Andrew Benintendi and Eduardo Rodriguez were key pieces in the Boston Red Sox’s 2018 World Series run - Benintendi patrolling left field with poise and clutch at-bats, Rodriguez logging valuable innings from the mound. Fast forward to 2025, and their careers have taken a turn that no one in Boston would’ve seen coming back in those championship days.
On Monday, both players were named among MLB’s worst contract situations - not quite cracking the top 10, but still earning “honorable mention” status on a list of the league’s most underwater deals. It’s a tough look for two guys who once helped hoist a trophy at Fenway.
Let’s start with Benintendi. The White Sox outfielder signed the richest free-agent deal in franchise history before the 2023 season - a five-year pact that still has $32.2 million left on the books over the next two seasons.
But the production hasn’t come close to matching the payday. Despite hitting 20 home runs last year, his overall impact has been minimal.
His fWAR over the last three seasons? -0.3, -0.1, and 0.2. That’s not just underwhelming - it’s borderline invisible in terms of value.
For a player once seen as a cornerstone, those numbers raise real questions about what the White Sox are getting for their investment.
Rodriguez, now with the Arizona Diamondbacks, finds himself in a similar spot. After a strong 2023 campaign with the Tigers, expectations were high when he signed with Arizona in December of that year.
But through two seasons in the desert, the results have been lackluster at best. He’s posted ERAs of 5.04 and 5.02 - not disastrous, but certainly not what the D-backs were hoping for from a veteran lefty still owed $40 million over the next two years.
There’s also an innings-based incentive tied to the 2028 season, which adds another wrinkle to an already complicated financial picture.
It’s a far cry from where both players were just a few years ago.
Benintendi, the seventh overall pick in the 2015 MLB Draft, looked like a future All-Star early in his career. He finished second in AL Rookie of the Year voting in 2017, driving in 90 runs and hitting 20 homers - both still career highs.
In 2018, he was a key cog in Boston’s championship machine, swiping 21 bases, hitting 16 homers, and knocking in 87 runs. His blend of contact, speed, and defense made him a fan favorite and a core part of that title team.
Since being traded out of Boston in February 2021, Benintendi has bounced around - from Kansas City to the Yankees and now Chicago. But he hasn’t been able to recapture that early-career spark, and the numbers reflect it.
Rodriguez, meanwhile, was a steady presence in Boston’s rotation from 2015 to 2021. His best year came in 2019, when he went 19-6 with a 3.81 ERA and 213 strikeouts over 34 starts - good enough for sixth in the AL Cy Young voting. But his career hit a major speed bump in 2020 when he missed the entire season due to myocarditis, a heart condition that developed after a COVID-19 diagnosis.
He returned strong enough to earn a deal with the Tigers in late 2021, but consistency has been elusive since. Arizona took a chance on him after his bounce-back year in Detroit, but so far, the results haven’t justified the price tag.
Both Benintendi and Rodriguez are reminders of how quickly things can change in baseball. Just a few years removed from being World Series contributors, they’re now examples of contracts that haven’t panned out. Whether they can turn things around remains to be seen, but for now, their names are tied more to financial regret than postseason glory.