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The Tuesday Discussion – My All-Time Favorite Shortstop

This week we asked our writers

Who is your favorite Yankees shortstop of all-time?

Here are their responses:


Tamar Chalker – I’m a 90s kid, so it’s hard not to pick Jeter. I got to watch his entire career unfold as I became a bigger and bigger baseball fan. Sitting in the bleachers at Fenway for his very last game is one of my favorite all-time baseball memories.


Paul Semendinger – When I posed the question, I had a feeling that this one might be unanimous, that the answer from all would be Derek Jeter. (We will have to see as the answers come in.) For me, I cannot think of another person who it could be. It was a joy to watch Derek Jeter over the amazing twenty years of his career. There were so many great moments, so so so many. There were also the many championships. It was a great time to be a Yankees fan. Derek Jeter was a huge part of that.

For me, the answer is simple.

It’s Jeter.

The shortstop, number two, Derek Jeter.

Honorable mention goes, of course, to Didi Gregorius. (The blog is called Start Spreading the News, right?)

Finally, if you missed my Bucky Dent story last summer, you might enjoy reading it now.


Lincoln Mitchell – About a year or so ago I was invited back to my high school in San Francisco to give a book talk to some students. The event was open to alumni as well. After the event, one of the alumni approached me. I recognized him right away. We had played on the baseball team in 1982. I was a freshman bench warmer and he was a senior and our best player. We had a nice conversation and he asked me if I was still a big Yankees fan. I said yes. He then said “I remember you really liked Roy Smalley.” Roy Smalley was acquired by the Yankees in the very beginning of the 1982 for reliever Ron Davis. I was intrigued by Smalley because he was a power hitting shortstop at a time when that was still very rare. Robin Yount had not really emerged a as a slugger and Cal Ripken Jr. was a top prospect in the Orioles system at the time. In 1979, Smalley had hit .271 with 24 home runs, but slumped slightly in 1980 and 1981. I hoped he could repeat those 1979 numbers and help the Yankees. Smalley hit very well in 1982 and 1983 with the Yankees, posting an OPS+ of 113 with 45 home runs 1,300 plate appearances, but injuries forced him off of shortstop and made him less valuable. The Yankees sent him to the White Sox midway through the 1984 season. Derek Jeter is without doubt the greatest shortstop in Yankees history, but for some reason, Roy Smalley remains my favorite.


Ed Botti – We all know who the best shortstop in team history, and possibly MLB history is. He would be the guy that conned Mr. Cashman into taking on a $218 MM contract for an often injured DH.

“Holy Cow, what a Huckleberry”, my selection would have said!

Although I am too young to have seen him play, my favorite shortstop is an ex MVP who won 9 pennants and 7 world series as a player in 13 seasons. He was elected to the Hall of Fame in 1994. Oh yeah, he also served in the US Navy for three years during WWII.

That would be the “Scooter”, Phil Rizzuto.

His 1,588 career hits and 149 stolen bases ranks him second, only to Jeter among Yankee shortstops.

If you were around to listen to him call games back in the day on WPIX, you will know why.

I had the honor of meeting him once, and he was one of the nicest men I ever met!

Honorable Mentions: Bucky Dent and Tony Kubek


Chris O’Connor – Derek Jeter is the obvious pick here, so I’ll break away and go with Didi Gregorius. I am fortunate to be young enough to really have only seen two long term shortstops in Derek Jeter and Didi Gregorius. Though I only caught Jeter towards the end of his career, I loved watching Didi slowly grow out of Jeter’s shadow and develop his bat enough to become a solid 20 homer, 80 RBI player with the Yankees. There is something to be said for watching a player slowly break out into an above average player with your team. Whether it was his infectious energy and passion for the game or his clutch postseason moments (his 3-run homer in the first inning of the 2017 wild card game might be my favorite Yankees moment I have seen live), Didi played a huge role in the rebirth of the Yankees circa 2017. I would have loved the team to re-sign him after 2019, but he brought so many great memories for me.


Tom Russo – Let’s be honest, It has to be Derek Jeter. I modeled my style of hitting growing up after Jeter’s opposite field stroke because he was THE Yankees growing up in the early 2000s. Add in his spectacular jump throws from the hole that defined an era of defenders at the shortstop position and you’ve got everything you could ever need in a superstar.


Owen Hetherington – Growing up, Derek Jeter was the only shortstop anyone my age knew. He was the most consistent player that the Yankees had up until he retired in 2014. Although Jeter is going to be the most common answer to this question, I think I might have to steer in another direction, for personal reasons.

The date was December 10, 2014, only three short months after the Captain walked away from baseball. It was a cold, snowy night in upstate New York when Jeter made an appearance as a guest speaker for Hamilton College’s Great Names series. I was in attendance at the event with two of my buddies and one of their fathers. After the event on our way home, my friend’s father realized that Jeter was flying out of the former Griffis Air Force Base where he worked. After a quick phone call, we found ourselves in the hanger where Jeter’s jet awaited. Besides us, I think there were only 4-5 other people in the hanger. After about 20 minutes of waiting, two blacked out Cadillac Escalades pulled up and out stepped the Captain and his sister. He didn’t even take a look at us, who were less than 10 feet away from his car when they pulled up and jumped on his jet. That was my only encounter with Jeter in my life and will likely be the last. I don’t know what I was expecting, possibly at least a wave or a hello. I’m not going to say that Derek Jeter not waving to me ruined my perspective on him, heck, I still have a poster of him hanging up in my room at college. But, because of my encounter, or lack thereof with Derek on that snowy night, I’m rolling with Didi as my favorite shortstop.

Didi played the game with intensity and passion in his stint with the Yankees. Looking back, I don’t think there could have been a better player to replace the Captain. He was fun to watch and always played the game with a smile on his face. It always seemed like he came up to the plate in big moments and he never let the moment get too big for him. He had a sweet stroke at the dish, and in all honesty, played better defensively at short than Jeter did for the majority of his career. I miss seeing Didi in the lineup and wish he was still a part of this team.


Mike Whiteman – Derek Jeter of course is a Yankee legend, synonymous with the Yankee “brand”. Watching him throughout his career was just awesome. Someday, when I’m old(er) I’ll tell young folks about him (“Now Derek Jeter, he was a real ballplayer’).

Yet, I have to give Didi Gregorius some love here. I remember thinking “Why did the Yankees get this guy?” when he was acquired, and then “Why are they letting him go?” when he left. He started as a glove only shortstop and made himself into a fine all-around player, developing while standing in as the successor to an icon. I think the team missed his left handed bat and leadership in 2020.

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Start Spreading the News is the place for some of the very best analysis and insight focusing primarily on the New York Yankees.

(Please note that we are not affiliated with the Yankees and that the news, perspectives, and ideas are entirely our own.)


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