Scott Boras wins his bets more often than not

In recent years, Scott Boras has often signed clients to short contracts when they deserved big ones. When he doesn't get what he wants, he signs at a high short-term price to break the bank later.

And he's been doing it for a long time. #AdrianBeltreInBoston

In the last few years, it's happened seven times that he's told a big client to sign short term to break the bank later. And let's just say his batting average is pretty good.

In fact, six of his clients have won their bets. The most recent example is Cody Bellinger, who has secured $222.5 million over seven years since signing his three-year contract two years ago.

I have to say, for the most part these short-term deals with opt-outs have worked out tremendously for Boras' clients. Combined short deal + long deal:

Snell – 6/$214M
Alonso – 6/$185M
Chapman – 7/$167M
Bregman – 6/$205M (NPV)
Rodon – 7/$183.5M

Bellinger – TBD

Montgomery – Fail

– Joshua (@JoshuaHowsam) January 11, 2026

Blake Snell, Alex Bregman, and Carlos Rodon moved twice in the process. Pete Alonso stayed in New York and then left, while Matt Chapman and Bellinger stayed with their teams when they got out of their small contracts.

Jordan Montgomery, meanwhile, was so angry at having to sign on short notice that he fired Boras. He then pitched poorly and injured himself, making his small contract a disaster.

These are the risks of such a deal.

But for the rest, the agent's stars all made good money. And when you hire an agent like Boras, you know exactly what you're getting into next: you risk signing several contracts.

We'll see how these deals age over time, but it's pretty interesting to see how free agency worked out for the top position players:

Tucker: 4/$240M

Bregman: 5/$175M
Bellinger: 5/$162.5M
Alonso: 5/$155M
Schwarber: 5/$150M

Bichette: 3/$126M

– Brandon Wile (@Brandon_N_Wile) January 21, 2026

This content was created with the help of AI.