Howie Carr’s jump from WRKO-AM (680) to WTKK-FM (96.9) isn’t a done deal just yet. Carr’s new morning drive-time show is supposed to begin in October. But after the Herald reported this past Monday that Carr was poised to bolt WRKO, station spokesman George Regan released a statement hinting that WRKO might take legal steps aimed at keeping Carr from leaving — or, barring that, at making his exit as unpleasant as possible. “He is a tremendous asset to WRKO and Entercom [WRKO’s parent company] has every intention of retaining his services for many years to come,” said Regan. “Any report suggesting a change is incredibly premature.”

If the station has a case, it probably hinges on a clause in Carr’s contract that gives WRKO the right to match any competitor’s offer. But on Tuesday, Carr filed a pre-emptive lawsuit of his own, accusing WRKO of repeatedly declining to extend his contract, and arguing that any provisions aimed at keeping him from leaving for a competitor were legally unenforceable.

Whether the courts will agree remains to be seen. But even if they don’t, WRKO should think twice about mounting a fight. Carr’s relationship with WRKO seems to have been seriously strained even before this dust-up hit the headlines; now that things have reached this point, it’s hard to imagine the station and its marquee talent making peace.

One source with knowledge of the situation says that Carr — whose populist conservatism runs the gamut from witty erudition to juvenile mean-spiritedness — had accumulated a long list of grievances with WRKO. Among other things, he was concerned about the station’s declining ratings; he felt management wasn’t promoting or syndicating him effectively; and he bristled at being pre-empted for preseason Red Sox games, which WRKO began broadcasting this year in an awkward joint-broadcasting arrangement with WEEI-AM, Entercom’s Boston sports station. “Howie’s overall feeling is that it’s a poorly run operation,” this individual, who works in Boston radio, tells the Phoenix.

This casts a new light on the alleged feud between Carr and Tom Finneran — the ex–Massachusetts House Speaker who, after pleading guilty to perjury in a legislative-redistricting case, took over WRKO’s morning-drive-time slot earlier this year. In March, the Herald turned this purported beef into a cover story, reporting that Carr (who’s also a Herald columnist) was incensed after Finneran joked that he should be killed and stuffed in the trunk of Governor Deval Patrick’s car. At the time, I argued that the whole flap seemed to be a shameless publicity stunt. In retrospect, though, Carr’s stagy wrath may have obscured genuine frustration: a strong morning host would have helped Carr’s own ratings and market position by driving listeners to the station. But Finneran clearly wasn’t ready to fly solo — and hasn’t been given a reliable sidekick to help him along.

More significantly, Carr’s disenchantment and potentially imminent departure also raise questions about Entercom executive Jason Wolfe, who went from running WEEI’s programming to directing programming for both WRKO and WEEI in early 2006 and has been considered something of a golden boy in local radio circles. Given WEEI’s continued success, the underwhelming performance of WRKO under Wolfe’s watch is especially striking. Former hosts Scott Allen Miller and John DePetro are gone. Finneran is struggling in the morning drive-time slot, both in terms of ratings and in terms of establishing a compelling on-air persona. It’s still not clear how splitting the Red Sox between WEEI and WRKO helps either station. And now Carr — the station’s name-brand talent — is poised to bolt to its major competitor. (Wolfe and Julie Kahn, Entercom New England’s vice-president and market manager, did not return calls from the Phoenix.)

If and when Carr starts broadcasting from WTKK’s studios, he’ll be going head to head with Finneran, which will make the ex-Speaker’s already dicey situation even more precarious. “It’ll make for an interesting battle because of the personal hostility between the two men,” says Michael Harrison, publisher of Talkers magazine. “But there’s no question in my mind that Carr is the more accomplished.” Being on the FM spectrum also stands to expand and diversify Carr’s listener base, Harrison adds: “FM talk is the coming wave, and new people might discover him who otherwise don’t hang out on the AM dial. There are a lot of young people on the FM dial, a lot of women.”

And let’s not forget the bottom line. Carr’s current salary at WRKO is unknown. But based on what comparable hosts have made here and elsewhere, it’s likely that he was at or over $300,000 — and that WTKK plans to pay him significantly more. Nice work if you can get it.

The permanent PR problem
Unlike some of my media-watching colleagues, I’ve never borne any ill will for Globe transportation reporter Mac Daniel; in fact, I think his Sunday “Starts & Stops” column is pretty good. Still, it was hard not to raise an eyebrow at the news that Daniel was leaving journalism to become communications director for the Massachusetts Turnpike Authority — which, as the Globe itself noted, he’s been covering for the past five years.