15 free agent (and trade) near-misses that would've changed Yankees history

In the New York Yankees' long and venerable franchise history, they've earned 27 World Series titles, a pile of hardware the rest of the league is still looking way up at, even after a down few decades.

Therefore, MLB's other 29 teams can't summon an ounce of pity for the game-changing acquisitions and free agent additions the Yankees almost made over the years, but instead narrowly missed on.

These near-misses stick out most during the 2017-present "empty" era without a title. Yankees whiffed on a free agent in 1993? Alright, well ... we know it all worked out for them. Yankees miss on a number of acquisitions that could've pushed them over the edge while the Baby Bombers were still on their rookie deals? Yeah. Those still sting.

Considering the stakes and the details, these near-misses stand out in recent Yankees history. Some of these deals you'll be glad the Yanks never completed, but others could've changed the franchise's trajectory for the better (and could've prevented the Astros from doing big things).

HONORABLE MENTION: When Zack Greinke went to the Astros at the buzzer at the 2019 trade deadline, which robbed the Yankees of their best chance of upgrading their roster and saw the Bombers lose out to a rival ... yet again. That said, from what we know of Greinke, he was never coming here, and wouldn't have prospered.

15 near-misses in free agency and trade market that could've changed Yankees history

Marcus Stroman Trade, 2019

The only thing Marcus Stroman being traded to the Yankees in 2019 absolutely could've prevented was a whole mess of Twitter blocking. If a Stroman-Yankees trade had been completed, there would be plenty more Bronx Bomber fans freely @ing Stro Show to this day and engaging in pleasant conversation.

Alas ... it was not to be.

Stroman was heavily rumored to be a Yankee in 2019, entering the deadline with a 2.96 ERA in Toronto, with just 99 Ks in 124.2 innings pitched. Instead, Brian Cashman found the price too high, famously stating that he "didn't think [Stroman] would be a difference-maker," and that he envisioned him in the Yankees' bullpen come October.

Stroman did not take this well. Rumor has it he threw a tantrum in the locker room when he learned he was "coming home" to the Mets and not the Yankees, and he has continued to attack the Bombers on Twitter to this day as pitching-weak.

Stroman went 4-2 with a 3.77 ERA that August and September for the Mets, allowing more hits (65) than innings pitched (59.2).

Starling Marte/Robbie Ray Trades, 2020 MLB Trade Deadline

At the time, this seemed like a fairly obvious outfield upgrade for a Yankees team that entered 2020 as a prohibitive favorite, only for the year to go completely off the rails with a pandemic no one could've forseen the day Gerrit Cole signed on the dotted line.

Conversely, Robbie Ray felt like a poor Cashman decision in the making; the high-strikeout, high-walk, high-struggle left-hander seemed likely to be dealt for more than his worth. Projections had the Yankees ending up with both players.

Marte went to the playoff-bound (!!!) Marlins and actually struggled down the stretch (86 OPS+), but in the tiniest 28-game sample size that could've easily reversed itself in October, when the Yankees relied heavily on Brett Gardner instead. Ray went 1-1 with a 4.79 ERA, but could've changed the path of the 2021 season, winning the Cy Young in Toronto over Gerrit Cole.

The Yankees notably stood pat at this deadline, a plan that unraveled when Deivi Garcia/JA Happ combined to start a playoff game while their offense couldn't touch the Rays.

Matt Olson Trade (Rumors), 2021-22

Were the Yankees ever really close to trading for left-handed slugging first baseman Matt Olson? Back in the winter of 2021-22, this seemed like a natural fit for a lefty-light lineup that was prepared to say goodbye to Anthony Rizzo, who fit in nicely in the second half of '21, but wasn't as young or threatening as Olson (or quite as legendary as Freddie Freeman, who was also available).

When the CBA was approved, the Yankees were deemed "not close" to Oakland's asking price, and fans who'd spent the past few months creating fervor on Twitter had to look at themselves in the mirror and decide whether they'd just been writing elaborate fan fiction.

Ultimately, Olson went to the Braves, then immediately signed a long-term deal including a donation to the elusive Braves Foundation. He slugged 34 homers and posted a 122 OPS+.

Rizzo, brought back by the Bombers, whomped 32 homers with a superior 131 OPS+, and didn't require another long-term deal to make the trade a win/isn't weighing on the Yankees' books for longer than two years. Add in the assets surrendered for Olson and the leadership Rizzo provides, and New York might be in a more dangerous position if they'd followed the Twitter leaders here.

Pablo Lopez-Gleyber Torres Trade, 2022

Of all the "close calls," this one might've been the closest.

America may never know whether Cashman actually believed this swap was done done and prematurely pulled the trigger on the Jordan Montgomery/Harrison Bader trade, believing he wasn't sacrificing any pitching at all. It's a logical story, though. All we know is that MLB insiders have confirmed this trade was quite close to being finalized, and reading about it threw Gleyber Torres off for the entire month of August, his worst as a Yankee.

Instead of adding Lopez and Frankie Montas at the deadline, the Yankees acquired only the injured Montas, who was good for eight ill-advised starts. Add the Andrew Benintendi wrist snap and Scott Effross' pre-postseason Tommy John, and you have one of the darkest timelines imaginable.

Lopez posted a 4.61 ERA last August himself, and probably wouldn't have been well-liked by those eternally-patient Yankee fans anyway.

Gerrit Cole Trade, 2018

Another recent instance where the Yankees were viewed as favorites from the second a player hit the market, only to hem and haw over whether or not to include Underwhelming Talent A or Failed Prospect B before a rival stepped in and finished the deal.

The Yanks were "in the lead" for a Gerrit Cole trade with the Pirates after the 2017 season for quite a while, but couldn't figure out a package led by either Clint Frazier or Miguel Andújar. Who knows whether the Pirates wanted one, both, or neither, but eventually the Astros got the job done with a Joe Musgrove/Colin Moran-fronted package.

Musgrove didn't figure it all out until leaving the Pirates, while Cole had one of the best pitching seasons in recent history for the 2019 Astros (20-5, 2.50 ERA, 326 Ks in 212.1 innings). He also turned the tide on the 2019 Yankees with his gutsy Game 3 ALCS start in the afternoon sun at Yankee Stadium, earning a mega-deal in New York a few months later.

Pitching with the Yankees had always been his dream. Imagine how incredible it would've been to secure those two additional prime years and toss Monster Cole in Game 1 of the 2018 ALDS at Fenway instead of JA Happ?

Manny Machado Trade, 2018

At the 2018 MLB trade deadline, Orioles star Manny Machado firmly believed he was switching teams in-division and heading to the New York Yankees as Aaron Boone attempted to chase down the 108-win Red Sox from behind.

'I thought I was going there [to New York],' Machado told reporters Monday in Los Angeles, according to NJ.com. 'I guess the trade didn’t go through and I went to the Dodgers. I don’t really know the full story, but I thought I was going there [to the Yankees].Me and New York go back a long time. I played there (for Baltimore) and fans always showed me love. It’s a special place. … I thought I was going there and then it didn’t happen.'

It would've been great. It could've ignited the rivalry after Machado had already become persona non grata in Boston by spiking Dustin Pedroia. It wouldn't have cost that much; the Dodgers eventually dumped Dean Kremer and a number of underwhelming prospects on the Os, who knew they were losing Machado that offseason regardless.

Unfortunately, the Yankees couldn't close the deal.

The Machado rumors didn't end that summer; some believed New York was still the presumptive favorite to sign the star third baseman in free agency following the conclusion of the 2018 World Series.

They ... were not; Cashman, Steinbrenner and Co. didn't open up the wallet that offseason for either Machado or Bryce Harper, preferring to save money for Gerrit Cole the next offseason. Because that's certainly a choice the all-powerful Yankees had to make. One or the other, not both. Never both. Always one. Good stuff.

Vladimir Guerrero, 2003

The 2003-04 offseason set the Yankees up for ALCS failure in Boston almost as clearly as can be. It's basically a one-for-one comparison. Make bad move, end up short-handed. Choose wrong option, end with regret. Add Kevin Brown's contract, watch him shatter his own hand for fun.

Essentially, the only thing the Yankees did that offseason that worked was signing Gary Sheffield ... but even that move came with a tinge of regret, as they could've had Vladimir Guerrero. They could've had him for longer. He could've won the 2004 AL MVP in New York instead of Anaheim, potentially going head-to-head with Manny Ramirez in a memorable (and victorious!) postseason war.

Guerrero was reportedly Cashman's preference. George Steinbrenner? He'd long displayed a "fascination" with Sheffield, who was famously ex-Mets legend Dwight Gooden's nephew.

Sheff worked. Guerrero would've been a better idea. And who knows? Maybe Vlad Jr. isn't going on Yankee-hating diatribes if his father had won a ring or two in the Bronx. Maybe he chooses the Yankees instead of the Jays as an amateur. The ripple effects of this one are spooky. Even spookier than letting Andy Pettitte walk in free agency for some reason and relying on Javy Vázquez, Esteban Loaiza, Jon Lieber and Brown with the season on the line.

Cliff Lee, 2010 (twice)

The Yankees somehow managed to botch the Cliff Lee situation twice, coming perilously close to the Cliff's Edge without closing the deal. Sure, New York did capture the 2009 World Series, but they plainly needed Lee to push them over the top into potential dynastic territory in the waning years of the Core Four, unable to trust AJ Burnett and infuse their rotation with talent beyond CC Sabathia/Andy Pettitte.

The Phillies traded Lee to Seattle after the '09 World Series, but despite getting an excellent first half from their new ace, the water-treading Mariners made him available at the deadline once more. The Yankees' deal was ~RUMORED TO BE~ done, featuring Jesus Montero as its headliner, alongside righty Zach McAllister and infielder David Adams. Unfortunately, a physical flagged a foot issue in Adams, and the Yankees were unwilling to replace him with Eduardo Nuñez.

Their loss! Lee instead went to the Texas Rangers for a Justin Smoak-centered package and buzzsawed the Yanks in the 2010 playoffs, much the same way he had in '09. Texas advanced to the World Series in large part because of Lee's 16 innings of two-run ball against the Rays and his eight-inning shutout with 13 Ks against the Yanks, defeating Pettitte 8-0.

At least the Yankees were still the favorites to sign the rental after the season! Right? ...Right?

Eh, no. Lee went back to the Phillies, and spurned the Yankees amid an unpleasant storyline that fans had spit on his wife during the Rangers ALCS, which might've been the most pivotal postseason series loss of the era, non-Derek Jeter's ankle division.

Justin Verlander, 2017

Hey, remember when the Yankees had an opportunity to trade for an ace midseason, only to see him go to a burgeoning contender in Texas instead and ultimately upend their pursuit of a title? Just thinking about that again for no reason.

The Justin Verlander non-trade in '17 likely swung two AL titles, minimum, and the world where the Yankees end up with both Cole and Verlander in 2018 while the Astros ride Lance McCullers 'til he breaks is ... not worth stressing over, but SUPER stressful to think about. Could've happened. Really could've.

The Yankees (and Dodgers) reportedly turned down the Tigers' overtures in both July and August of 2017 because they had no interest in paying Verlander's $25 million salary and adding it to the luxury tax pot. It should be noted, too, that Verlander wasn't an absolute home run sure thing; he posted a 10-8 record and 3.82 ERA with Detroit that season at the age of 34.

But ... postseason hoss, dominant ace, difference-maker. It wasn't just hindsight.

We all know what happened next. Verlander went 5-0 with a 1.06 ERA in five regular-season starts, bulldozed the Yankees and Dodgers in the playoffs, and finished 2-1 in the next two Cy Young ballots in '18 and '19. And the Yanks could've had him for a little luxury tax payment (and it's not like the 2018 or 2019 Yankees spent meaningfully!) and Daz Cameron.

Bernie Williams Nearly Bolts for Red Sox, 1998-99

The Yankees of the '90s would've been more than just a nice little historical footnote even if Bernie Williams had left after the 1998 season. They would've just set an all-time wins mark, after all. The narratives would've been juicy. "Can this dynasty keep itself together without its calming glue in Williams?"

The potential intrigue lost doesn't balance out how harrowing it is to think of Williams on the Red Sox in 1999, 2000 and 2001, though. And that's exactly what would've happened if the Yankees' front office hadn't bent to his will.

Williams entered the 1998-99 offseason reportedly wanting to remain a Yankee, but the Sox offered him seven years and $91.5 million, while New York offered just five years and $60 million. That's good business. If Boston had been able to pull off this coup, neuter the Yankees and flex their financial muscle, they could've reversed the curse five years earlier and muzzled New York in the midst of a budding dynasty. It would've been brutal.

Thankfully, the Yankees upped their offer to $89.7 million for seven years, though it didn't come before another twist of fate. Joe Torre wanted to swing for the fences and grab the moody Albert Belle, who was all set to accept that five-year, $60 million offer ... before he backed out and chose Baltimore instead. If not for Belle being a fickle weirdo, the Yankees would've added his worst years to their payroll while watching Williams pepper the Monster -- and, oh yeah, the Yanks and Sox locked horns in the ALCS that fall.

Greg Maddux, 1992

The Yankees' botched signing of Greg Maddux during the fabled 1992-93 free agency cycle only doesn't rank higher because ... well, because the Yankees owned the "Team of the '90s" Braves regardless, even after coming away from this offseason with Jimmy Key instead.

That said, the '90s Yankees almost had an absurdly different roster, as Maddux, then a Cubs star, truly believed he'd be signing with the team. Due to extenuating circumstances -- namely, a Yankees front office member suffering a heart attack -- Maddux claims he never received a formal offer, and was forced to move on to Atlanta.

Of course ... that's the version of the story he tells now. Back in 2014, Maddux claimed Yankees GM Gene Michael actually offered more money than Atlanta, but that the bespectacled ace preferred to stay in the National League.

Whatever the case, the professor would've been a pretty intimidating co-pilot with David Cone. Ironically, having Maddux in place for the sliced-off 1994 season would've felt a little like getting stuck with Gerrit Cole for the 60-gamer in 2020. The Yankees would've done all they could and still fallen short thanks to an act of God -- or Bud Selig.

Yankees-Braves Mega-Deal for Jason Heyward and Co., 2014-15

The Baby Bombers Era might not have brought the World Series titles Yankee fans envisioned back in mid-2017, or after a crushing ALCS loss that season that still felt like the "start of something."

But ... at least it happened, right? At least Aaron Judge is the Yankees Captain and will be here for life instead of being an Atlanta Braves outfielder. At least Luis Severino has a contract year to work with in the Bronx instead of the Battery. At least the Yankees didn't have to absorb the decline years of Jason Heyward and BJ Upton.

That's what almost happened back in the 2014-15 offseason, when a Yankees-Braves monster trade fell apart just before the finish line.

The proposed deal had Judge, Severino, Gary Sánchez, along with left-handers Ian Clarkin and Manny Bañuelos, heading to Atlanta in exchange for Chris Johnson, BJ Upton, Jason Heyward, Andrelton Simmons and reliever David Carpenter. A rare "Win-Extremely Lose" trade!

Hilariously enough, the Yankees eventually swapped Bañuelos for Carpenter (with Chasen Shreve tucked in there, too). That was probably for the best. Not a trade that will be remembered in the annals of history, but at least New York didn't nab Chris Johnson and mortgage their entire future to do it.

Mariano Rivera-David Wells Trade/Felix Fermin Trade, 1995-96

The only unanimous Hall of Famer in baseball history was almost traded multiple times prior to the start of the Yankees dynasty. Who knows how many titles the '90s team wins without Mariano Rivera at the back end, erasing multiple innings at a time in every crucial playoff game?

It is NOT EASY TO WIN THE WORLD SERIES OR CLOSE THE WORLD SERIES. Rivera, himself, fumbled away the 1997 ALDS, 2001 World Series and 2004 ALCS, and he's the greatest closer to ever live. Imagine someone with a less lethal pitch trying to do it from '96-'12? Imagine (gasp) the Yankees mixing and matching in the role?

While Rivera rested a shoulder injury during the summer of 1995, Yankees GM Gene Michael nearly swapped him for David Wells of the Detroit Tigers; Boomer later found himself in New York anyway under much better circumstances. Again the next spring, when Derek Jeter was ticketed for the starting shortstop job but no one was quite sure he was ready, George Steinbrenner and Co. nearly dealt Rivera again, this time to the Mariners for also-ran Felix Fermin.

Steinbrenner was reportedly "pushing hard" to swap either Rivera or Bob Wickman for Fermin, while Brian Cashman and Joe Torre spent hours talking him down. The trade dissolved, and Fermin played 11 more big-league games, all for the 1996 Cubs. He hit .125.

Barry Bonds, 1992

Yup. The big one. Imagine the scope of the steroid scandal if Bonds hadn't followed his godfather Willie Mays and father Bobby to San Francisco and joined the Giants in the 1992-93 offseason, but instead had wound up shaking hands with the Yankees? Pure chaos. He probably would've ended up banned for life (or eventually welcomed onto ESPN's Sunday Night Baseball broadcast).

According to Bonds (ironically as related on ESPN's KayRod Cast this past fall), the Yankees offered him a four-year, $36 million offer, but put a quick time limit on it. As Bonds grabbed lunch and tried to process the fact that the Yankees front office was hassling him, his agent called and told him the Giants had just outbid New York anyway. Bonds preferred to go home, and the rest was history.

But who knows? If the Yankees have a higher initial offer or don't push Bonds to shake their hands, maybe he chooses them before the Giants ever call? Maybe Maddux agrees, too (or they make a formal offer)? Maybe the '90s Yankees have the greatest left-handed slugger of all time taking aim at the short porch from 1993-1996, while Bernie Williams cowers in Boston?

Either way, history was changed that offseason, and it's amazing the Yankees didn't knock their championship train off the tracks right then and there.

READ MORE: 15 Worst Free Agent Signings in Yankees History