Slugger Matt Holliday had turned down every offer the franchise had put before him and agent Scott Boras. Reports said that the Rockies offered Holliday $72 million over four years, which Holliday turned down because he did not feel that it was long enough. It was becoming clear that Boras and Holliday were determined to see how much money they could get on the free agent market.
While Holliday was still under the Rockies control for the 2009 season, O'Dowd and Rockies ownership did not want to see Holliday walk away and the team get nothing in return.
If Holliday was the only All-Star that the Rockies were going to lose it may have not been the worst thing in the world. However, three-time all-star Brian Fuentes, the club's all-time saves leader was heading into free agency. The Rockies had talks about a two-year, $16 million deal with Fuentes, but at the time it looked as if the lefty would command somewhere around $30 million on the open market, which made his choice to leave seem simple.
After a season in which the Rockies did a miserable job of defending their National League crown from 2007, the Rockies looked to be hitting their all time low. Not only were they going to lose their best hitter and their all-time saves leader, the future of the most decorated player in franchise history, Todd Helton, was in serious doubt. Helton was about to undergo a back surgery in which discs in his lower back would be fused together.
If losing those three players was not enough, it was becoming clear that former ace Jeff Francis, a 17 game winner in '07, would potentially need a surgery that would put him on the shelf for the '08 season.
At this point, the Rockies were looking at losing their best four players, something that would be devastating to any team.
With O'Dowd heading into the final year of his contract and no talks of an extension, it would have been easy for O'Dowd to pout about ownership not willing to open their wallet and let him spend some money to either keep the players the Rockies had grown, or pay to get some quality free agents.
It would have been easy to give up on being competitive in '09 and plan on it being a rebuilding season for Colorado.
Instead, O'Dowd found a way to make the team even better than they had been in '07.
On November 12th, O'Dowd dealt Holliday to the Oakland A's in exchange for Greg Smith, a crafty lefty who projected to be a solid member of the rotation, Carlos Gonzalez, a potential five-tool player who struggled in his Major League audition in '08, and a former Rookie of the Year closer in Huston Street.
The deal drew the wrath of fans and members of the media. Most felt that O'Dowd should have waited longer into the offseason before dealing Holliday so that teams would get desperate and give up more for him. Others felt that they should have held on to Holliday at least long enough to see if the team could contend in '09, but most were calling for O'Dowd's head because they felt that the A's completely fleeced the Rockies in the deal.
While Holliday struggles in Oakland, hitting .276 with only eight home runs going into Tuesday night, Street has been nothing but dominant for the Rockies. Street lowered his ERA to 2.65. Before a June in which the Rockies launched themselves back into contention, reports were saying that if Colorado were to deal Street mid-season, that the package they would get in return for just Street would be significantly better than what the A's would get for Holliday.
While Gonzalez and Smith have not fulfilled their expectations to date, just the fact that Street has been dominant has experts saying that the Rockies were the ones laughing at the time of the trade.
The Holliday trade, however, was not the end of the offseason moves for O'Dowd.
He had replaced his closer, but still needed insurance in case Francis was not ready to go at the beginning of the season. In Chicago, the Cubs had grown tired of up-and-down fifth starter Jason Marquis. Despite winning 11 games, Marquis had been left off the postseason roster.
It was clear that both the Cubs and Marquis needed a change.
O'Dowd found a way to convince Cubs general manager Jim Hendry to deal Marquis to the Rockies for embattled reliever Luis Vizcaino. Vizcaino had been terrible in his lone season in purple, he went 1-2 with a 5.28 ERA. Lefties hit a robust .372 against him, hitting eight home runs. The numbers were not the only problem for Vizcaino. He repeatedly complained about a lack of time on the mound, thinking that he should be in the game in more high pressure and late inning situations.
If getting Marquis for Vizcaino was not enough of a steal for the Rockies, O'Dowd even got the Cubs to pay some of Marquis' '09 salary.
While Vizcaino pitched in only four games before being released by the Cubs, Marquis has been phenomenal for the Rockies. Going into Tuesday night he lead all of the major leagues in wins with 11. On Sunday he was picked to represent the National League in the All-Star game next Tuesday.
Without Marquis, who has won eight games this season following a Rockies loss, this team would be nowhere near contention. With him they sit just two games out of the Wild Card, and within striking distance of the Dodgers in the National League West.
O'Dowd has legions of critics. He is the fourth longest tenured general manager in the Majors. Much of the criticism is deserved. O'Dowd failed miserably in his first major decisions with the club. He will long be remembered as the general manager who gave Denny Neagle $55 million over five years and Mike Hampton $128 million over eight years before the 2001 season. Hampton won just 21 games for the Rockies and reshaped the way the Rockies look at building their team.
It sent the Rockies into a four year rebuilding plan, which saw them put players like Jose Hernandez and Desi Relaford on the field on a regular basis. In 2005, the opening day left fielder was named Kit Pellow.
While fans had every right to be critical of O'Dowd, they must now acknowledge that he has built a team that has a chance to win every single night despite losing their best hitter, their all-time saves leader, and their ace in one offseason.
With O'Dowd entering the final half of the final season of his contract, and the Rockies in the thick of contention, Rockies ownership needs to acknowledge that O'Dowd has done a phenomenal job of evaluating talent and finding ways to keep a mid-market team competitive.