The bad news just keeps coming for conservative talker Rush Limbaugh.

Which bulletin was worse, though? The news in April that he was being dropped by WIBC in Indianapolis, a booming talk powerhouse that played home to Limbaugh's radio show for more than two decades, or the news this week that the talker's new address on the Indianapolis dial is going to be WNDE, a ratings doormat AM sports station that has so few listeners it trails the commercial-free classical music outlet in town?

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The humbling, red-state tumble is just the latest setback for the conservative talker who has seen his once-golden career suffer a steady series of losses recently.

Divorced from successful, longtime affiliates in places like New York, Los Angeles, Boston, and Indianapolis, Limbaugh's professional trajectory is heading downward. That's confirmed by the second and third-tier stations he now calls home in those important media markets, and the fact that when his show became available, general managers up and down the dial passed on it. Apparently turned off by the show's hefty price tag, sagging ratings, and disappearing advertisers, Limbaugh continues to be a very hard sell.

It's a precipitous fall from the glory days when the host posted huge ratings numbers, had affiliates clamoring to join his network, and dictated Republican politics. All of that seems increasingly distant now. With his comically inflated, $50 million-a-year syndication deal set to expire next year, Limbaugh's future seems uncertain. "Who would even want someone whose audience is aging and is considered toxic to many advertisers," askedRadioInsight last month.

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For Limbaugh, the troubles were marked by key events from 2012 and 2013. The first came in the form of Limbaugh's Sandra Fluke implosion, where he castigated and insulted for days the graduate student who testified before Congress about health care and access to contraception, calling her a "slut" and suggesting she post videos of herself having sex on the Internet. The astonishing monologues sparked an unprecedented advertiser exodus.

The following year, as the host struggled to hang on to fleeing sponsors, radio industry giant Cumulus Media decided to negotiate its Limbaugh contract in public, making it clear through the press that the company was willing to cut ties with the pricey host in major cities where Cumulus owned talk radio stations. In the end, Limbaugh stayed with Cumulus stations, but the company sent a clear signal to the industry: Limbaugh was no longer an untouchable and general managers weren't clamoring to hire him. Since then, the talker's fortunes have only faded.

Another looming problem? Conservative talk radio is a "format fewer advertisers are interested in buying because of its aging audience," noted radio consultant and self-identified Republican Darryl Parks. Limbaugh himself recently conceded a generational disconnect: "Now that I've outgrown the 25-54 demographic, I'm no longer confident that the way I see the world is the way everybody else does."

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That disconnect may be fueling Limbaugh's waning political influence. Once a mighty player whose ring wasconstantly kissed by Republicans, this campaign season seems to be unfolding with Limbaugh on the sidelines, his clout and his ability to drive the conversation seemingly surpassed by other conservative mediaplayers.

Here's a perfect example. In April, Bloomberg's Mark Halperin conducted an awkward interview with Republican presidential hopeful Sen. Ted Cruz, asking the Hispanic candidate about Cuban food and if he'd answer at least one question in Spanish. Limbaugh immediately castigated Halperin's Q&A on his show, but nobody seemed to pay much attention to his complaints.

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Fast-forward one week and syndicated conservative columnist Ruben Navarrette lodged similar complaints about the interview. (i.e. "This was bad journalism, bad form, and bad manners.") Except this time the complaint went viral and Helperin was quickly forced to apologize.

At BuzzFeed, a writer marveled at how Halperin's controversial interview had gone unnoticed for nine days. But it hadn't gone unnoticed. Limbaugh highlighted the interview right away. It's just that nobody cared about the talker's critique at the time.

Limbaugh's unfolding major-market woes will do little to boost his faltering influence. Last year he was bounced off a high-profile station in Los Angeles, shipped down the dial, and deposited on a has-been outlet (KEIB) that today has trouble securing a 1.0 rating, according to Nielsen ratings.

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Note that his forced farewell from WIBC in Indianapolis was likely painful. The station hosted the talker for 22 years before announcing in April it was time for him to go. Especially embarrassing for Limbaugh was the fact that WIBC is sticking with its conservative talk radio lineup, it just no longer wanted Limbaugh to be a part of it.

Then, after WIBC announced it was dropping Rush, no stations in the market stepped forward to pick him up, which meant Limbaugh then had to be bailed out by iHeartMedia. Formerly known as Clear Channel, iHeartMedia owns the syndication company that produces and sells Limbaugh's radio show, Premiere Radio Networks, and iHeartMedia owns hundreds of radio stations. So with no Indianapolis takers in sight, iHeartMedia was forced to shoe-horn Limbaugh onto its own, lowly rated all-sports channel in the market. (The station will soon be simulcast via a new iHeartMedia FM translator signal in the Indianapolis market.)

"There's no way iHeartMedia would've placed Limbaugh on an owned Sports station if the company had any other affiliation options in the market," noted RadioInsight when the news broke on Tuesday. "But when everyone one else says no and you need to save face, options become limited."

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That same desperate scenario is playing out in Boston, where Premier hasn't been able to find a new home for Limbaugh. This, after WRKO announced it was dropping the show. One station owner recently told the Boston Globe that Premiere had offered the Limbaugh show four times, and four times the station turned it down.

Fact: Years ago station owners lined up for the chance to pick up Limbaugh's powerhouse program.

Now, rumors are still swirling in Chicago that talk radio powerhouse WLS is poised to drop Limbaugh. The move was first reported in March and quickly denied by WLS's owner, Cumulus Media. But Limbaugh's ratings are clearly down in the Windy Cindy. According to a March report in the Chicago Tribune, Limbaugh's WLS show ranks 24th in the market, drawing 121,000 listeners in a metropolitan area of roughly 10 million people.

"The Chicago rumors come as no surprise to me," wrote consultant Parks, "as three different Cumulus executives have told me on different occasions they wish they could get rid of Limbaugh's show and they can't sell it."

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Ratings and revenue. That's what the radio business has always revolved around. These days, Limbaugh's having trouble delivering either.