Almost A Met: Roy Oswalt
Duaner Sanchez's ill-fated taxi ride in 2006 may have played a part here.
I’ll be honest, I was going to write about a different player this week.
But a follower on Bluesky (shoutout JPKMets!) asked me about a specific moment in 2006. What could have happened if RP Duaner Sanchez didn’t get into an ill-fated taxi ride?
Turns out: Maybe the Mets land SP Roy Oswalt.
As I did some more digging, I found out that the Mets and Oswalt had been linked to each other a few times. Scroll down to learn more about that.
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Anyway, let’s go back to 2006 and see what could have been.
Let’s get into it.
Andrew
The Mets 2006 rotation almost included Roy Oswalt
The 2006 Mets were a revelation for fans. The 2005 team teased us with potential, but the 2006 team was a juggernaut that steamrolled its way through the National League. It felt inevitable that they were destined for the World Series.
We all know what happened next.
If there was one weakness on the 2006 team, it was their starting pitching—specifically during the playoffs. SP Pedro Martinez and SP Orlando Hernandez were injured, leaving the team forced to use unproven starters like SP John Maine and SP Oliver Perez in large spots.
But what if they added one of the game's best pitchers to that rotation? Could the 2006 season be one we all look back on as a championship season instead of one that ended in heartbreak?
Maybe. Because the Mets were reportedly close to acquiring SP Roy Oswalt at the 2006 trade deadline.
How close was Roy Oswalt to being traded to the Mets?
It’s not hard to figure out what the Mets liked in Oswalt. In his first six seasons for the Houston Astros, Oswalt had an average of 5.6 WAR, and accumulated a 3.05 ERA. He struck out over 1,000 batters over 188 games, and was widely considered an ace.
He was potentially available because the Astros were very mid in 2006 and Oswalt was set to be a free agent after the 2007 season. The team ultimately finished with an 82-80 record, despite splashy names like SP Andy Pettitte and SP Roger Clemens pitching for them (not to mention Astros mainstays like 1B Lance Berkman, 2B Craig Biggio, and 3B Morgan Ensberg.)
Meanwhile, the Mets were looking to bolster their team. Around the 2006 trade deadline the Mets were 63-41, and clearly looking to make a deep run in the playoffs.
Adding someone like Oswalt to a rotation that included Tom Glavine, Steve Trachsel, Hernandez and Martinez would have been a major upgrade.
Mets GM Omar Minaya was reportedly deep in talks with the Baltimore Orioles and Houston Astros about a three-team deal that would have ultimately landed Oswalt with the Amazin’s.
Here’s how MLB.com put it in an interview with Assistant General Manager John Ricco in 2016: “On the eve of the Trade Deadline, Ricco and then-general manager Omar Minaya went to sleep hopeful they could land a front-line starter such as Houston's Roy Oswalt.”
According to the New York Post, the deal would have sent top prospect OF Lastings Milledge to Baltimore after they acquired Oswalt from Houston for SS Miguel Tejada.
In fact, there was a point during the trade discussions that the Mets “believed” they were going to get the ace, according to the Post.
Months later, Post reporter Mark Hale shed more light on the discussions at the time. The three-team structure was necessary because the Mets “didn’t have a hitter to deal,” a requirement that the Astros wanted as part of any deal for their ace.
Despite that, the Mets were “prepared to do anything in their power” to land Oswalt, and according to the Post, and some names floated in potential deal were SP Mike Pelfrey, SP/RP Aaron Heilman, and SP Brian Bannister, in addition to Milledge.
Adam Fisher, the former Mets front office executive, told Moose & Maggie during a 2020 WFAN interview that the trade was close and would have made a “huge difference.”
“We had a legitimate trade on the table for Roy Oswalt during the 2006 trading deadline that fell through, and that obviously would have made a huge difference,” he said.
As we all know, the Mets never landed Oswalt. Instead, the team’s whole strategy needed to shift quickly.
RP Duaner Sanchez, who had been lights-out in the bullpen for the Mets in 2006, was hurt in a taxi accident in Florida. The accident ended up dislocating his pitching shoulder.
“Not only did we lose him, but it kind of changed our whole view of what we needed to do,” Ricco told MLB.com.
Shortly before the trading deadline, the Mets—desperate for relief help—ended up shipping OF Xavier Nady to the Pittsburgh Pirates for RP Roberto Hernandez and the aforementioned Perez.
Mets and Oswalt 2.0 (and 3.0)
A few years later, the Mets were once again connected to Oswalt.
Ahead of the 2010 trading deadline, the Mets were extremely middle-of-the-road, and there was some thought of them trying to acquire Oswalt once again. The ace had $33 million left on his contract, and the Astros were looking to ship him to a contender.
While there was some speculation, a lot of reports suggested the match was unlikely.
New York Post reporter Mike Puma cautioned Mets fans to not “hold their breath” on an Oswalt acquisition, while MLBTradeRumors noted that his contract would be a factor in any trade.
Oswalt was sent to the Philadelphia Phillies, where he posted a 1.74 ERA over 13 games. He would pitch for them for the 2011 season as well.
But even after that there was even more talk about Oswalt and the Mets. In 2013, ESPN reported that the Mets had some interest in Oswalt even after they made the bargain-bin signing of SP Shaun Marcum. However, his agent later said he wasn’t aware of any interest.
Overall, it appears that the Mets had interest in bringing in Oswalt numerous times (over different years and under very different circumstances) but it was never meant to be.
There’s no doubt that the addition of Oswalt to the 2006 team could have made a huge difference, and who knows what would have happened with him at the top of the rotation during that playoff run.
We like to dream here in this newsletter.
❓ Would you have made the trade?
Let’s get in the GM chair. Would you have traded OF Lastings Milledge and another prospect for SP Roy Oswalt as part of a three team trade?
Next newsletter we’ll share the results of the poll! So stay tuned.
Last newsletter’s answers: 78% of Almost A Met readers said they would not have made a blockbuster deal to acquire Kris Bryant at the 2001 trade deadline, while 22% said that they would have.
⚾ Mets news you need to know
Zack Scott, the former Mets GM and Boston Red Sox front office executive, brought up the Manny Ramirez-to-the-Mets talks on X after the bonkers Rafael Devers trade. I guess we were just a few weeks early with our Manny newsletter. (@ZackScottSports/X)
Mets left-hander Brooks Raley began his rehab assignment this week. The Mets hope he can help the big league team in July. (@AnthonyDiComo/X)
The Mets All Star Game caps were released. As you can imagine, they aren’t good. (@lovethemetsbot.bsky.social)
👀 Next time on “Almost A Met”
Next newsletter will be something different! Our first “Almost A Met” manager. We’ll be looking at how Lou Piniella was a “top candidate” for the Mets manager role in the early 2000s.
Got a suggestion for who you want us to feature in an upcoming newsletter? Send us an email at: almostametnewsletter@gmail.com