There was a time when a certain kind of small business owner — strapped for cash — with a meager promotional budget, easily could be tempted to adopt a “clever” name, as a “short-cut,” to “play off” a well-known, iconic brand, but in the end, he or she probably was convinced by counsel that doing so would be foolish: It would be certain to draw a long, distracting, losing, and costly fight.

One tried and true way of effectively steering a business to avoid this kind of fire has been to have it “put the shoe on the other foot.” In other words, having those involved answer the hard question of what they’d honestly do if they managed the famous brand in question and someone came along doing exactly what they are proposing to do. Often yielding: “Oh, now I get it.”

Nowadays though, with the hungry media’s fascination over the ever-popular “trademark bullying” accusation, the juicy David v. Goliath story-lines, and the prevalence of mysterious litigation settlements with undisclosed terms, as well as a growing appreciation that large brand owners would prefer to avoid the shaming label altogether, there is a growing and legitimate concern that small business owners may be more and more inclined to bait large brand owners into fights for the publicity — to help launch their new product — and eventual confidential settlement.

If not actual bait, then at least these David-style “benefits” unfortunately appear to be factored into the trademark decision-making under the present trademark landscape.

Now, I certainly don’t know the true motivation behind the latest trademark to trigger an iconic brand owner’s legitimate objection, but based on what I’ve seen thus far, I do tend to believe that the latest brand to undeservingly wear the pejorative and media-baiting “trademark bully” label is: Tootsie Roll.

Over the weekend, CNNMoney reported the filing of a trademark lawsuit by Tootsie Roll Industries, LLC, owner of the more than century old Tootsie Roll confection brand, against Rollashoe, LLC, a small business based in Miami Beach, Florida, selling women’s footwear under the Footzyrolls name and mark.

The owners of Rollashoe, were quoted applying the trademark bully label to their adversary:

“This lawsuit it completely frivolous and has no merit,” Rolloshoe owners Sarah Caplan, 28, and Jenifer Caplan, 34, said in a statement. “This is just another example of Tootsie Roll trying to bully a minority-owned women’s small business.”

I couldn’t help but notice the absence of quotes that the Caplans were shocked to hear from Tootsie Roll. Didn’t the Caplans have to know they were walking into a serious fight with a major brand owner?

And not a frivolous trademark fight either: Tootsie Roll is a federally-registered trademark for clothing, a popular Halloween costume for babies and adults, the Tootsie Roll brand has been around more than 100 years, sixty-four million Tootsie Rolls are produced each day, and “tootsie” has a widely-known meaning for a person’s foot, putting aside the fact that the iconic Tootsie Roll brand is likely famous and trademark dilution requires no likelihood of confusion.

Giving the Caplans the benefit of the doubt, perhaps they had never heard of trademark dilution before, and maybe they truly thought confusion was the test and impossible.

Yet, at the close of 2010, Tootsie Roll reported to shareholders record sales of $517 million, as detailed in its Annual Report, specifically noting: “Our key competitive advantage lies in our well known brands . . . .” It also identified “candy buying mothers 25-44 years of age, [as] a key Tootsie Roll demographic group.” These facts aren’t surprising and neither is Tootsie Roll’s objection.

Tootsie Roll wasn’t exactly trigger-happy on this one either, having expressed concern about the FOOTZYROLL mark back in 2009 and formally opposing registration of the mark in early 2010; it held off seeking injunctive relief in federal district court until now.

Again, when you’re tempted to mechanically apply the “trademark bully” label to a brand owner’s particular enforcement effort, it might be a good idea to ask the brand owner’s enforcement target what it would be like if the shoe were on the other foot.

Has anyone bothered to ask the Caplan sisters if they were surprised to hear from Tootsie Roll, and what they’d honestly do if the shoe were on the other tootsie?