With a strong correlation between the yen's movements and the Nikkei, "the lower the dollar-yen goes, the lower the Nikkei is going to go as well," Schlossberg said.
The Nikkei, which soared almost 57 percent last year amid aggressive monetary stimulus from the Bank of Japan and a weak yen, has tumbled 14 percent so far this year, making it one of the worst-performing major markets.
Schlossberg has been closely watching U.S. Treasury yields, which have been hovering just over 2.5 percent.
"If U.S. rates go below 2.5 percent on the 10-year (Treasury), there's a very strong possibility the dollar-yen will go below 100," he said.
Read More Why tapering didn't push up bond yields
There may not be any relief on the U.S. interest rate front any time soon. While many analysts expected Treasury yields to rise as the U.S. Federal Reserve tapered its asset purchases, they've actually slipped since tapering began in January and some expect the trend may not change.
"The bottom line is people still want yield," Sheila Patel, head of international at Goldman Sachs Asset Management, told CNBC. "You still have huge amounts of pension money around the world and retirement savings (and) people in the aging curve of the demographic. They need fixed income and the bellwether of fixed income is still U.S. Treasurys," she said.
Read More More BOJ stimulus soon? Don't bet on it
So far this year, dedicated long-term U.S. government bond mutual funds and exchange-traded funds (ETFs) have seen $4.65 billion worth of inflows, according to Jefferies data. Overall, U.S. bond funds have seen $49.32 billion worth of inflows this year, the data show.
All of these flows are working to keep U.S. yields low and weighing on the dollar and by extension may be frustrating Abenomics, or the more than one-year-old plan from Prime Minister Shinzo Abe to kick-start Japan's long-moribund economy. One of Abenomics' aims was to weaken the yen to combat deflation, partly via a massive easing program from the Bank of Japan.