What if the Orioles never made the Erik Bedard trade?

All across SB Nation this week, sites are posing the amazing, frustrating, and sometimes terrifying question: What if?

The last 20 years of Orioles baseball could be broken up into two eras: before the Erik Bedard trade, and after.

It would have been fair to refer to the O’s as a “bumbling” franchise from the late '90s through the first decade of the 2000s. They couldn’t get out of their own way, making poor decisions in free agency, struggling to develop their own players and cycling through managers and GM’s every season or two.

In the summer of 2007, Orioles owner Peter Angelos hired Andy MacPhail to serve as the club’s GM, replacing Mike Flanagan. During his first off-season in charge, MacPhail struck a deal that would, in part, bring winning back to Baltimore.

The Orioles sent Erik Bedard, their talented 29-year-old ace, to the Seattle Mariners in exchange for five players. The headliner was 22-year-old outfielder Adam Jones, one of Seattle’s top prospects, who was expected to start in right field for them in the upcoming campaign. Instead, he would man center field in Baltimore for the decade to follow.

In addition to Jones, the Orioles also added 19-year-old pitcher Chris Tillman, 23-year-old pitcher Kam Mickolio, 30-year-old southpaw George Sherrill and 21-year-old pitching prospect Tony Butler.

You already know what happens from there. Jones becomes, arguably, the best center fielder in team history. Tillman serves as a steadying influence in the Orioles rotation for years. Sherrill makes an all-star team before being flipped to the Dodgers for prospects (including pitcher Steve Johnson). Mickolio makes a few appearances with the O’s before being packaged and traded to the Diamondbacks for slugger Mark Reynolds. And Butler, unfortunately, flames out in Delmarva.

The deal laid a base on which the Orioles built a winner. It didn’t exist in a vacuum, of course. Vital trades for J.J. Hardy and Chris Davis followed. Not to mention the drafting of Manny Machado among others.

For the Mariners, they got the ace they were after, and Bedard performed well while in Seattle, posting a 123 ERA+ and 3.31 ERA, but he never threw more than 83 innings in a season for them. In 2008, Bedard’s season was cut short by arthroscopic shoulder surgery in July. In 2009, he missed the second half of the season with a torn labrum, which also cost him all of 2010. The deal was a disaster for the M’s, one of the worst in team history.

So, it begs the questions, for both teams:

What if the Orioles never made that Erik Bedard trade?

The Orioles finished the 2007 season with a 69-93 record. Sam Perlozzo had been fired as manager midway through the year, and Dave Trembley took the reins. Around the same time, MacPhail was put in control of the front office.

Bedard, despite being on one of the worst teams in the league, generated some Cy Young buzz that season. His 221 strikeouts over 182 innings (he led the league with a 10.9 K/9 rate), paired with a 3.16 ERA and 15 wins earned him a fifth-place finish for the award, tied with Roy Halladay, Johan Santana and Justin Verlander. His value had never been higher.

With two years remaining before he could hit free agency, and the Orioles still quite a ways from contending, the two sides had reached a pivotal decision. Trade Bedard and cash in on his value, hold onto him and see what happens, or pursue a long-term contract.

Based on some of the quotes that came out following the eventual trade, an extension wasn’t gonna happen.

[Bedard] said the Orioles never made a true effort to sign him to a long-term contract; MacPhail said Bedard never wanted to stay.

“I made an inquiry early with Erik’s representatives,” MacPhail said. “They were polite, but I certainly got the sense that their preference at the current time was to take it on a short-term basis.”

(h/t ESPN)

With MacPhail being the new GM, it seems equally unlikely that the Orioles would have sat on their hands either. Bedard wasn’t going to be with the club long-term, and they lacked the top-end prospects needed to build a contender. Something had to be done.

According to a prospect list from Minor League Ball made in January of 2008, these were the Orioles top five prospects prior to the trade:

1. Matt Wieters, C
2. Troy Patton, LHP
3. Radhames Liz, RHP
4. Bill Rowell, 3B
5. Nolan Reimold, Of

Wow. Just wow. Further down the list are some familiar names, like Jake Arrieta, Brandon Snyder, Scott Moore, Brad Bergesen and David Hernandez. So, it wasn’t completely bare, but you get the idea.

MacPhail knew that he needed to reinvigorate the organization with young talent, and a trade of Bedard was the best way to make it happen. In addition to the Mariners, the Orioles were said to be talking with the Mets, Dodgers, Reds and Indians about a potential deal involving their coveted lefty.

The Orioles weren’t messing around either. MLB Trade Rumors notes that the Orioles told the Reds that in order to get Bedard they would have to give up Homer Bailey, Joey Votto, Johnny Cueto and Edwin Encarnacion. The O’s were willing to include 36-year-old Melvin Mora as a makeweight. Talk about swinging for the fences.

Who knows how close that deal actually came to happening. My guess is not very. If it had, that would have been an even more monumental trade than what actually happened.

What’s more likely is that the Orioles were trying to publicly push the Mariners to include Tillman in the deal. The two sides seemed to have agreed on Jones as the centerpiece for a long time coming. The quarrels came over the secondary stuff, with the Mariners preferring to trade Brandon Morrow or Carlos Triunfel rather than Tillman.

It’s worth mentioning, at this point, that Bedard was not the only high value left-handed pitcher on the trade market that off-season. The Minnesota Twins were also shopping their ace, the aforementioned Santana.

Santana was one of the best pitchers in the game. By 2008, he had already won two Cy Young awards, been invited to three All Star games and won a Gold Glove. But he was also entering the final season of team control and was going to command quite a bit more money than Bedard would. Eventually, Santana would be traded to the Mets, about a week before the Bedard-to-Seattle deal was announced, and sign a six-year, $137.5 million deal.

The Mets gave up the following: 22-year-old outfielder Carlos Gomez, 18-year-old pitcher Deolis Guerra, 25-year-old pitcher Phillip Humber and 22-year-old pitcher Kevin Mulvey. Depending on where you looked at the time, these were four of New York’s top seven prospects. It was a heavy price to pay for one of the best pitchers of a generation.

So, since it is apparent that Bedard was not going to sign an extension with Baltimore, and the Orioles weren’t going to let the chance to improve their minor league ranks go by, and that the proposed trade with the Reds was probably a little too big of a swing, it is possible that the O’s could have ended up with something like the package that the Twins received for Santana. After all, the Mets were clearly in the market for pitching, and were even said to have checked in on Bedard at the time.

Gomez would go to play just two seasons for the Twins before he was, oddly enough, traded to the Milwaukee Brewers in exchange for shortstop J.J. Hardy. But all things considered, Gomez had a nice big league career. He was outstanding in 2013, slashing .284/.338/.506 with 24 home runs and a Gold Glove to boot. You could make the argument that, at his absolute best, Gomez was better than Jones. However, Jones was far more consistent and maintained a high level of play for several seasons while Gomez had a much shorter peak.

Humber kicked around the bigs for a few seasons. His breakout season came in 2011 with the White Sox, when he posted a 116 ERA+ over 163 innings of work, but he largely struggled, accumulating just 0.9 bWAR over parts of eight seasons in MLB.

The other two pieces included, Guerra and Mulvey, have made it to the majors but failed to impress. Guerra, now 31, is currently on the Phillies 40-man roster. Mulvey, nearly 35, has been out of affiliated ball since 2012.

A Bedard trade was inevitable, and considering the type of prospects that were being thrown around at the time, the Orioles were going to land at least one steady major league contributor. But they got lucky to land a franchise cornerstone in Jones in addition to a longtime starter in Tillman along with a couple of other valuable pieces.

As for the Mariners, maybe they would have been better off going with Plan B, signing Josh Fogg, handing the right field job to Jones and giving Tillman a bit more time to develop.