boras indicating he wasn’t happy with the deal he ended up signing this season.


On the eve of the 2022 season the New York Yankees Brian Cashman offered Aaron Judge $17 million in arbitration and a 7-year extension of $213.5 million (so a total of $230.5 across 8 years meaning the 7 year extension would have been an AAV (annual average value basically how much each year’s salary breaks down to) of $30.5 million a year. Judge then proceeded to have one of the best single seasons in baseball history breaking the AL home run record by recording 62 home runs. Judge put himself in the position where he pretty much guaranteed additional money the Yankees simply had to sign judge when he hit free agency and he ended up signing for 9 years for $360 million increasing the AAV to $40 million.Judge gambled on himself and won getting himself an extra $146 million. Scott Boras always gambles on free agency and it could be argued that this has cost him and more specifically his clients in overall guaranteed money.


There is no denying both Montgomery and Snell are great pitchers it would be hard to see how winning between them a world series and a second Cy Young could really be matched. Also let’s factor in the time lost both players missed the start of spring training and therefore the start of the regular season. In Snell’s case his Cy Young years are great but he doesn’t provide an amazing total amount of innings and his non Cy Young years represent different levels of performance in these seasons. The time to get the mega money could arguably have passed. Every case and every player will be a different scenario but with pitchers never being paid more in the history of the sport could it be argued that the guaranteed money could be the place for players to look at when offered going forward.


When a player is earning a potential contract of say $200 million how much more money can you spend as a human. Is it an ego thing where a player wants to be paid the most and wants this to reflect in a sign of status. What can’t be denied though is in the world of professional sports where such high stakes can be over with one injury it’s a gamble based on a calculated risk of probabilities.

bottom of page