In baseball, the boldest financial move is sometimes the shortest contract.
Signing a one-year deal feels like a risk. But for some players, it was the calculated bet that unlocked hundreds of millions of dollars. These men trusted their talent, performed under pressure, and walked away with generational wealth.
The stories behind these contracts are as thrilling as any World Series moment. They prove that patience and self-belief, backed by elite performance, can be worth far more than any guaranteed long-term security.
Let’s take a closer look.
Adrián Beltré and the original pillow contract
Beltré did not invent the one-year prove-it deal, but he made it legendary.
Beltré signed a one-year deal worth $9 million with Boston in 2010 after a rough final year in Seattle. Agent Scott Boras called it a pillow contract, giving Beltré a fresh start in his career.
He responded brilliantly, hitting .321 with 28 home runs and a league-leading 49 doubles in one remarkable Boston season. That bold single-year effort then earned him a lucrative six-year deal worth $96 million from Texas.
Aaron Judge turns down $213 million and gets far more
The judge made the most profitable bet in baseball history by rejecting a contract offer most players would have signed immediately.
The Yankees offered Judge a seven-year extension worth $213.5 million just before the 2022 season started. He rejected it and played one year for $19 million through arbitration, putting his entire future on the line.
Judge hit 62 home runs and won the AL MVP award in a legendary season. He then re-signed with New York on a nine-year deal worth $360 million, gaining nearly $147 million more than he walked away from.
Cody Bellinger rebuilds everything in Chicago
The Dodgers gave up on Bellinger, but the Cubs gave him the fresh start he needed to remind baseball who he really was.
After two rough seasons in Los Angeles, Bellinger signed a one-year deal worth $17.5 million with Chicago for 2023. He was no longer considered an elite player or a reliable long-term investment for any team.
Bellinger hit .307 with 26 home runs and earned NL Comeback Player of the Year honors for 2023. He then signed a three-year deal worth $80 million and later a Yankees deal worth $162.5 million.
Carlos Correa opts out and upgrades his payday
Correa took a below-market deal, proved his worth in one dominant season, then exercised his exit clause and came back richer.
Correa signed a three-year deal worth just over $105 million with the Minnesota Twins in 2022 before opting out after one season. It was widely seen as below-market for a shortstop of his immense talent.
Deals with the Giants and Mets fell through before Minnesota signed him to a long-term extension. That new agreement paid Correa six years and $200 million, making it the biggest deal in the Twins franchise history.
Fun fact: Carlos Correa’s physical failed with two different teams in the same offseason. He still ended up with a $200 million deal just weeks later.
Kyle Tucker chooses record annual value over long-term security
Tucker skipped a decade-long offer and chose maximum dollars per year, proving that short-term thinking can be the most lucrative strategy.
Tucker spent one highly productive year with the Cubs after a blockbuster trade away from Houston in 2024. He entered free agency as the clear consensus top player available, drawing fierce interest from many contenders.
He picked four years at $240 million with the Dodgers over a much longer offer coming from Toronto. That short-term bet gave Tucker a record average annual value and opt-outs to re-enter the market early.
Marcus Semien silences doubters with one perfect season
Nobody expected Semien to transform a one-year deal into a seven-year contract, but that is exactly what happened in 2021.
Semien signed a one-year prove-it deal with the Toronto Blue Jays in 2021 after a very difficult previous campaign in Oakland. The deal was low risk for Toronto but a very career-defining chance for Semien.
He hit 45 home runs and put up elite offensive numbers in one of the finest second baseman seasons recorded. Texas rewarded him with a seven-year deal worth $175 million after that spectacular one-year showing.
Bryce Harper waits out team control and lands the biggest prize
Harper spent seven years being underpaid relative to his stardom before free agency finally gave him the market he deserved.
Harper spent seven full seasons in Washington under restrictive team-controlled deals that paid him far below what his talent deserved. He was a baseball superstar but had no real leverage until free agency finally arrived.
When he hit the open market after 2018, teams competed aggressively, and the bidding reached historic levels quickly. Harper signed a 13-year deal worth $330 million with Philadelphia, the richest free agent contract signed.
TL;DR
- Adrián Beltré popularized the ‘pillow contract’ strategy with a $9 million one-year deal in Boston that led to a $96 million Rangers contract.
- Aaron Judge turned down $213.5 million, delivered a legendary 62-homer season, and re-signed for $360 million with the Yankees.
- Cody Bellinger used a $17.5 million prove-it deal in Chicago to rebuild his career and eventually earn $162.5 million from the Yankees.
- Carlos Correa opted out of a three-year deal after one strong season and upgraded to a six-year $200 million Twins contract.
This article was made with AI assistance and human editing.
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