Since Dave Dombrowski officially took over the reins as the president of baseball operations for the Philadelphia Phillies in December of 2020, he has had one main focus in mind. That has been to make the Phillies a winning ball club by giving them a chance to be legitimate contenders on a yearly basis.
To accomplish that, Dombrowski has often looked to secure elite and promising talent by offering up some bold free agent contracts during every offseason since his arrival in Philadelphia.
Over the past five years, the Phillies have done quite well recruiting and retaining impactful free agents to help the team to their current sustainable winning success. But at the same time, Dombrowski has also ended up giving out some questionable deals that have backfired big time when all was said and done.
Let's take a closer look at and rank the six most embarrassing Phillies free agent contracts handed out by the president of baseball operations that he likely wishes he could have back.
Ranking Dave Dombrowski’s 6 most embarrassing Phillies free agent contracts
No. 6: Didi Gregorius (2021, 2 years, $28 million)
After posting 20+ home runs and 70+ RBIs in three of his previous four seasons with the New York Yankees, Didi Gregorius joined the Phillies organization as a free agent on a one-year deal for the 2020 COVID-shortened season. He hit .284 with an .827 OPS, with 34 runs scored, 10 home runs and 40 RBIs over 60 games that year.
The Phillies appeared to have found their shortstop for the future as they quickly signed him for another two years at $28 million. Unfortunately, Gregorius was a shell of his former self during those two years. He hit below .210 with an OPS below .640, with just 14 home runs and 73 RBIs across the two seasons.
As a result, he didn't last the 2022 season as he was ultimately released in August of that year. In fact, by the end of 2023, Gregorius was out of MLB altogether at age 33, making his drastic drop-off a sad reminder of how tough the sport can be.
No. 5: Max Kepler (2025, 1 year, $10 million)
With the Phillies looking for an official solution to their outfield for the 2025 season, Dombrowski felt that they had found one in former Minnesota Twins slugger Max Kepler. By inking a one-year, $10 million deal, he was expected to fortify the Phillies’ offense and defense at the same time.
But rather than taking the everyday outfielder role and running with it, Kepler struggled coming out of the gate. He ended up as part of the outfield rotation in the second half.
In the end, he managed to hit only a dismal .216 with a .691 OPS, with 58 runs scored, 18 home runs and 52 RBIs in 127 games. Kepler made the postseason roster, but with two hits in just 15 plate appearances, his overall impact just wasn’t enough to help put the Phillies over the top.
No. 4: Jeurys Familia (2022, 1 year, $6 million)
Even at the time of the deal before the start of the 2022 MLB season, there were already some red flags for reliever Jeurys Familia. Despite being a former All-Star and dominant closer during his prime, he was coming off three straight seasons in which he had some command issues. He had posted an ERA above 3.70 and a WHIP above 1.40 from 2019 to 2021 with the rival New York Mets.
In addition, Phillies fans were skeptical of Familia coming with some baggage pertaining to his past domestic violence accusations. Nevertheless, Dombrowski gave him an opportunity but he didn’t take advantage of it. In fact, Familia ended up posting some of the worst numbers of his career with the Phillies.
In 38 appearances, he compiled an abysmal 6.09 ERA and 1.85 WHIP, giving up 23 earned runs with a whopping 48 hits, 15 walks and 33 strikeouts in 34 innings. It wasn’t surprising that Familia didn’t end up finishing the season in Philadelphia. After being released by the Phillies he pitched for the Red Sox and Athletics but was out of MLB by 2023.
No. 3: Whit Merrifield (2024, 1 year, $8 million)
Coming off a deep postseason run in 2023, the Phillies were looking to bolster their roster with three-time All-Star and two-time American League hits leader in veteran Whit Merrifield. His ability to play multiple positions all over the field along with a sound bat made him supposedly a valuable addition to the lineup.
However, Merrifield turned out to be a major disappointment, amassing a feeble .199 batting average and a .572 OPS, with 21 runs scored, three home runs and 11 RBIs in 53 games. Things got so bad that the Phillies released him halfway through July.
He ultimately joined the rival Atlanta Braves for the stretch run. In doing so, Merrifield nearly lent a hand in preventing Philadelphia from finishing atop the National League East division, and that would have been an even greater disaster than the signing itself.
No. 2: Jordan Romano (2025, 1 year, $8.5 million)
One of the worst free agent contracts the Phillies have handed out recently has to be the $8.5 million they gave reliever Jordan Romano. It's rare for a free agent to land a solid contract after a rough season like Romano had in 2024 with the Toronto Blue Jays. He posted a dreadful 6.59 ERA and 1.46 WHIP in 15 relief appearances before undergoing arthroscopic surgery for a right elbow impingement.
Despite the red flags, the Phillies bet on a bounce-back year in 2025 for the former All-Star. However, it was a disaster. Romano registered a career-worst 8.23 ERA with a 1.45 WHIP, giving up 39 earned runs in 42 2/3 innings over 49 appearances. Not only that, it forced Philadelphia to give up two top prospects to acquire Jhoan Duran at the trade deadline to rectify their closer situation.
No. 1: Taijuan Walker (2023, 4 years, $72 million)
Unlike the contracts that were limited to just one or two years of pain and agony, the four-year deal Dombrowski handed to starting pitcher Taijuan Walker has hurt a lot more, costing the Phillies a whopping $72 million. Had Walker delivered the goods, no one would have been complaining.
However, three straight seasons sporting a plus-4.00 ERA and a WHIP above 1.30 while yielding 20+ home runs each year sure weren't what Philadelphia signed up for when they inked the former All-Star. With his struggles, Walker has even spent time in the bullpen, making the $18 million AAV pitcher one of the priciest relievers in the entire league.
With one more year left on his contract, Walker has the opportunity to make amends in his final season. But based on what was observed in his previous three, especially in his horrendous 2024 campaign, it will be impossible for Walker to provide the full value of his contract by the end of it.