The hot stove is running cold right now, so this week we’re running a series of guest posts from Sam Tydings, Steven’s brother. Sam used Out of the Park Baseball to simulate some past “what if” Yankees scenarios. We’ve already looked at the Greg Maddux non-signing, the Albert Belle non-signing, the Vlad Guerrero non-signing, and the Cliff Lee non-trade. Now it’s time to look forward with Bryce Harper and Manny Machado. You can follow Sam on Twitter at @simmonsclass.

We’ve spent the last week looking at pivotal moments from the Yankees recent past, so for the final installment of this series, let’s take a look at the team’s immediate future. With Spring Training right around the corner, it seems like the Yankees roster is set, aside from adding maybe a swingman or a few non-roster invites.

Though we have heard all offseason not to count them out until the ink is on the page, it seems highly unlikely that Manny Machado or Bryce Harper will be joining the team at Steinbrenner Field in a few weeks. Better writers than I have spent the entire offseason making a case for the Yankees to sign one, the other, or both, so to wrap things up things up this week, let’s take a look at the most tantalizing option and give Harper and Machado a (fake) home in the Bronx.

One of the reasons offered as to why the Yankees should pass on signing either big name free agent is that it would inhibit the team’s ability to lock up their homegrown talent down the road. If you are one of the people citing that as a reason to avoid both stars, the results of this sim are for you.

I signed Machado to a 7-year, $186 million contract (a steal) and Harper to a 9-year, $326 million deal (probably more in line with what he ends up getting). The signings paid immediate dividends, as the Yankees won 105 games to cruise to the AL East title and eventually the pennant. Harper hit 46 homers en route to the MVP, while Machado hit 32 and brought home the Gold Glove at 3B. The team brought home title number 28 in 2020 and everything seemed good in fake Yankeeland.

Unfortunately, the big money handed out to Machado and Harper reared its ugly head as the team chose to let Masahiro Tanaka and James Paxton walk, leading to rapidly diminishing returns from a once strong rotation. The team did not make it back to the World Series for the duration of either of their contracts. Both players finished their careers with over 550 home runs, were elected to the Hall of Fame in their first years of eligibility (Harper 98%, Machado 94.2%), and both even went in as Yankees.

Here is fake Harper’s career (click for larger view):

And here is fake Machado’s career (click for larger):

However, the idea of signing both of these players to long term contracts at their young ages is to ensure a dynasty comparable to the late 90’s teams, or if you want to be incredibly optimistic, the dynasties from the 40’s. The Yankees as currently constructed are probably good enough to win one of the next few World Series without adding either Harper or Machado, so winning just one in a decade with both of them staying healthy would be an unparalleled disappointment.

There was an assumption from the moment that he debuted on the cover of Sports Illustrated that Bryce Harper would don the pinstripes at his first opportunity, and Machado has been linked to the team since at least last year’s winter meetings, if not earlier. There are probably Yankees fans out there who are already photoshopping Vlad Jr. into a Yankee hat and trying to figure out where he would hit in the 2025 lineup.

For a variety of reasons, these dreams rarely come to pass. The Sabathia coups are much less common than seeing Cliff Lee, Max Scherzer, and David Price end up on another team’s roster. On its face, the Yankees offseason so far has been a success. They’ve added a very good pitcher to their already strong rotation, added to the best bullpen in baseball, and increased their depth in the infield. Considering how much of the rest of the league seems to not have an interest in winning, it has been an extremely productive winter for Brian Cashman and company.

The Yankees can afford to add Harper and Machado to shore up two of the only relative weaknesses on their roster and they should, simply for the fact that it would keep two elite players from joining other teams. Do they need either one to be successful? I don’t think so. If Out of the Park Baseball is to be believed, even bringing both into the fold would not guarantee an instant dynasty.

But 26-year old talents rarely hit the open market in any year, much less two in the same winter, so why not take advantage of the cold stove? If any organization in the league is built to withstand the inevitable circus that would come with such a power move, it is the Yankees. Most baseball fans will lose their minds over the Yankees spending big and cornering the market again. But not only has every other team had plenty of time to lock in either player, I have a very large sim file which shows that even in a Yankees fan’s fantasy offseason scenario, it might work out in a way that will make the Yankee haters happiest of all when the final story is written.

The hot stove is running cold right now, so this week we’re running a series of guest posts from Sam Tydings, Steven’s brother. Sam used Out of the Park Baseball to simulate some past “what if” Yankees scenarios. We’ve already looked at the Greg Maddux non-signing, the Albert Belle non-signing, and the Vlad Guerrero non-signing. Now it’s time for the Cliff Lee non-trade. You can follow Sam on Twitter at @simmonsclass.

The morning of July 9th, 2010 was a crucial one in recent Yankees history. At the time, the defending champion Yankees had a 3-game lead in the AL East over the Rays and a 5-game lead over the Red Sox, and the team was in Seattle for their final series before the All-Star Break, scheduled to face M’s ace Cliff Lee that night. The Mariners were tied for the 2nd worst record in the American League, despite trading for Lee in the final year of his deal over the winter to pair with young ace Felix Hernandez in an attempt to make their first playoff run since 2001.

There had been light speculation about where Lee would be moved, but then all hell broke loose on the morning of the 9th. A deal sending top prospect Jesus Montero, along with infielder David Adams and pitcher Zach McAllister to Seattle for Lee was just about done. Until it wasn’t. Whether it was a legitimate concern or a ploy to get Texas to up their offer, the Mariners pulled out of the deal over Adams’ medicals, shipping Lee to the Rangers, who he would lead to the AL pennant before spurning the Yankees again in December to join the Phillies.

So as Yankees OOTP Week (or whatever you end up calling this) continues, let’s take a look at an alternate universe where Lee ends up in pinstripes for the stretch run in 2010. Thank you, Force Trade button:

The fake 2010 Yankees immediately take off with Lee helping to anchor the rotation. Instead of dueling with the Rays for the division title, the Yankees cruised to a 104-58 record, topping their 2009 mark. Meanwhile the Lee-less Rangers clung to the American League West at 82-80. The teams ended up meeting in the fake ALCS, but with Lee on the Yankees, the series is a rout. The Yankees ended up only dropping one playoff game en route to their 2nd straight championship. Lee went 12-1 with just a 1.84 ERA for the team after the trade, leading to his second Cy Young award.

Fun fact: the 2010 Yankees gave 19 second-half starts to Dustin Moseley, Sergio Mitre, and Ivan Nova.

Congrats, Cliff! We’re all very happy for you!

Perhaps wooed by the ring, Lee stayed in New York with a massive 5-year contract that featured an opt-out after just two years. Fake Lee would go on to lead the Yankees to another pennant before bouncing around the league, finishing just shy of 75% on his final Hall of Fame ballot. It is difficult to see a reality in which a Lee trade does not result in at least the Yankees’ second straight pennant if not another title. Lee was ultimately felled in that 2010 World Series by the likes of Freddy Sanchez, Cody Ross, and Edgar Renteria of course, so anything is possible.

The key component of the Lee trade heading to Seattle was Montero, who was a few months removed from being tied to a Yankees trade for Roy Halladay, and 18 months until he was ultimately flipped to the Pacific Northwest but for Michael Pineda instead of a bona fide ace. Had Lee come to New York and won a title regardless of signing an extension, the trade would have been immediately justified. If he had a similarly awful World Series as the one he pitched in Ranger blue and red and headed to Philadelphia anyway, we would still be ruing the lack of value received for Montero, even if he struggled as he did in Seattle.

Obviously with hindsight being what it is, the Yankees should have dealt Montero in a package for Halladay at the 2009 Winter Meetings if it was truly on the table, instead of refusing to send their top prospect in-division. The 2009-2012 contention window had many fond memories, but it was clear at the time and more so now almost a decade later that the team needed another frontline starter.

There are a myriad of reasons why the Lee trade could have been a disaster for the Yankees: the playoffs are random, he might have ended up hating New York and leaving without delivering a title, maybe Montero thrives with more seasoning in Seattle (ok, probably not that last one). Regardless, if the Yankees weren’t being nakedly used for leverage over the course of a year, they missed their shot to deal their best hitting prospect in a decade from a position of depth for an ace who could have added a couple of more flags to the new stadium’s facade.

The hot stove is running cold right now, so this week we’re running a series of guest posts from Sam Tydings, Steven’s brother. Sam used Out of the Park Baseball to simulate some past “what if” Yankees scenarios. Yesterday we looked at the Greg Maddux non-signing. Today it’s the Albert Belle non-signing. You can follow Sam on Twitter at @simmonsclass.

It is hot stove season, which means it is officially time to picture every top free agent in Yankee pinstripes and without facial hair, while assuming the team will retain anyone they want to keep around as they pursue championship number 28. Currently the team is looking to build its next dynasty and fly more flags, but the 20th anniversary of a moment that nearly broke up the last Yankees dynasty recently passed.

In November of 1998, the Yankees not only nearly failed to keep Bernie Williams, but would have (allegedly) allowed him to sign with the Boston Red Sox. Had Williams walked, the Yankees would have purportedly signed temperamental outfielder Albert Belle, who was coming off of a year where he hit .328/.399/.655, leading the league in OPS and hitting 49 homers. Belle opted out of the last 3 years and $30 million dollars of his deal with the White Sox, ultimately signing a 5 year, $65 million deal with the Orioles. But what this blog presupposes is…what if he didn’t?

Thanks to the majesty of Out of the Park Baseball, I simulated the world where Bernie teamed up with Nomar to lead the 1999 Red Sox while Albert Belle tried to keep the Yankees emerging dynasty going.

I feel like George’s expectations probably would have been higher than this Opening Day lineup!

The fake 1999 season was an extraordinarily compelling one. The Yankees and Red Sox battled all season long, with the Bombers ultimately compiling 102 wins to Boston’s 101, good enough for a division title and ultimately the same ALCS matchup and result that actually occurred, as the Yankees defeated the Red Sox in 5 games before beating the Astros in 5 to claim their 25th World Series.

Belle hit 25 homers but struggled in the playoffs, while Bernie slashed .329/.406/.520 with 22 homers for the Red Sox. Then things got weird. The Red Sox shipped out Bernie after one season to clear budget space for some free agent signings, and the Rockies and Orioles ended up being the dynasties of the mid 2000’s. Belle never topped 27 homers with the Yankees, retiring after only playing 13 games in 2003. He topped out at just over 60% of the fake Hall of Fame vote before falling short, while Bernie never got over 20%, but did pick up a few rings with the Rockies, to put a bow on a stellar career and one way the story could have gone.

Had Bernie actually walked, I highly doubt the Yankees would have gone into the 1999 season with Tony Tarasco starting in center field like our fake Yankees did. Certainly by 2000, the team would have acquired a longer-term solution in center by trade or free agency. By Opening Day 2000, Jim Edmonds would be traded from the Angels to the Cardinals for Adam Kennedy and it is easy to picture Edmonds tracking fly balls in death valley at the old stadium and making highlight reel catches, even helping to cover for Belle’s lack of defense in the corner.

But one more interesting option might have been on the table for a fascinating what-if of its own: noted Yankee killer Ken Griffey Jr, who famously rejected a trade to the Mets before accepting a trade to Cincinnati before the 2000 season. At the time, Griffey was not said to be willing to accept a trade to the Yankees either, but with Bernie entrenched in center, the Yankees’ need wasn’t as pressing. But it’s hard to see the Yankees not being willing to throw together an offer around enticing (at the time) names like Ricky Ledee, Randy Keisler, Drew Henson, maybe even Alfonso Soriano if it meant Griffey would be taking his talents to the Bronx.

The Yankees dynasty of this simulation died on the vine after the 1999 title, but with Belle and Edmonds or Belle and Griffey, it could have potentially surpassed the heights the team ended up reaching. Of course, it easily could have fallen far short. Ultimately, we should all be thankful Cashman/Boras/Bernie were able to work something out to keep the dynasty alive and leave Belle’s tenure in pinstripes as a hypothetical, even if they should have won a few more titles along the way.

The hot stove is running cold right now, so this week we’re going to run a series of guest posts from Sam Tydings, Steven’s brother. Sam used Out of the Park Baseball to simulate some past “what if” Yankees scenarios. We begin today with the Greg Maddux non-signing. You can follow Sam on Twitter at @simmonsclass.

The hottest Broadway shows. The biggest contract given to a pitcher in MLB history. Donald Trump. These were supposed to be the deciding factors behind Greg Maddux leaving the Cubs to join an upstart Yankees club looking to make a big free agent splash in the winter of 1992. Instead Maddux spurned the Yankees, who had not made a playoff appearance since 1981, in favor of joining a Braves team which had won back-to-back NL pennants but had yet to get over the hump and win the World Series.

The Yankees not only missed out on Maddux, but every free agent pitcher they targeted that winter, including David Cone, Doug Drabek, and Jose Guzman, along with Barry Bonds, who left Pittsburgh for San Francisco that winter despite the Yankees making some overtures. Perhaps this could be attributed to the fact that George Steinbrenner was still suspended by Major League Baseball due to the Howie Spira/Dave Winfield issue. Of course, Steinbrenner ceding day-to-day operations of the team, including roster control, to Gene Michael was a net positive in the end as it assuredly kept the Yankees from shipping off the entire Core Four (and Bernie!), even if it meant whiffing on the class of ’93.

Maddux left $6 million on the table, a big deal in pre-strike MLB money, in order to form one of the most formidable rotations in MLB history. The mid to late 1990’s turned out pretty well for both Maddux (three Cy Youngs and a World Series ring) and the Yankees (four titles, two over Maddux’s Braves), but let’s imagine a past where Maddux takes the Yankees’ monster offer and joins a future dynasty with Bernie Williams, Don Mattingly, and Paul O’Neill on the MLB roster and the Core Four waiting in the wings in the minors.

The 1993 Yankees were the sign of an extremely bright future in the Bronx, as the team tallied 88 wins, sparking a run of finishing above .500 that continues to this day. Of course, the team failed to win the AL East and were winning the division handily in 1994 when the strike ended play in August. Adding Maddux to the team changed everything in a hurry. Our fake OOTP ’93 Yanks led the league with 108 wins, led by Maddux’s 19-8 record and an incredible 190 ERA+ in a league-leading 291 innings. Unfortunately, the team was vanquished by Yankee killers Edgar Martinez and Ken Griffey, Jr. in the ALCS. Here are Maddux’s numbers:

Of course, the team’s run of dominance was only just beginning, as adding players like Andy Pettitte, Mariano Rivera, Derek Jeter, and Jorge Posada, all who were in the Yankees’ system by the time Maddux signed, turned the AL into a laugher. Starting with the 1995 season* the Yankees won seven straight pennants and nine out of ten, including the 1995-1997 and 2000 and 2003 World Series. Maddux was of course incredible, winning three Cy Youngs, two MVP’s, and a World Series MVP along the way, cementing his spot in Yankees lore and the MLB Hall of Fame. Yes, it is possible that the Yankees were one move away from having an even more dominant run than we experienced twenty years ago.

* A quick caveat on Out of the Park Baseball: It plays out the 1994 season as scheduled and a full 162-game schedule for 1995. So for this exercise we have to suspend our disbelief for a little and pretend that the richest team adding the best pitcher to a huge contract would have done away with the strike instead of exacerbating tensions.

As Maddux helped prove in Atlanta, the MLB playoffs are a random beast. Every dynastic team experienced a huge break or two along the way, on the field or off, and every would-be dynasty was denied some of those same breaks. The 1999 Braves had an 8th inning lead in two World Series games but all it is remembered for is a Yankees sweep to cap off a dominant century of play.

Maddux to the Yankees might have been enough to push the team past Toronto in ’93 but more importantly, it raises the ceiling on the championship window that already existed. Would Maddux at the peak of his powers in 1995 been enough to give the Yankees the AL East and avoid the Seattle team that would ultimately fell them? Would it have been enough to propel the Yankees past the rest of the American League in 1997?

With an ace missing from the Braves’ rotation, does another team fill the power void in the National League to play spoiler to the Yankees dynasty we all knew and loved, or would they have just been replacement victims in the background of our World Series VHS collection? The Yankees missed out on Maddux, but obviously did not miss out on the parades. It is the most stereotypical Yankee fan complaint in the world, but the 90’s dynasty somehow could have been even better, and everyone would have hated the Yankees just that much more.