Long-Term Deals For Free Agents Aren’t Always Wise Investments

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

Too many players once considered panaceas soured so quickly in their new environs that they yielded little or no return on investment.

Ask any general manager and he’ll know about all the big-name stars who imploded because of unpredictable injuries or poor performance.

List of Flops

The list of culprits is long – and dates all the way back to the dawn of free agency 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.

All of them were solid players at one time whose fortunes went south for various reasons after they signed long-term, high-dollar deals – many of them guaranteed or containing no-trade clauses.

Esasky was just 30 when he left the Boston Red Sox after a 30-homer 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 a not a single extra-base hit or RBI. A victim of vertigo, he hit .171 and retired. The Braves got no return on their three-year, $5.7 million guaranteed contract.

Garland was the poster boy for poorly-performing pitchers. The first player to get a 10-year contract, he jumped from the Baltimore Orioles to the Cleveland club now known as the Guardians. His guaranteed contract called for $2.3 million – big bucks in that first year of free agency – after a dozen teams drafted negotiating rights to 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. Bedeviled by injuries, he lost 19 times in the first year of his new contract and, like Esasky, was done by age 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 both after they hit free agency, the Nats kept the pitcher, giving him the same seven-year, $245 million contract Rendon received from the Los Angeles Angels. Strasburg pitched 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 again played as many as 60 games in a season. The Angels bought out the remainder of his contract after the 2025 season.

Rendon’s inflated pact, which has one year and $38 million to go, represents some 25 per cent of the Angels’ $166 payroll, according to Roster Resource. But it was not 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 one year earlier.

So it was that the 2000 Mets bought out the $5.9 million still owed to Bonilla. Adding 8 per cent annual interest, the team agreed to pay him $1.19 million every July 1 through 2035, when he’ll hit the ripe old age of 72. Another deferred-dollars deal, which started in 2004, brings 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 a year for 25 years.

Another former Met, Max Scherzer, still gets annual stipends from the Washington Nationals until his deferred $105 million is paid in full through 2028. Little matter that he’s pitched for a handful of other clubs since.

Chris Davis is also counting the cash that comes in the wake of his deferred contract. His $59 million in deferments is spread over 15 years, continuing through 2037. From 2026-32, Davis will receive $3.5 million per annum from the Baltimore Orioles, whose initial investment went south in a hurry.

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

Awards Don’t Help

Even awards winners are not exempt from the malaise that marks many free agent signees.

Zito, who had won a Cy Young with the Athletics, was basically a zero for San Francisco after signing a seven-year, $126 million pact to move across the bay. And Hamilton, a one-time American League MVP, was awful in the wake of a five-year, $125 million contract that crashed when he his drug rehabilitation program collapsed.

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

The curious case of Mike Hampton can’t be overlooked either. Desperate for a big-name starter, the Rockies gave him eight years at $121 million but quickly learned that Coors Field is often a graveyard for pitchers because balls travel in the thin alpine air – as Hampton proved when he hit seven home runs in a single season.

Panda’s Pact

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

The free agent class of 2026 is virtually certain to produce its share of hits and misses as well.

Now it is up to the owners, executives, and agents to pick and choose as carefully as the mom shopping for holiday goodies. As baseball history proves, looks can be deceiving.