Long-term deals for free agents aren’t always wise investments

With one eye on the upcoming winter meetings and the other on the end of the Basic Agreement between owners and players, baseball executives are understandably wary of giving big contracts to veteran free agents.

Too many players once felt that miracle cures went sour so quickly in their new environment that they provided little or no return on their investment.

Ask any general manager and they’ll know about all the big stars who imploded due to unpredictable injuries or poor performance.

List of flops

The list of culprits is long – going back to the dawn of free choice in 1976.

In alphabetical order, they include Bobby Bonilla, Kevin Brown, Yoenis Cespedes, Carl Crawford, Chris Davis, Nick Esasky, Jacoby Ellsbury, Wayne Garland, Josh Hamilton, Mike Hampton, Jason Heyward, Anthony Rendon, Pablo Sandoval, Stephen Strasberg and Barry Zito.

They were all once solid players whose fortunes went south for various reasons after signing long-term, high-dollar deals – many of which included a guaranteed or no-trade clause.

Esasky was only 30 when he left the Boston Red Sox after a 30-home run season that also included 108 runs batted in. But the first baseman gave the Atlanta Braves, who signed him, just 35 at-bats over nine games — and not a single extra base hit or RBI. A victim of vertigo, he hit .171 and retired. The Braves received no return on their three-year, $5.7 million guaranteed contract.

Garland was the poster boy for underperforming pitchers. The first player to receive a ten-year contract, he moved from the Baltimore Orioles to the Cleveland club now known as the Guardians. His guaranteed contract required $2.3 million — big money in that first year of free agency — after a dozen teams drafted negotiating rights for him in the re-entry draft then in use. Garland got all that money after going 20-7 with a 2.67 earned run average for the ’76 Orioles, but that was the only winning season of his nine-year career. Plagued by injuries, he lost 19 times in the first year of his new contract and, like Esasky, was done at the age of 30.

Fast forward to 2019, when the Washington Nationals rode the bat of Anthony Rendon and the arm of Stephen Strasburg to the only world championship in team history.

Unable to afford either after hitting free agency, the Nats kept the pitcher, giving him the same seven-year, $245 million contract that Rendon received from the Los Angeles Angels. Strasburg threw 31 1/3 innings over three seasons and was done for good at 33. He won exactly one game before retiring with four years left on his contract.

After leading the National League with 126 RBIs in 2019, Rendon never played as many as 60 games in a season again. The Angels bought out the remainder of his contract after the 2025 season.

Rendon’s bloated pact, which has one year and $38 million remaining in its contract, represents about 25 percent of the Angels’ payroll of $166, according to Roster Resource. But it wasn’t as bad as Bobby Bonilla’s, which seems to have a half-life.

After suffering significant losses in the Bernie Madoff Ponzi scheme, Mets owners Fred and Jeff Wilpon renegotiated Bonilla’s contract – even though he had stopped playing for the team a year earlier.

So it was that the 2000 Mets bought out the $5.9 million still owed to Bonilla. At an annual interest rate of 8 percent, the team agreed to pay him $1.19 million from July 1 through 2035, when he would reach the ripe old age of 72. Another deferred dollar deal, which started in 2004, will pay him $500,000 a year through 2029.

Mets fans now “mark” Bobby Bonilla Day every July 1.

But wait, there’s more! According to ESPN, the Mets also have an obligation to pay Bret Saberhagen $250,000 per year for 25 years.

Another former Met, Max Scherzer, will still receive an annual stipend from the Washington Nationals until his deferred $105 million is paid in full through 2028. Never mind that he has pitched for a handful of other clubs since then.

Chris Davis also counts the money coming from his deferred contract. His $59 million deferment is spread over 15 years and runs through 2037. From 2026 through 2032, Davis will receive $3.5 million per year from the Baltimore Orioles, whose initial investment quickly went south.

Another former slugger, Manny Ramirez, still receives annual checks from the Boston Red Sox, although the cash flow will end in 2026 when his $24.2 million in deferred dollars ends.

Prices don’t help

Even award winners aren’t exempt from the malaise that plagues many free agent signings.

Zito, who had won a Cy Young with the Athletics, was essentially a scratch for San Francisco after signing a seven-year, $126 million pact to move across the Bay. And Hamilton, once American League MVP, was terrible in the wake of a five-year, $125 million contract that crashed when his rehab program collapsed.

Heyward got eight years and $125 million, but failed to score for the Cubs despite the cozy confines of Wrigley Field. Ditto for Crawford, whose seven-year, $145 million deal didn’t protect him from lingering injuries.

The curious case of Mike Hampton should also not be overlooked. Desperate for a big-name starter, the Rockies gave him eight years for $121 million, but quickly learned that Coors Field is often a pitcher’s graveyard as balls travel through the thin Alpine air — as Hampton proved when he hit seven home runs in one season.

Panda’s pact

Sandoval, the 2012 World Series MVP for San Francisco, earned five years and $95 million from the Red Sox but failed to capitalize on Fenway’s Green Monster.

The 2026 free agent class will almost certainly produce some hits and misses as well.

Now it’s up to owners, executives and agents to choose as carefully as the mom shopping for the holidays. As baseball history proves, appearances can be deceiving.