Joba Chamberlain reveals Yankees almost traded him for a Hall of Famer (twice!)

The New York Yankees won the 2009 World Series with fan favorite/top prospect Joba Chamberlain floating between the rotation and bullpen. As a vaunted hurler with upside, Chamberlain was — naturally — in the trade deadline crosshairs quite a bit with the "win now" Yankees, and it's somewhat surprising he survived both the '09 "go for it" deadline and the next few seasons of trying to scale the mountain once again.

Chamberlain recently joined the Yanks Go Yard Podcast for his second appearance to recap the 2024 trade deadline and detail his own midsummer experiences. Unsurprisingly, the right-hander found himself nearly traded several times during his Yankees career — and one deal got so close (twice) that he was taunted by Toronto Blue Jays staffers when he traveled north of the border.

Ultimately, Chamberlain didn't leave the Yankees until signing with the Detroit Tigers in 2013-14's offseason, reuniting with good friend Austin Jackson from his previous organization. But, when asked about sighs of trade deadline relief (addition by subtraction, etc.), the flamethrower mentioned not one, but two near-misses where he (and Phil Hughes) were almost packaged in exchange for Roy Halladay.

Yankees Podcast: Joba Chamberlain joins Yanks Go Yard, shares trade deadline and 2009 World Series stories

"It was back-to-back years," Chamberlain recalled. "It was weird, because Len Frejlich is the visiting clubhouse manager in Toronto. And we became good friends. Toronto is special to me, because that's where I made my first ever appearance, so it holds a special place in my heart. And literally at the deadline, every time we'd go back and play Toronto, Len had been like, 'Oop. Heard you're about to get traded again for Doc'. God rest his soul, as well."

Chamberlain recalled that he took the razzing in stride, as he'd heard the same thing. "At that point, it's not like you could make a decision. I'm young, and it's like ... sure! I'd never been to Canada until two years ago, so, you know," he mused.

The Yankees opted to stick with Chamberlain, who never made another MLB start again following that 2009 campaign, but remained a valuable cog on the roster. Halladay was dealt to the Philadelphia Phillies prior to the 2010 season, winning the Cy Young that year, and throwing both a regular season perfect game and a playoff no-hitter against the Cincinnati Reds.

The Yankees appear to have pursued Halladay following the '09 season, and public rumors certainly swirled at the previous summer's deadline, too. Luckily, flags fly forever, and who knows what ripple in time would've shifted if the 2009 team had moved two key setup men in Chamberlain and Hughes for Halladay within the division? As it stands, Chamberlain pitched three innings in the World Series, whiffing four and allowing a solo homer (in a game where A-Rod later delivered some heroics). We'll take that, and forget about the alternate reality.