Baltimore Orioles: How Scott Rolen was Almost an Oriole

St. Louis Cardinals v Pittsburgh Pirates
St. Louis Cardinals v Pittsburgh Pirates / George Gojkovich/GettyImages

On Tuesday, the BBWAA elected Scott Rolen into the Baseball Hall of Fame. The legendary third baseman played 17 seasons with the Philadelphia Phillies, St. Louis Cardinals, Cincinnati Reds, and Toronto Blue Jays. Before the Phillies dealt Rolen to the Cardinals at the 2002 trade deadline, baseball history was almost altered when the Baltimore Orioles nearly acquired him in the 2001-2002 offseason.

Things were looking bleak for the Orioles. In June of 2001, Cal Ripken Jr. announced that the current season would be his last, leaving a huge hole in the team. After their fourth straight losing season, the Orioles needed a big move. Outfielder Marty Cordova was brought in to replace the aging Brady Anderson, who was released earlier in the offseason. He'd go on to have a solid season with the O's. But a replacement for Ripken was needed. The Orioles set their sights on Phillies' third baseman Scott Rolen.

The Baltimore Orioles could have landed a new franchise cornerstone

Rolen was entering his age-27 season and was already a 3x Gold Glove winner. He was also entering his final season under contract. The Phillies tried to extend Rolen, but he had already turned down a 7-year, $90MM offer (per The Washington Post in 2001). ESPN later reported in 2002 that the Phillies actually offered him as much as 10-years and $140MM in November of 2001. Rolen forced GM Ed Wade's hand. Despite coming off of an 86-win season - their best since 1993 - the Phillies were open to moving the former Rookie of the Year.

Described by The Baltimore Sun as a nine-player mega deal, the Orioles were willing to move a lot of pieces to land their new third baseman. The Phillies submitted an offer that would send Scott Rolen, RHP Chris Brock, INF Kevin Jordan, and an unnamed prospect to the Orioles, in exchange for INF Jeff Conine, LHP Buddy Groom, RHP Sean Douglass, RHP Sidney Ponson, and top pitching prospect Erik Bedard. Bedard, 22, was ranked by Baseball America as the 90th best prospect in all of baseball and the top prospect in a barren Orioles' farm system in 2002.

There were a few snags that held up the deal. First, the Orioles were unwilling to part with both Bedard and Douglass, who the Orioles valued as their top pitching prospects. Douglass, 22, flashed some talent as a starter in the minors, but lasted just five seasons with the Orioles and was waived in 2003. The Orioles modified the offer, substituting a different prospect for Bedard, but it wasn't enough to get the deal done. The Phillies' interest seemed to hinge on acquiring Bedard. The Phillies also asked about the young and blossoming Jay Gibbons, but he was not heavily considered. Second, and perhaps more importantly, Rolen was set to hit free agency after the 2002 season and prior attempts to extend him were unsuccessful. According to The Baltimore Sun, GM Syd Thrift believed a potential extension would cost $150MM over 10 years. At the time, it would have been about the 12th most expensive deal by AAV. Owner Peter Angelos said, "forget it." Whether an extension would have been done is a mystery, but Angelos nixed any potential deal.

The aftermath of the nixed deal

The Phillies held onto Rolen through the offseason before trading him to the St. Louis Cardinals at the 2002 trade deadline for 3B Placido Polanco, SP Bud Smith, and RP Mike Timlin. Timlin was unremarkable in Philadelphia, while Bud Smith never pitched a single inning for the major league team. The centerpiece of the deal was Polanco, who played parts of four seasons with the Phillies before being dealt again to the Detroit Tigers. He'd rejoin the Philies in 2010 for a three-year stint including an All-Star nod and a Gold Glove.

The Phillies would not have been much better off settling for a compromise with the Orioles. Chris Brock was sent to the Orioles in a separate deal, pitching in just 22 games with the team, while Kevin Jordan was released later in the offseason. As for the return, Sidney Ponson would bounce around with 7 different teams in 8 years of mediocre ball; Sean Douglass pitched his final game in 2005; Buddy Groom had an exceptional 2002 season, but retired in 2005 after his age-39 season; Jeff Conine was one of the Orioles' best hitters in 2001, but he was also 36 and went on a decline in the following years. While it's unknown who the Orioles offered in place of Erik Bedard, they were wise to withhold Bedard from the trade if at all possible. Bedard finished 5th in AL Cy Young voting in 2007, his final season with the Orioles. The Orioles traded Bedard in the 2007-2008 offseason to the Seattle Mariners for a package of pitchers Chris Tillman, George Sherrill, Tony Butler, and Kam Mickolio, as well as outfielder Adam Jones. Tillman was an important part of the Orioles' playoff runs in the 2010s, while Adam Jones was a 5x All-Star and 4x Gold Glove winner who hit 263 HRs with 1,781 hits in 11 seasons with the Baltimore Orioles.

Is this a lesson in "prospect hugging," holding onto potential rather than proven talent? Not necessarily. While the inclusion of Erik Bedard held up the deal for both sides, Orioles owner Peter Angelos was simply unwilling to pay Scott Rolen what was necessary to extend him, and while the team was given a 48-hr window to negotiate an extension before the trade, there was never going to be a deal as Scott Rolen seemed to prefer free agency (per The Washington Post). Rolen would later sign an 8-year, $90MM deal with the St. Louis Cardinals, where he helped to win the 2006 World Series.

Had the Orioles been able to sign Rolen to a 10-year extension, it would have worked out fairly well. Rolen played 1,202 games in his next 10 seasons, hitting .281/.360/.485 with a .846 OPS, 121 OPS+, and 175 home runs. He also put up 114 DRS and 43.9 rWAR. While he did miss portions of most seasons - playing in 140+ games in just three different seasons - he remained a valuable player for the rest of his career. Even as his bat began to deteriorate, Rolen's defense was strong to the end, posting a 10 DRS season at age-36. He won his 8th and final Gold Glove in 2010 at 35.

Rolen got his happy ending. So did the Baltimore Orioles, as they got two good years of Erik Bedard before finally finding their fan favorite star in Adam Jones. It's nice to imagine what Scott Rolen would have looked like on the Orioles, as the 2000s were a decade to forget for Baltimore. Unfortunately, the Orioles were unwilling to move prized prospects for a one-year rental. Rolen may not have moved the needle enough for a team coming off of a 63-98-1 season.

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