As Ryan Dempster continues to pitch well, and as the Cubs continue to look like a team that, while plucky, probably aren’t going to seriously contend for a playoff spot come September, Dempster’s name will continue to bounce around trade rumor circles.

From Ken Rosenthal:

Cubs right-hander Ryan Dempster, an obvious trade candidate, would be even more likely to be moved if the team signed righty Matt Garza to a contract extension.

Keep in mind, though, that Dempster, 35, effectively would control the process. As a player with 10 years of major-league service, five with the same club, he has the right to veto any deal.

Dempster, earning $14 million in the final year of his contract, is eligible for free agency at the end of the season. He likely would consider any proposals on a case-by-case basis, with the usual variables coming into play.

Players typically require inducements to waive their no-trade protection, either in the form of a cash bonus or contract extension. Dempster, though, already would cost nearly $5 million for two months unless the Cubs included cash in the deal to “buy” better prospects.

The Cubs might need to do just that — under the new CBA, potential free agents traded in the middle of a season no longer are eligible for draft-pick compensation. The new rule diminishes their trade value; the acquiring teams no longer can count on getting a draft pick, or picks, to replace the prospects they lost.

The CBA point is an important one, as Dempster – assuming he keeps pitching well – would have been a candidate to be made a one-year, qualifying offer (about $12.5 million) after the season ends. And, given that he’s probably looking at one last decent free agent score, he probably would have declined. That would have made him much more valuable in the trade market.

As it stands, the only team eligible to make such an offer to Dempster is the Cubs, if they keep him. The draft pick compensation would be nice, but keep in mind: whereas Dempster would likely reject such an offer from the other 29 teams, are we certain he would reject it from his adopted hometown team?

That must weigh in the calculus of the Cubs’ decision on whether or not to trade Dempster. The acquiring team is getting a true rental player – possibly a very good one, but a rental player just the same – and that value may not exceed whatever value Dempster (plus the possibility of compensation) has to the Cubs. In that scenario, the Cubs might elect to hold onto Dempster, even if they know they don’t want to re-sign him, and even if they know they have no chance at the playoffs in 2012.

This, of course, all ignores Dempster’s no-trade rights, which, as Rosenthal points out, could be exercised and leveraged in any number of ways.

As I’ve said before, the ideal outcome here is that Dempster wants to go to a contender, and the Cubs can pick up a couple prospects in a deal (perhaps one in which they include some cash to incentivize the trading team to up the prospect bounty). That would remove the uncertainty attached to the decision about whether to make a qualifying offer to Dempster in the offseason, or to sign him to a new deal.

Finally, I have to disagree with Ken on the presumption that a Matt Garza extension makes trading Ryan Dempster more likely. I see it as neutral, or possibly in the other direction. As we’ve recently discussed, signing Garza to an extension may signal the Cubs’ intention to build a contender in the next two years, which could make the Cubs more willing to bring Dempster back on a short-term deal. Further, if the Cubs don’t extend Garza, and instead trade him for prospects, wouldn’t that make them more likely to trade Dempster?



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