Beware the ides of March, or any month in 2015, Bill Gross said on January 6. At that time the S&P (SPX) was near a 2015 low of 2002.61 when he proclaimed what should be the first of his predictions to be tracked in his ongoing bid to challenge his one-time “bond king” trading mantle. But in this bid to regain his thrown, will he change is trading strategy? We look to his recent letter for clues.

Since making that pronouncement stocks, measured by the S&P, bounced to near 2062 before falling to trade near 2008 today.

Bill Gross at the Morningstar, Inc. (NASDAQ:MORN) conference in Chicago – June 19th 2014

Bill Gross notes the social stigma associated with going against the crowd

In the analysis, Bill Gross noted the difficulty of calling a market top, citing . Why, the social stigma associated with going against “the crowd,” a task he accurately noted “behooves an individual with a reputation at stake to stand clear.”  But Gross is a man who has risen above the confines of the economic controllers. He is his own man and is willing to challenge the powerful establishment because “moving out of the way has never been my style.”

What is the Bill Gross “style” is an investment template similar to derivatives master and mathematical value guru Ray Dalio of Bridgewater Associates as well as Martin Barnes of the Bank Credit Analyst, Gross said in the letter, potentially providing clues to the next question that should be asked with Gross: is his trading methodology trading now that the decades long bull market in bonds appears to be hitting a wall near zero?  With interest rates at an all time low, measured by the U.S. ten year note trading near 1.8 percent, and many quantitative models pointing to future volatility, does the Bill Gross investment method change at its core?

That question remains to be answered, but Bill Gross did not how the world was changing, particularly with regarding the U.S. Federal Reserve. “Each downward spike in the economy and its related financial markets was met with additional credit expansion generated by lower interest rates, financial innovation and regulatory easing, or more recently, direct central bank purchasing of assets labeled ‘Quantitative Easing,’” Gross noted. He then pointed to the new normal of “secular stagnation” and an “Alice in Wonderland” environment.

Bill Gross on credit increasingly behaving as a multiplicative power of monetary expansion

There are challenges, Bill Gross notes. “It is becoming obvious that as yields move closer and closer to zero, credit increasingly behaves like cash and loses its multiplicative power of monetary expansion for which the fractional reserve system was designed.”

Bill Gross is discussing historic shifts in the management of economic policy, as he notes the search for yield.

This new environment actually discourages investment, he says, Investment due to declining rates on return.  As a result financial asset structures such as money market funds, banking, insurance, pensions, and even household balance sheets “malfunction as the historical returns necessary to justify future liabilities become impossible to attain. Yields for savers become too low to meet liabilities.”

What Bill Gross is describing are threatening both the real and the finance-based economies. “It’s as if the rules of finance, like the quantum rules of particles, have reversed or at least negated what we historically believed to be true.”

These are big thoughts, but the question is: Does the Bill Gross trading strategy change in light of the shift in macro market environments? While he provides several reasons to do so in his recent letter, that direct question has yet to be answered.

To read the full letter, click here.