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Top 10 Yankees what ifs

BRONX, N.Y. — It’s around this time of year that you count your blessings and what you’re thankful for. While the New York Yankees have come up short since 2009, my stocking are stuffed with five World Series titles in my lifetime. That said, across the years doesn’t everyone have that present or two extra that didn’t quite make the cut on your wish list?

With that, I present to you my top 10 realistic hypotheticals in my life as a Yankee fan.


I was tempted to go with Justin Verlander in 2017 but these Yankees were defending champions and needed to maximize all that was remaining of the “Core Four.” One could practically taste the repeat champagne in July 2010. New York had a tentative deal with the Seattle Mariners for Cliff Lee, where they’d send Jesus Montero, David Adams, and Zach McAllister to the Pacific Northwest. Yet, the M’s balked at Adams’ physical and asked for either Eduardo Nunez or Ivan Nova as a replacement. Alas, the Yankees would not include either one. Plus, they’d eventually trade Montero for Michael Pineda before the 2012 season.

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While Lee got batted around by the San Francisco Giants in the World Series that year, if you’d paired him up with CC Sabathia and Andy Pettitte, you’re probably ensuring at least a trip back to the Fall Classic if nothing else.


It’s those little meticulous details that help you win championships. Along with Marino Rivera, Mike Stanton and Ramiro Mendoza, Jeff Nelson was a vital part of some championship Yankee bullpens. For a couple of million bucks more, chump change for pinstripe brass, the team could’ve kept that intact. Not to mention that they’d trade back for him a mere two seasons later in 2003. Nelson would post a 2.76 ERA with the 2001 Seattle Mariners and earn an All-Star nod.

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Imagine having him instead of trading for Jay “at least I can say I got to pitch in a World Series” Witasick or Mark “Jim Leyritz destroyed my career” Wohlers? Imagine keeping the “formula” intact? Imagine if instead of Rivera being taxed with two innings, Nelson pitches the eighth inning in Game 7 of the 2001 World Series, and a fresh Rivera slams the door in the ninth inning for the four-peat?


The Yankees sign Johnny Damon not after 2005 but after 2001. With the Oakland Athletics, Damon hit .409 against the Yankees in the ALDS. He seamlessly replaces Chuck Knoblauch in left and atop the order. The Yankees then don’t sign injury-prone Rondell White. Damon retains the fire and grit lost by the retirement of Paul O’Neill as well. Plus, he never goes to Boston.

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Had the Yankees won in 2001, “The Boss” probably doesn’t go off the deep end with a roster shakeup. Hence, I’m sticking with the consistency and stability of Tino Martinez at first base. Did Jason Giambi have the higher production ceiling? Sure. Was he a good dude? Yes. However, you also don’t have to deal with the PED baggage, price tag, defensive liabilities, or injury issues.

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I hedged on Carlos Beltran and or Vladimir Guerrero. As much as I loved Gary Sheffield’s fire and booming swing, I would’ve signed Guerrero instead prior to the 2004 campaign. While Guerrero is also better than Beltran, Beltran fits better with my hypothetical. Granted one could go with a hypothetical outfield/DH setup including Bernie Williams, Damon, Guerrero, and Beltran, they’re only handing out so many monster deals and I’m assuming they still sign Hideki Matsui.

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Beltran appeared to be the logical heir-apparent to Williams, even dating back to his Kansas City Royals days. A centerfielder who switch-hit had speed and power and was coming off a monster postseason in 2004. The Yankees instead fronted in claiming that Williams was still the centerfielder, even though they’d brought in Kenny Lofton the year before and would spot start Tony Womack there in 2005 and eventually sign Damon for 2006.

Under my scenario, you’d have some combination of Beltran, Matsui, Damon, and Williams rotating between the outfield and DH. Plus, if Beltran is still going strong, the team probably never signs Jacoby Ellsbury, Beltran never goes back to Houston, wins a crown with the Yankees in 2017, and eventually becomes the manager instead of Aaron Boone.


The old Branch Rickey adage is, “trade a player a year too early than a year too late.” Matsui earned 2009 World Series MVP honors and was a career .312 hitter in the postseason. While it’s difficult to quantify “clutch” and Matsui was on his last legs/creaky knees, he was built for the October stage in New York. Matsui essentially replicated his regular-season stats from 2009, after signing with the Los Angeles Angels in 2010.

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What’s most damning is his replacement. The Yankees signed injury-prone Nick Johnson. When Johnson broke down, they dealt Mark Melancon and Jimmy Parades to the Houston Astros for Lance Berkman. While Berkman would tear it up for the St. Louis Cardinals in 2011, he looked essentially beat in the Bronx.


He wasn’t the first Yankee star to be shown the door this way and he won’t be the last. Yet, Williams deserved better than being offered a minor-league contract prior to the 2007 season. His roster spot was given to Josh Phelps, who lasted all of 36 games in pinstripes. Williams certainly had enough left in the tank where he would’ve been more than competent at DH and as a fourth outfielder.

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Plus, it would’ve been cool to have seen Williams make it to the last year of the old Yankee Stadium in 2008 and maybe to the new Yankee Stadium in 2009. Ala Paul O’Neill, the crowd chants “Bernie Baseball,” as Williams rides off into the sunset as a World Series champion for the fifth time.


This move harkened back to the 80’s Yankees when they allowed Reggie Jackson to walk. Pettitte was a pillar of the 90s dynasty foundation and a hoss for nearly a decade at that point. While there were legitimate concerns about his elbow, he deserved the benefit of the doubt. A homegrown, fan-favorite, lefty pitcher, champion.

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I still remember driving back from classes and listening on WFAN when the news came down. To say I was shocked and upset would be an understatement.

Yes, Pettitte needed surgery in 2004 but maybe if the Yankees had brought him back and he still went down, they could’ve coaxed Roger Clemens out of retirement. Hopefully, as a result, the 2004 ALCS collapse never happens. Plus, perhaps you don’t have the parade of malcontents like Kevin Brown, Javier Vazquez, Randy Johnson, Jaret Wright, and Carl Pavano. That the team eventually brought back Pettitte in 2007 further proved how ill-advised this move was. Pettitte didn’t miss a beat and would eventually help the club win the 2009 World Series.


There’s a lot of different factors here but this one would’ve been fun. In 2012, Derek Jeter led the junior circuit with 216 hits. It felt like he was poised for a second wind and would follow his boyhood Yankee idol Dave Winfield and play well into his early 40s. Maybe he’d even make a run at Pete Rose.

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Alas, Jeter would break his ankle in the 2012 ALCS and was never fully back to form. Jeter played a mere 17 games in 2013 and was about a replacement-level player at age 40 in 2014.

Perhaps he still would’ve left after bitter contract talks, not wanting to eventually shift to another position or DH or playing for some mediocre Yankee teams.

Yet, it would’ve been fun to have seen him stay healthy in 2012, the Yankees possibly beat the Detroit Tigers in the ALCS, maybe win the World Series and stay competitive from there on out. If Jeter averages the 192 hits he did from 2009 to 2012 for the ensuing five seasons, he totals 4,264 hits, breaking Pete Rose’s record of 4,256. On top of that, he helps the Baby Bombers win it all in 2017 and goes out a champion for the sixth time. The Yankees and Jeter make oodles of money off marketing and he eventually buys a share of the team.

Even if we’re conservative and he averages 160 hits per season in that timespan and ends up with 4,104, that ranks third all-time and he’d be one of three players ever with more than 4,000 hits. Still not too shabby.


Prior to the strike, the 1994 squad sported a ledger of 70-43, tops in the junior circuit. It was a mix of players, an easy group to like and rally around, and a team on the rise. It also would’ve been nice to have seen some of the guys there from the bad times win a ring, most notably Don Mattingly. The Yankees and Montreal Expos World Series would’ve been a blast. Gene “Stick” Michael and Buck Showalter both get a ring in their respective positions.

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I ran out of spots to change the outcome of 1995, I’ll assume the Torre dynasty years played out as they did because sometimes you get a good surprise in your stocking.