Could The Cubs Make a Push For Roy Halladay?

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Could The Cubs Make a Push For Roy Halladay?
(Photo by Morry Gash-Pool/Getty Images)

As trade rumors intensify around the Blue Jays' ace Roy Halladay, the odds of him moving appear to be rising.

However, the odds of Toronto receiving the crop of young talent they desire seems to be shrinking by the day. In the current economy, teams are trying to build winners more than ever before, and moving three or four top tier pieces just doesn't make sense to most franchises.

For a team that's playing within an equally shrinking window of opportunity, especially one that has created a concrete ceiling over their farm system by overpaying veteran free agents over the last six years, would selling a few of their top pieces make sense?

For the Chicago Cubs, it might.

On Sunday, the Cubs needed an emergency start from Kevin Hart because of Ryan Dempster's toe issue and Ted Lilly having some leg issues of his own. Hart, one of the top names in the Cubs organization for the last couple seasons, looked strong against Washington, hitting 94 mph with his fastball and seeing a peak of 89 mph on his slider.

Which got me to thinking: do the Cubs have enough pieces to make a bold move for someone like Halladay?

Obviously back in March the Cubs were heavily involved with the San Diego Padres in trade talks surrounding another elite pitcher, Jake Peavy. In March, San Diego General Manager Kevin Towers didn't think the Cubs had enough to make a deal happen.

Let's talk about what we've seen from the Cubs prospects in the majors this year.

Hart, albeit in limited action, has looked sharp and, at times, able to overpower major league batters. Granted, Sunday was against the Nationals, but it doesn't diminish the movement and velocity his pitches showed.

Randy Wells, though he didn't have his best stuff against the Nationals on Saturday, has been one of the top rookies in the National League this season. He's now 5-4 with a 3.00 ERA and an impressive 1.15 WHIP. He has also qualified for a quality start in almost all of his starts this year, something Toronto would have to see as a plus in moving their ace.

Either of these young starters could be a centerpiece for a package with Toronto.

Also available in a trade for Halladay could be Rich Harden. Harden's in the final year of his contract and the Cubs would likely want to move the remainder of his salary off the books in any deal. He would at least give the Jays a top of the rotation starter for the remainder of this season.

Right now, the Jays have Kevin Millar hitting under .230 with a .309 on-base percentage as their primary designated hitter, and have health concerns about Scott Rolen at third base.

Enter Jake Fox.

Fox has done everything the Cubs organization could have hoped for when Aramis Ramirez went down with his shoulder injury two months ago. And now that Ramirez is back, Cubs manager Lou Piniella is going to struggle to find one of his hottest hitters consistent playing time.

For the year, Fox is batting .326 with five home runs and 19 runs batted in, and has a .365 on-base percentage in his 86 at bats.

He makes consistent contract and has shown good power in his limited action, making him a cheaper and more effective DH than Millar. And, at just 26-years-old, could contribute for the Jays for years.

The biggest concern the Cubs would have to mitigate is their current payroll situation. The whispers from the organization to the Chicago media have been, since last November, that the Cubs couldn't add a significant piece of salary to the books with the sale of the team still pending.

That's why Cubs General Manager Jim Hendy "was forced" to trade popular utility man Mark DeRosa to Cleveland before signing Milton Bradley; Bradley's contract is backloaded and full of incentives, the only ways it would work for the Cubs payroll between ownerships.

Halladay is making $14.25 million in 2009 and is due $15.75 next year. Obviously any team that acquired the All Star would want to lock him up for longer than just next season, so an extension somewhere in the neighborhood of $18-20 million per season is likely.

This wouldn't be easy for the Cubs, but might be possible.

The Cubs already have an uber-expensive starter signed long term in Carlos Zambrano. They are also on the hook to pay Alfonso Soriano $18 million through 2014, which doesn't help. But there are some dollars coming off the books that could play a role into the Cubs making a move for Halladay.

First, Ted Lilly, the team's lone All Star this year and one of Halladay's former teammates in Toronto, has a contract expiring after 2010 as well. That would open up $12 million off the Cubs' cap number in 2011.

Perhaps the harder decision could come around one of the other popular veterans on the Cubs roster, Derrek Lee.

Lee is having a wonderful, resurgent season and has carried the Cubs through Ramirez's absense. But, like Lilly and Halladay, his contract expires after 2010. His $13 million salary would likely stay off the books if an extension was worked out with Halladay, meaning the Cubs would be looking for a new first baseman in 18 months.

So the real question at the heart of the Cubs decision making at the July 31 trade deadline is how hard they want to push for a championship in the two Octobers.

Is it worth a chunk of free agents to have arguably the best 1-2 starting pitcher duo in baseball? Is it worth the reality that the Cubs would be without Lilly and Lee after next year to shoot for the moon now? Is Halladay the missing piece that could end 101 years?

If so, it might be time for Hendry to dial a Canadian number.

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