Two Former Yankees Alumni Chase Comeback Dreams In Their 40s
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Home News Ex-Yankees

Two ex-Yankees veterans in their 40s are making comebacks

Inna Zeyger by Inna Zeyger
May 20, 2025
in Ex-Yankees, News
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Former Yankees pitchers Rich Hill and David Robertson.
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In an era dominated by fresh-faced phenoms and velocity-obsessed front offices, two seasoned veterans with Yankees pedigrees are challenging baseball’s youth movement by pursuing late-career comebacks.

Rich Hill, now 45, and David Robertson, 40, are proving that baseball careers need not follow conventional timelines. Both former Bronx hurlers are positioning themselves for potential 2025 returns, with Hill recently securing a minor league contract with Kansas City and Robertson emerging as a possible solution for Philadelphia’s suddenly depleted bullpen.

Their journeys represent a powerful counternarrative in today’s game: experience, adaptability, and competitive fire still matter – perhaps now more than ever.

Rich Hill: The Curveball craftsman keeps going

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Eleven years have passed since Rich Hill‘s brief but effective Yankees tenure, where the southpaw posted an impressive 1.69 ERA across 14 relief appearances during the 2014 season. Since that pinstriped chapter, the Massachusetts native has transformed himself into baseball’s quintessential journeyman, with a passport stamped by nearly every corner of the major league map.

His recent agreement with Kansas City could potentially make history. Should Hill reach the Royals’ major league roster, he’ll match Edwin Jackson’s all-time record by representing his 14th different MLB franchise – a testament to both his longevity and continuous reinvention.

Currently assigned to Kansas City’s complex league in Arizona, Hill’s path back to the big leagues begins with fundamentals rather than fanfare. According to MLB.com reports, a promotion to Triple-A Omaha remains possible should his performance warrant advancement.

“He had been throwing, said he felt good,” Royals assistant general manager Scott Sharp told MLB.com when discussing the signing. “We reached out and said, ‘Hey, we’ve got a Triple-A opportunity. No guarantees, but if you want to pitch, this is the spot.”

Hill’s professional journey, which began with his 2005 MLB debut, represents a remarkable case study in persistence. Having maintained his big-league relevance in every subsequent season, he’s compiled 1,409 innings with a career 4.01 ERA while striking out 1,428 batters – all while relying increasingly on his trademark sweeping curveball as velocity naturally diminished with age.

Though his Yankees stint represents merely a brief passage in his baseball odyssey, Hill’s continued pursuit exemplifies how specialized skill sets and veteran savvy can extend careers well beyond conventional expectations.

Robertson: Phillies eyeing familiar bullpen presence

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While Hill begins his comeback journey in developmental ranks, David Robertson‘s return path might offer a more direct route to major league relevance.

Following a productive 2024 campaign with Texas that saw him compile a 3.00 ERA across 68 appearances, Robertson surprisingly remained without a team entering 2025. That situation appears poised to change following recent developments in Philadelphia.

With Phillies reliever Jose Alvarado facing an 80-game suspension and postseason ineligibility due to a performance-enhancing substance violation, the club has reportedly initiated contact with Robertson, according to Mark Feinsand of MLB.com.

The potential reunion makes intuitive sense. Robertson played a crucial role during Philadelphia’s unexpected 2022 World Series run, delivering a 2.70 ERA across 22 high-leverage appearances and solidifying the back end of their bullpen during October’s pressure cooker.

“Dave [Dombrowski] has a strong track record of using his resources to solve his near-term needs,” one National League executive told MLB.com anonymously. “One would expect that pattern to continue.”

Though Robertson’s initial Philadelphia tenure in 2019 ended prematurely due to injury concerns, his subsequent renaissance – first with the Phillies in 2022 and then with Texas last season – has reestablished his credentials. Even at 40, he remains among the most dependable relief options currently available, capable of immediate contributions to a contending roster.

Bronx bonds: Different eras, lasting impacts

The pair represents distinctly different Yankees eras, yet both left meaningful impressions during their time in pinstripes.

Hill’s Yankees chapter was brief but valuable, providing stability from the left side during a 2014 campaign marked by rotation uncertainty. His subsequent career renaissance spanned numerous organizations, including Boston, Los Angeles, Tampa Bay, Minnesota, and Chicago, establishing him as a rare case of a pitcher who refined his approach with age.

Robertson, conversely, represents authentic Yankee development. Selected in the 2006 draft, he debuted in 2008 and evolved into one of the organization’s most dependable bullpen assets throughout the early 2010s. His Yankees statistics – a 2.81 ERA over seven seasons with 524 strikeouts across 393 innings – place him among the franchise’s most reliable relief pitchers. His precise cutter and composure under duress earned him the “Houdini” moniker for his remarkable escape artistry in difficult situations.

For Yankees supporters, these resurfacing names evoke distinct franchise periods – from Hill’s journeyman contribution to Robertson’s signature high-leverage dominance.

Age-defying value in modern baseball

Today’s MLB landscape rewards youth, velocity, and cost control. Yet seasoned veterans with specialized tools maintain relevance, particularly for contenders like Philadelphia and developing organizations like Kansas City seeking depth.

While Hill can’t match young fireballers in radar readings, his curveball remains exceptionally effective, especially in controlled situations. Should he return to major league action, he’ll join rarified company with Nolan Ryan and Bartolo Colón among the modern era’s eldest mound presences.

Robertson, meanwhile, represents an immediate upgrade for multiple bullpens. Despite slight declines in his 2024 metrics, his command and strikeout-to-walk ratio still registered comfortably above league averages.

Pursuing twilight glory

In a profession where prime years typically expire before age 30, Hill and Robertson embody baseball’s resilient exceptions – competitors who adapt, persist, and continually pursue competitive excellence.

Whether these latest comeback attempts succeed remains uncertain. Yet for Yankees faithful and baseball purists alike, there’s an undeniable appreciation for watching these craftsmen attempt one more climb.

What do you think? Leave your comment below.

Tags: rich hilldavid robertsonex-yankees
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Inna Zeyger

Inna Zeyger

Inna Zeyger is a staff writer for PinstripesNation contributing to breaking news stories as they happen. Being at the stadium for Jeter's last game

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