Troy Tulowitzki and the Yankees: When destiny falters

If Derek Jeter was destined to be the Yankees’ shortstop, Troy Tulowitzki was destined to replace Jeter in the same position. It was written in the stars, baked into the kismet. Tulowitzki idolised Jeter growing up and modelled his game – all jump throws and timely hits – after The Captain. Tulowitzki wore #2 throughout his career in homage to Jeter, and was frequently linked to the Yankees in trade rumours. Tulo-to-the-Yankees became a recurring motif in baseball gossip columns – the poetic symmetry too romantic to ignore – and the mercurial shortstop lurked on the pinstriped radar for years as Jeter’s spiritual heir.

Alas, when conjecture morphed into reality and Tulowitzki finally became a Yankee – in 2019, years past his Colorado Rockies prime – he was a shell of his former self. By that point, Jeter had been retired for four seasons, and Tulowitzki was 34 years old, broken by myriad injuries that derailed his Hall of Fame trajectory. Long considered the ideal Jeter replacement, Tulowitzki played just five games in pinstripes. Even fate is fallible, you see. Even destiny sometimes falters.

However, a deeper look at the Tulowitzki-Yankees saga reveals a more nuanced story than is often acknowledged. Exploring that tale exposes the flaws of irrational extrapolation, and I’m keen to do so – freeing Tulowitzki from the scourge of hot take absolutism. Sure, he underperformed as a Yankee, but he was a Yankee, and that can never be expunged. Sometimes, we should celebrate such achievements, rather than litigating supposed failures, because Troy Tulowitzki has a unique place in Yankees history, and that should never be forgotten.

Was Troy Tulowitzki a childhood Yankees fan?

Troy Tulowitzki was born on 10 October 1984 in Santa Clara, California, into a family of Polish descent. Growing up in the southern Bay Area, young Troy was actually a diehard Oakland A’s fan, and his first baseball hero was Cal Ripken Jr., erstwhile shortstop of the Baltimore Orioles. Tulowitzki attended games at the Oakland Coliseum whenever Ripken and the Orioles came to town, and The Iron Man became a fitting role model as Troy developed into a tall shortstop with dynamic ability on both sides of the baseball.

To that end, Tulowitzki was preternaturally talented athletically. At Fremont High School in Sunnyvale, California, Tulowitzki was a prodigious basketball player, but his real passion lay on the baseball diamond. As a junior, Tulowitzki hit .536 while compiling a 15-1 record on the pitchers’ mound. His stock continued to rise through three fantastic seasons at California State University, Long Beach, leading Baseball America to consider Tulowitzki a top prospect by 2005.

Throughout his collegiate career, Tulowitzki actually wore #5 in tribute to Boston Red Sox icon Nomar Garciaparra, another epochal shortstop. It was a halcyon age for shortstops, as several young stars – Garciaparra, Jeter, Alex Rodriguez, Édgar Rentería – revolutionised the position in Ripken’s afterglow. Jeter’s iconic flip play against Oakland in the 2001 playoffs broke Tulowitzki’s heart, but the way Derek rewrote the laws of shortstop appealed to young Troy, who wove similar innovative flair into his approach.

Indeed, from an early age, Tulowitzki was laser-focused on becoming a big league shortstop and treading in the footsteps of his mould-shattering heroes. As an incessant reminder of that goal, Tulowitzki carried baseball cards of Jeter and Garciaparra in his back pocket during high school and college games. Troy was determined to replicate the performance and panache of those who carved a path for lean, offensive shortstops. Imitating the calm comportment of Jeter was particularly important to Tulowitzki, and Derek became the aspirational totem by which Troy measured progress.

Troy Tulowitzki idolised Yankees shortstop Derek Jeter and wore number 2 in tribute to The Captain 

The Rockies selected Tulowitzki seventh overall in the 2005 MLB draft and gave him a $2.3 million signing bonus to turn professional. A meteoric rise through the minor leagues saw Tulowitzki appear in the 2006 All-Star Futures Game, en route to an August 2006 big league callup. Tulowitzki gained valuable exposure in a promising Rockies lineup, and despite some early struggles, Troy won new fans across baseball with an exhilarating style of play. His gaudy potential seemed boundless.

Initially given the #14 jersey by Rockies management, Tulowitzki sought a change prior to his rookie season in 2007, eyeing the trademarked #2 of Jeter. In Colorado, #2 belonged to third base coach Mike Gallego, a former Yankees infielder. Incidentally, Gallego was the last Yankee to wear #2 before Jeter, and he knew the significance of single digits. While playing for Oakland in the late-1980s, Gallego refused to relinquish #9 when Reggie Jackson returned to the A’s, forcing Mr October into #44. Gallego did not surrender his Rockies #2 lightly, either, but Tulowitzki cited Jeter as inspiration and Gallego acquiesced.

Tulowitzki joined a phalanx of big leaguers – including Hanley Ramírez, BJ Upton and, later, Xander Bogaerts – who wore #2 in homage to Jeter. Meanwhile, Tulowitzki said the prospect of facing Jeter and the Yankees in a rare June interleague series motivated him to make the Rockies’ big league roster out of spring training in 2007 – which he did. Prior to the Yankees series at Coors Field, Tulowitzki bought bottles of Jeter’s cologne, Driven, for his teammates. Colorado then swept the three-game set as Tulowitzki went 5-for-9 with a home run. Sharing a field with Derek clearly brought out the best in Troy.

Brian Cashman wanted Troy Tulowitzki to replace Derek Jeter as Yankees shortstop

Tulowitzki produced one of the greatest rookie shortstop seasons in baseball history, hitting .291 with a .359 OBP, 24 home runs and 99 RBI. Tulowitzki dazzled defensively, too, often imitating Jeter’s signature jump throw amid a reel of acrobatic plays. The 2007 Rockies embarked on an unprecedented late-season surge to win the National League pennant, and while Boston prevailed in the subsequent World Series, Colorado looked set for long-term success. Rockies general manager Dan O’Dowd believed he could build around Tulowitzki as the Yankees built around Jeter, and Troy signed a six-year, $31 million contract extension before the 2008 season to embolden that plan.

Following a relative down year in 2008, Tulowitzki rebounded to earn MVP votes in 2009 – a .297 batting average complementing 32 home runs, 92 RBI and a .377 OBP. Successive All-Star Game appearances and Gold Glove nods affirmed Tulowitzki’s glowing reputation, and by 2010, he typically sat side-by-side with Jeter when pundits ranked the top shortstops in baseball. The age gap became increasingly apparent, though, and forward-thinking teams coveted Tulowitzki at 25 more than Jeter at 36. The Yankees ranked among that cohort, quite incredibly, though public criticism of Jeter was tantamount to pinstriped sacrilege, and internal disquiet over the team’s shortstop succession plan was supressed in deference to The Captain.

To wit, the second half of Jeter’s career spawned a dichotomy of opinion. Ardent evangelists saw Jeter as an omnipotent force – one of the all-time greats with an unmatched will to win. Meanwhile, vocal sceptics became preoccupied with replacing Jeter in the Bronx, often citing poor defensive metrics as rationale. Compared offensively to Rodriguez, Garciaparra and Rentería during his rise, Jeter was compared defensively to Tulowitzki, José Reyes and Andrelton Simmons during his decline. Sabermetricians ridiculed Jeter, slandering his elite intangibles at the altar of raw mathematics. Embracing advanced analytics, Cashman heard the hypotheses, and perhaps even agreed with the clichéd conclusions, but his hands were tied by Yankee mystique. Cashman may have wanted to replace Jeter, but he could not. Derek meant too much to the only franchise he ever loved.

Those tensions came to a head during the 2010-11 offseason, as ugly contract negotiations broached the legitimate prospect of Jeter playing elsewhere – a notion that last occurred 18 years earlier, when Derek entered the MLB draft. As detailed in The Big 50: New York Yankees by Peter Botte, Jeter’s agent, Casey Close, branded ‘insulting’ the Yankees’ opening offer of three years and $45 million. In repost, Cashman told Close to shop around and try to find a better deal. Duly engaged, Jeter’s camp asked Cashman to name an active player he would prefer at shortstop. “Do you want me to answer that?,” said Cashman, before uttering one name: Troy Tulowitzki.

In fairness, between 2007 and 2010, Jeter and Tulowitzki performed similarly:

Jeter-Tulowitzki comparison, 2007-2010 inclusive – per Fangraphs













World Series rings




























Yes, Tulowitzki was clearly a better defensive shortstop than Jeter, but the perceived offensive superiority of Tulowitzki was negligible, especially when factoring in Coors Field, the hitters’ haven at altitude where Troy played his home games. Tulowitzki had more power than Jeter and drove in more runs, but Jeter was a bat-to-ball savant with a penchant for getting on base. Moreover, Tulowitzki typically hit third or fourth for Colorado, while Jeter hit leadoff or second for New York. They were fundamentally different players, but between 2007 and 2010, it was a toss-up who produced more value for their respective teams. Given Jeter’s durability, leadership and winning instincts, the Yankees were right to stick by him, but Cashman’s admiration for Tulowitzki was understandable. Jeter signified the past, whereas Tulowitzki embodied the future.

Fittingly, Colorado signed Tulowitzki to another extension in November 2010 – this time for seven years and $134 million. Shortly thereafter, Jeter and the Yankees settled on a three-year, $51 million pact. Derek desired more than the $19.1 million average annual value (AAV) afforded Troy, but Cashman stopped hard at $17 million AAV. It was a subtle loss for Jeter, in a career of extraordinary wins, but he knew the power of pinstripes. By staying a Yankee for life, Jeter remained the darling of New York, eminently present in baseball’s definitive bubble. Tulowitzki knew that, too, and his own comparative isolation in Denver became a source of mounting frustration.

Troy Tulowitzki as heir to Derek Jeter

While it may be unfair to compare Jeter and Tulowitzki between 2011 and 2014, given the resounding age gap, a glance at the numbers reveals a clear disparity through those contract extensions:

Jeter-Tulowitzki comparison, 2011-2014 inclusive – per Fangraphs













World Series rings




























Jeter topped 3,000 career hits in 2011 and enjoyed a renaissance year in 2012, garnering MVP consideration with a .316 average , 216 hits and a .362 OBP. An ankle injury limited Jeter to 17 games in 2013, though, and while rehabbing, he announced the 2014 season would be his last. The Yankees gave Jeter a one-year, $12 million contract, and an epic farewell tour unfurled across MLB. 

On several occasions in 2014, Tulowitzki waxed lyrical about Jeter as The Captain prepared to retire. In addition, when Tulowitzki participated in the 2014 Home Run Derby, he chose Jeter’s Turn 2 Foundation as his nominated charity. Tulowitzki was beaten in the first round by Todd Frazer, but his six home runs raised $25,000 for Jeter’s charity. Derek thanked Troy for the kind gesture, and the pair shared some neat moments during the All-Star Game festivities in Minnesota.

Jeter took a photo with Tulowitzki’s son, Taz, for instance, then Derek embraced Troy at second base after hitting a double during the Midsummer Classic itself. This was a symbolic passing of the torch from one generation to the next, as Tulowitzki jostled for position in the race to succeed his idol. Jeter would leave multiple vacancies – as the face of baseball and as the Yankees’ shortstop – and Tulowitzki wanted to be considered for both roles. Tulo was next in line, and few could deny his destiny.

That time Troy Tulowitzki attended a Yankees game (while injured) to watch Derek Jeter

The quest to replace Jeter was largely cryptic, skirting baseball’s notorious tampering rules, but Tulowitzki fuelled wild speculation with a divisive stunt – classy to some, overzealous to others – on 27 July 2014. While rehabbing a left hip flexor injury, Tulowitzki met William Meyers, a sports hernia specialist, in Philadelphia, before driving to the Bronx for one last glimpse of Jeter in action. Attending a Yankees-Blue Jays game at the Stadium, Tulowitzki caught the attention of fans, reporters and the YES Network, which cut to the star at various points during its broadcast.  

After the game, Tulowitzki entertained the prospect of replacing Jeter – uncharted territory for two active players. “No doubt, I think everybody knows that,” Tulowitzki told the New York Post regarding the allure of succeeding Jeter. “Everybody wants that perfect story, whoever it may be. Whether it’s me or somebody else who took over for Derek, no doubt, it makes for a great story. But right now, it’s just talk until it gets closer to happening in the offseason.”

Some analysts did not appreciate Tulowitzki’s overt come-and-get-me plea, including ESPN columnist Ian O’Connor, who collaborated with Jeter on a biography and was one of few journalists trusted by The Captain. “This was another shortstop paying his respects – but getting the lay of the land at the same time,” wrote O’Connor. “This was a big-time athlete causing an unnecessary, big-time stir. This was Troy Tulowitzki, Derek Jeter fan, ripping a page out of the Alex Rodriguez playbook.”

Such a brazen move had to sting Rockies management, whose relationship with Tulowitzki deteriorated amid a steep organisational decline. Management became frustrated as Tulowitzki missed more time through injury, while the shortstop felt slighted by failed attempts to build a winning ballclub around him. A trade interested both parties, and divorce seemed inevitable. Meanwhile, tensions were exacerbated days before Tulowitzki’s Yankee Stadium pilgrimage when the Rockies misspelled his name on 15,000 giveaway shirseys. A franchise figurehead, Tulowitzki was understandably pissed, and his Bronx rendezvous sent a resounding message: the end was nigh – for Derek in New York, and for Troy in Colorado. Maybe fate would tie those threads together, adding another evocative ripple to Yankee iconography.

How the Yankees replaced Derek Jeter

Following one last walk-off single in his final game at Yankee Stadium, Jeter rode into the sunset – a first-ballot Hall of Famer who received 99.74% of the Cooperstown vote five years after hanging up his cleats. The Yankees shopped for a worthy successor, balancing fan gluttony with a rare chance to improve their infield defence. For Cashman, replacing Derek Jeter, the living legend, was a daunting task, but replacing Derek Jeter, the 40-year-old diminished shortstop, was far easier. Several candidates emerged as potential Jeter replacements, including Hanley Ramírez and Elvis Andrus, but most narratives focused on Tulowitzki, whose dream to succeed Jeter entered a critical phase.

In truth, though, the Yankees never seriously pursued a trade for Tulowitzki during the 2014-15 offseason. According to reports by Mark Feinsand of the New York Daily News, Cashman made initial enquiries with his Colorado counterpart, Jeff Bridich, but genuine momentum was not forthcoming. The Yankees were reticent to take on another large contract, and they also ignored Ramírez for similar reasons.

When deals for Andrus or Rollins never materialised, Cashman ultimately worked a three-team trade to land underrated Diamondbacks shortstop Didi Gregorius, a defensive whiz with an improving bat. Many scratched their heads at the move, including Tulowitzki, who receded further into obscurity with a perplexing Rockies core. So long awaited, his shot at replacing Jeter fizzled out – mirage more than miracle, reverie more than reality. An era drew to a close, as did Tulo’s Yankee dream. Rationality beat romance as daydreams went unfulfilled.

Where did it all go wrong? The sad demise of Troy Tulowitzki

In fairness, Gregorius was a productive, likeable Yankee for five years, hitting .269 with a stealth power stroke and dependable glove. Perhaps more importantly, Didi was durable, playing every day with little sign of wear and tear. By contrast, Tulowitzki was consistently derailed by injuries, to a point where staying on the field became a monumental challenge. Cashman probably made the right move dealing for Gregorius, though the symmetry of Tulowitzki replacing Jeter always seemed special.

Even during his prime, Tulowitzki dealt with nagging niggles, especially in 2012, but from 2013 on, lengthy absences zapped his once-amazing potential. Between 2013 and 2018, Tulowitzki missed 45% of his team’s scheduled regular season games. Whenever he did play, he was still very good, hitting .286 with a .356 OBP and a 119 OPS+ in that span. He just never played enough, and Tulowitzki became synonymous with injury-prone disappointment.

All told, Troy endured 12 different stints on the injured list during his career, with ailments ranging from knee problems, palm cuts, groin strains and hip tears to rib fractures, quad strains, hamstring tweaks and ankle sprains. Tulowitzki was made of glass, quite frankly, and Colorado finally traded him – to Toronto, of all places – at the 2015 trade deadline. The soap opera released a new episode.

Tulowitzki helped Toronto back to the postseason for the first time in 22 years, but his Canadian adventure was ultimately underwhelming. In 2016, Tulowitzki topped 130 games played for just the fourth time in his career, yet a .254 average and .318 OBP spoke to diminished skills. Various injuries limited Tulowitzki to just 66 games in 2017, and he missed the entire 2018 season due to heel surgery.

Toronto grew impatient with Tulowitzki and released him in December 2018 – despite owing the shortstop $38 million. It looked like the end for Tulowitzki, then 34 with a broken body that felt much older. Pathos drenched a once-glistening career, and requiems were written to a generational talent. The sad demise of Troy Tulowitzki was complete, bound to be retold for eons in the murky hue of mawkish disappointment. Except one last chapter gave the story a fuzzy ending – even if outright glory remained a stretch.

Troy Tulowitzki with the Yankees

Taking one last shot, Tulowitzki arranged an offseason workout attended by 11 big league teams. Some showed interest in signing Tulowitzki, perhaps to a minor league deal with an invitation to spring training, but one franchise stood out: the New York Yankees, who needed a stopgap shortstop while Gregorius recovered from Tommy John Surgery. Cashman offered a one-year major league contract with no-trade protection, and on 4 January 2019, Troy Tulowitzki finally became a Yankee. Sure, New York took a low-risk flyer on the shortstop, paying him just $555,000, but the symbolism was sweet. The ultimate Future Yankee finally earned his pinstripes.

“The Yankees and Derek always had a special place in my heart,” Tulowitzki told the YES Network in an introductory interview. “So to get a chance to play where my idol played meant something special to me. The franchise is about winning, and that’s what I have tried to do my entire career.”

Tulowitzki made an immediate impact with the Yankees, homering off Blue Jays ace Marcus Stroman in his first spring training at-bat. Tulowitzki pumped his fist rounding the bases, and rival fans pilloried him for such an emotional outburst in a March exhibition. Those critiques lacked sentiment, though. Troy Tulowitzki waited decades for that moment – to hit a home run as the Yankees’ shortstop – and the calendar could not dampen his joy. Besides, Yankees manager Aaron Boone praised Tulowitzki’s intensity, saying Troy set a professional tone for a ballclub determined to win. It was the Jeter doctrine in redux, and Yankees fans approved.

Alas, Tulowitzki only played five regular season games for the Yankees – mustering two hits in 13 plate appearances – before the injury bug returned with a vengeance. One of those hits was a home run into the short porch at Yankee Stadium, however, as Tulowitzki ticked another item off his bucket list. “Tulo-HIT-zki!,” yelped radio announcer John Sterling in one of his bespoke home run calls. “The man of Troy homers to right.” Derek did that a lot, too.

All told, Tulowitzki appeared in four errorless games defensively for the Yankees before succumbing to a left calf strain on 4 April. Tulowitzki reinjured the calf in a minor league rehab game, then took some time at home in Henderson, Nevada, to contemplate his future. Sadly, on 25 July 2019, Tulowitzki announced his immediate retirement from the Yankees and baseball. “I want to thank the Yankees organisation and Brian Cashman for giving me the opportunity to wear the Yankees’ uniform and live out another childhood dream,” said Tulowitzki in a statement. “I wish my health had allowed for a different ending to that chapter.”

Tulowitzki wanted to spend more time with Taz, then five years old. To that end, Troy later accepted a flexible role as a volunteer assistant coach for the University of Texas baseball team. He has maintained a relatively low profile post-retirement, and has become something of a forgotten figure in the baseball milieu. That was once an unthinkable notion, as Tulowitzki surged through his peak, but fate can be a cruel mistress, and few can resist its reign. 

The legacy of Troy Tulowitzki, Yankees’ forgotten legend 

“Sure, we had seen big shortstops before,” wrote Dan Mullen for ESPN in a definitive Tulowitzki tribute. “Cal Ripken Jr. was a big shortstop. Alex Rodriguez was a big shortstop. So was Derek Jeter. But we had never seen a big shortstop like this. At his best, Tulowitzki was Mike Trout at shortstop. He was Jeter with defensive metrics. He was, quite simply, the best shortstop in the game, with a chance to be one of the best players of his generation.”

Unfortunately, that version of Troy Tulowitzki is an afterthought these days. When talking or reading or thinking about Tulo, we tend to do so in the context of his unfulfilled potential – of what might have been if his body held up. But that narrative obfuscates another sad tale regarding Troy Tulowitzki: the unrealised dream, once so seemingly inevitable, of him as a Yankees icon. Instead of being the next Derek Jeter, he wound up with the same Yankee lifetime batting average as Jordy Mercer – .182. And that, ultimately, is how he will be remembered: a reclamation project that never panned out.

Nevertheless, Troy Tulowitzki lived his dream. Your dream. My dream. Our dream. The dream. Regardless of negative perceptions, it must have been cool for Tulowitzki to stand between second and third at Yankee Stadium wearing pinstripes in a major league game. Yes, he did it only four times, but that is four times more than you or I. Tulowitzki did in real life what I can barely do on MLB: The Show, and that should be celebrated, not lambasted, because the guy never gave up on his vision.

We should not be so snarky and judgmental when assessing the legacy of former players. We should respect how immensely difficult it is to merely reach the major leagues, let alone to stay there for 13 years while your body betrays you. Just think of Tulo’s journey. All those rehabs. All those lonely nights on the injured list. All that pain. To keep going, keep believing and keep persevering required guts and bravery beyond mortal kin. Have some appreciation for that. Celebrate what Tulowitzki did achieve in pinstripes, rather than lamenting what he did not.

Troy Tulowitzki did replace Derek Jeter as Yankees shortstop, in a roundabout way, and far be it for me – or anybody else – to nit-pick at that stirring achievement. Troy’s #12 will never hang in Monument Park, and Tulowitzki will never be considered an immortal Yankee name, but I appreciate his efforts in the Bronx, and those memories – while few – can never be taken away. So thank you, Troy, for a quirky vignette in Yankees history. There is only one Derek Jeter, but you have a pretty compelling story of your own.


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