curt schilling yankees red sox
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Former starting pitcher Curt Schilling was a thorn in the Yankees’ side on multiple occasions throughout his MLB career. He helped the Diamondbacks beat New York in the 2001 World Series while also achieving October glory with the Red Sox in 2004 and 2007.

But what if at least one of those last two things didn’t happen? The Bombers badly wanted to sign Schilling after the 2003 season. In fact, they wanted him so bad that they were willing to let him “fill in the check” to whatever deal they agreed to.

The right-hander talked about the situation he was in during that offseason on The Bret Boone Podcast. Here’s a bit of what he shared (which is around the nine-minute mark):

I thought I was going to be a Yankee – My wife wanted to go to New York and I heard Boston was 25 guys, 25 cabs, and all this other stuff.

I told Joe Garagiola, I said ‘Hey, listen, if Boston’s interested, I’d be open to listening.’ He walks literally from me across my backyard to Jerry Colangelo, comes back five minutes later, and says ‘Just so you know, Boston’s already made a trade for you on the condition maybe you waive your no-trade. They’ll be here Thursday morning and they have 72 hours to sign you.’”

One of the things I remember very vividly about the Boston thing is I had the Yankees on my phone in the interim saying ‘Hey listen, just don’t sign there. Let the window run out and when the window runs out we’ll be there Saturday morning and you can fill in the check. We don’t care.'”

I was like ‘This is kind of nice leverage to have’ but at the end of the day, the choice between Boston and New York came down to this: I can go be a Yankee and be a part of World Championship 27, 28, maybe 29, or I can go to Boston and do something no one alive has ever seen before.

They said ‘We can’t pay you more than Pedro,’ – But you’re bringing me there to win a World Series so if I help bring the goods I want to get paid for it so I negotiated those things into the deal and I ended up making every penny of that money. We won two and it was everything you thought it could be.”

This was quite the turn of events. Isn’t it interesting that Alex Rodriguez nearly joined the Red Sox before landing with the Yankees and the opposite happened with Schilling? I don’t know — maybe it’s just interesting to me.

It’s possible New York appeared desperate to also keep Schilling away from Boston. His first season with the Red Sox resulted in a 21-6 record to go along with a 3.26 ERA, 1.06 WHIP, and 203 strikeouts in 226.2 innings pitched during the regular season.

Across four starts that October (22.2 innings), the hurler went 3-1 with a 3.57 ERA as the Red Sox broke their 86-year World Series drought.

You can reach Matt Musico at You can follow him on Twitter: @mmusico8.

Matt Musico is an editor for ESNY. He’s been writing about baseball and the Mets for the past decade. His work has been featured on numberFire, MetsMerized Online, Bleacher Report, and Yahoo! Sports.