But then again, to Westbrook, the comfort of knowing where he'd be the next few years was worth a look, too.
With that comfort in mind, Westbrook agreed to the Indians' offer of a three-year contract extension through the 2010 season. The extension, which was announced Friday, is valued at $33 million, some of which will be frontloaded into the $6.1 million Westbrook was already set to make this season.
The deal does not include any option years, but general manager Mark Shapiro, declining to go into specifics, said it does include "significant" trade protection.
"We never do a strict no-trade clause," Shapiro said. "But recognizing how much Jake wanted to be here and how close he was to some alternatives [in free agency], we recognize that in trade protection."
The Tribe is still in talks with designated hitter Travis Hafner, who will be eligible for free agency after the 2008 season, about an extension. Shapiro, though, wanted Friday's spotlight to be on Westbrook and said he would update the media on the status of the Hafner talks later this weekend.
With the signing of Westbrook, the Indians avoided the threat of spending this fall making a late effort to keep their No. 2 starter.
In Shapiro's estimation, keeping Westbrook was as much a matter of gut as it was brains.
"I remember walking with [New England Patriots vice president of player personnel] Scott Pioli during Spring Training, and we were talking about player contracts," Shapiro said. "He said, 'There are times when you have to put analysis and statistics aside and ask yourself if it's a guy you want to bet on."
So Shapiro and the Indians put their money on Westbrook, who has been one of the Tribe's most consistent pitchers over the last few years.
Though he flies low on the national radar, Westbrook's 44 victories between 2004-06 were tied for fifth-most among American League pitchers, behind Johan Santana (55), Kenny Rogers (49) and Jon Garland (48). He's one of just four AL pitchers to post at least 14 wins in each of the last three seasons, joining Santana, Rogers and teammate Cliff Lee.
Just as importantly, the 29-year-old Westbrook, who is in his seventh season with the Indians, has been remarkably durable over the last three years. He pitched at least 210 2/3 innings in the 2004, '05 and '06 seasons.
"That's no coincidence," Shapiro said. "That comes from his conditioning and how he takes care of his body. There's not a guy in that clubhouse who will outprepare him."
The Indians first prepared their offers to Westbrook during Spring Training, and the two sides decided they had enough momentum toward a deal to continue talks into the season.
A few days into the season, assistant general manager Chris Antonetti, who negotiated with Westbrook's agent, Michael Maas, began to get a good feeling a deal would be consummated.
"Because of his desire to be here and his willingness to make some concessions towards us," Antonetti explained. "Once we had that, we had enough common ground to get a deal done."
Westbrook admitted the contract discussions weighed on his mind during Spring Training and between starts in the early going this season, in which he has gone 0-1 with a 7.36 ERA in two starts.
But the easy part of the process for Westbrook was deciding that he'd like to remain in Cleveland.
"It comes down to how comfortable I am here," he said. "Not only for myself, but my family. We have an 18-month-old son [Parker] growing up. We felt very comfortable here, and [the Indians] made a huge effort to get the number I wanted."
The $33 million number was nice, but so was the number of years.
Westbrook has been traded three times in his career, including the 2000 trade that brought him to Cleveland as a player to be named in the David Justice deal, so he values consistency in address labels.
"The Indians have stuck with me," he said. "They've really had confidence in me to go out and get the job done."