As investors are eagerly watching to see where the market goes for the rest of the second half of the year, Art Cashin says he's skeptical the current rally will hold. Several investors have said stocks found a bottom in mid-June and could be on their way to the next bull market. Others see this as a lengthier bear market bounce compared to those the market has seen throughout the year, with a chance to fall again before the year is up. "This bear market rally, if it is such, and I believe it to be, has certainly lasted longer than any of the rallies so far this year," the director of floor operations for UBS Financial Services said on CNBC's "Squawk on the Street" Monday morning. "The fact that we have gotten pretty close to a 50% retracement in some areas would favor the bulls – and the fact that when you get there, that becomes a rarer event to roll back and retest the lows, yet I still believe that that will happen." "In the year of interim election, a second year in a presidential term, the lows tend to come a little bit later in the year, probably going into mid September," he added. "So the numbers that I'm looking at, the way I'm looking at the economy – I still think it's a bear market rally but I am perplexed by ultimate the staying power that they have had." On Friday the S & P 500 closed above 4,231, the 50% retracement from its peak to trough. BTIG technical analyst Jonathan Krinsky has said a close above that level would mean this is a new bull market and not merely a bear market bounce. The S & P 500 gained 9% in July and, as of Friday's close, was up 3.6% for the month. "The VIX being now where it is distresses me further, that tells me that we're in the intermediate term overbought," Cashin said. "I thought we might be topping out about three or four sessions ago." The VIX, or the CBOE Volatility Index, measure's the stock market's expectation of volatility. It has come off its most recent mid-June highs and now is trading around its long-term average of 20. Stocks have been trading in lockstep with the index , which is contrary to the way typical market rallies have played out over the past several years. "I do think there's further contraction," Cashin said. "The Fed is going to have to tighten things up and we're going to have to see some pullback in employment. That's going to cause pain and I think that will help this rally roll over." —CNBC's Jeff Cox contributed reporting.