5 missed trade deadline opportunities that will haunt Yankees' Brian Cashman forever

Flags Fly Forever, what a wonderful phrase. Flags fly forever, it ain't no passing craze. It means no worries and a championship parade. As Yankees fans, it's our motto. We want to win, and that means going all in at times.

Few prospects pan out to the point where you would regret trading them in exchange for a World Series ring. For the Yankees, in the last 25 years, I can count them on two fingers: Aaron Judge and Robinson Cano. And with the Yankees' financial resources, there's no excuse not to move a highly touted prospect on a team-friendly deal for the final piece to a championship puzzle. You can replace them in your roster construction with a free agent after the season.

Unfortunately, Brian Cashman's track record doesn't reflect this same philosophy. For him, the motto is, "Making the playoffs is good enough." How else can you explain a laundry list of missed trade deadline opportunities, during seasons where the Yankees were a stone's throw from baseball immortality and the Commissioner's trophy? 

5 Brian Cashman trade deadline blunders that may have prevented a Yankees World Series

Tanner Scott (2024)

Game 1 of the 2024 World Series. Tenth inning. Runners on first and second. Aaron Boone goes to the mound and signals for the left-hander, Tanner Scott, to face Shohei Ohtani. Ohtani, who's 1-for-9 lifetime against Scott, pops out to left field. Two batters later, after intentionally walking Mookie Betts, Scott faces Freddie Freeman with two outs and the bases loaded - except, instead of hitting a walk-off grand slam, Freeman strikes out and the Yankees win the opener.

Somewhere in the multiverse, that happened. But in this universe, we all know Tanner Scott wasn't on the team, so Boone chose to go with Nestor Cortes (instead of Tim Hill), and Cortes blew the game. 

The most frustrating part of the equation is that, going into the trade deadline, every diehard Yankees fan from Brooklyn to Westchester knew they needed bullpen help, especially left-handed help. Scott, a lefty, was the top relief arm on the market, and the San Diego Padres got him for four prospects, headlined by Robby Snelling. The Yankees could have topped that package or taken back a bad contract from the Marlins, such as Avisail Garcia, to finalize the deal. 

Justin Verlander (2017)

Flashback to the summer of 2017, and the Baby Bombers are surging. What was supposed to be a rebuilding year is now Aaron Judge's coming-out party. The rookie sensation is on his way to a 52-home run season, and the Yankees have a legitimate chance to win the AL pennant.

They acquired Sonny Gray at the trade deadline, and the only thing standing in their way was the Houston Astros, and, unbeknownst to the Yankees, a trash can. Houston had been the best team in the league all summer, but were starting to fade in August (69-37 entering the month, 11-16 during August), and that's when Jeff Luhnow took Brian Cashman to school. Luhnow pulled off a last-minute deal to acquire Justin Verlander from the Detroit Tigers, in essentially a salary dump, sending Franklin Perez, Daz Cameron, and Jake Rodgers to Detroit at the now-nonexistent August waiver trade deadline.

Verlander had five starts in the regular season with Houston in 2017 and allowed four runs in 34 innings. Then he won the ALCS MVP against the Yanks by tossing 16 innings of one-run ball, including seven shutout innings in a must-win Game 6. The following year, he finished second in Cy Young voting, and the year after that, he won the Cy Young. Houston beat the Yankees again in the 2019 ALCS, and the Astros went 1-1 in Verlander's starts, but he pitched well outside of one bad inning in the Bronx.

It's not as if the Astros made a godfather offer (an offer you can't refuse) to pry Verlander from the Tigers; this was a waiver trade deadline deal, where the Tigers just wanted to get out from under the contract, and Cashman stood by and let his main competition scoop the prize. 

Cliff Lee (2010)

It was the best of times, it was the worst of times (for the rest of the American League); the Yankees were defending champions and entering July with the best record in baseball. They knocked off the Phillies in the 2009 Fall Classic (in six games), and Cliff Lee won twice for Philadelphia.

During the offseason, the Phillies traded Lee (because they thought they couldn't afford him) to the Mariners, who weren't a good team (they lost 101 games in 2010). And the Mariners put Lee on the trading block during the summer. He wasn't the reason they were bad; he was in the midst of another great season (7.3 fWAR in 2010, led all pitchers).

The Yankees were interested and the prohibitive favorites to acquire him. They had a deal on the 'one-yard line', but then it all fell apart. Cashman pulled a 'Cashman' and snatched defeat from the hands of victory. 

The Yanks were going to send star prospect Jesus Montero, David Adams, and Zach McAllister to the Mariners in exchange for Lee, except ... the M's found a problem with David Adams' ankle, and instead of pivoting and including Adam Warren, Ivan Nova, or Eduardo Nuñez, Cashman played hardball, and the deal collapsed. The Texas Rangers swooped in and acquired Lee, who dominated the Yanks in the ALCS, tossing eight scoreless innings, striking out 13, and allowing a mere three baserunners. Texas won the pennant and then lost to San Francisco in the World Series. 

The failure of the Lee trade is just another example of Brian Cashman thinking he's the smartest guy in the room and botching a deal that any fan in Billy's or Stan's could close.

Randy Johnson (2004)

Some Yankee fans might be too young to remember Hal's dad, George Steinbrenner. Whereas Hal has a hands-off approach to roster management, George was a superfan who wanted to be involved in every decision. In the summer of 2004, he had his eyes set on a lanky left-hander in Arizona, one who had beaten the Yankees in the World Series a couple of years earlier, and who baseball writers would later induct into the Hall of Fame. Cashman pushed back and didn't want to pay the Diamondbacks' price, and Steinbrenner capitulated, setting the stage for the biggest collapse in baseball history. 

Despite winning the pennant in 2003, Cashman re-tooled the Yankees' starting rotation in the offseason. The result was tragic. The 2004 Yanks didn't have a qualified starter with an ERA under 4.00. Cashman replaced Andy Pettitte, Roger Clemens, and David Wells with Kevin Brown, Javier Vázquez, and Jon Lieber, but the offense was fantastic. 

They won the first three games of the ALCS against the Red Sox. Then. Orlando 'El Duque' Hernández started Game 4 and Mike Mussina got Game 5, but the Yanks lost both of those in extra innings. Instead of Randy Johnson, they had Lieber and Brown on tap to pitch Games 6 and 7. Curt Schilling outdueled Lieber in the 'Bloody Sock' game, and Brown didn't make it out of the second inning in Game 7. The Yankees lost the series, and the Red Sox beat the Cardinals to break the Curse of the Bambino. 

Later that offseason, the Boss got his guy, and the Yankees traded Vázquez, Dioner Navarro, and Brad Halsey to the Diamondbacks for Johnson. If that trade happened in July, the Yanks would have won the pennant, Vazquez had a 9.95 ERA in the ALCS, and Johnson finished second in Cy Young voting. 

Curt Schilling (2000)

The suggestion of Curt Schilling in pinstripes is enough to send chills down any Yankees fan's spine. However, before the bad blood (no pun intended) between Schilling and the Yankees, he practically took out a full-page ad in the Daily Post that said, 'Trade for me.' 

The Yankees didn't need him to complete the three-peat and beat the Mets in the Subway Series in 2000. However, in the 2001 World Series, Schilling had a 1.69 ERA in 21 innings and won co-MVP honors with Randy Johnson; the Yankees lost in seven games. 

The midseason trade that sent Schilling from Philadelphia to Arizona netted the Phillies Travis Lee, Nelson Figueroa, Vicente Padilla, and Omar Daal, which the Yankees could have easily topped. The butterfly effect from not getting Schilling includes the Yankees' inability to prevent him from waltzing to the Red Sox in 2003 when the D-Backs pivoted. This one missed trade could have spared Yankees fans the trauma of Luis Gonzalez's walk-off AND the 'Bloody Sock' game. For that reason, it might be the worst missed opportunity in franchise history.