Based on your financial expertise, provide your response or viewpoint on the given financial question or topic. The response format is open.

When the market price for a stock is below a tender offer's price, is it free money (riskless) to buy shares & tender them?
It is not a "riskless" transaction, as you put it. Whenever you own shares in a company that is acquiring or being acquired, you should read the details behind the deal. Don't make assumptions just based on what the press has written or what the talking heads are saying. There are always conditions on a deal, and there's always the possibility (however remote) that something could happen to torpedo it. I found the details of the tender offer you're referring to. Quote: Terms of the Transaction [...] The transaction is subject to certain closing conditions, including   the valid tender of sufficient shares, which, when added to shares   owned by Men’s Wearhouse and its affiliates, constitute a majority of   the total number of common shares outstanding on a fully-diluted   basis. Any shares not tendered in the offer will be acquired in a   second step merger at the same cash price as in the tender offer. [...] Financing and Approvals [...] The transaction, which is expected to close by the third quarter of   2014, is subject to satisfaction of customary closing conditions,   including expiration or termination of the applicable waiting period   under the Hart-Scott-Rodino Antitrust Act.  Both Men’s Wearhouse and   Jos. A. Bank are working cooperatively with the Federal Trade   Commission to obtain approval of the transaction as soon as possible. [...] Essentially, there remains a small chance that one of these "subject to..." conditions fails and the merger is off. The chance of failure is likely perceived as small because the market price is trading close to the deal price. When the deal vs. market price gap is wider, the market would be less sure about the deal taking place. Note that when you tender your shares, you have not directly sold them when they are taken out of your account. Rather, your shares are being set aside, deposited elsewhere so you can no longer trade them, and later, should the conditions be satisfied, then you will be paid for your shares the deal price. But, should the deal fall apart, you are likely to get your shares deposited back into your account, and by that time their market value may have dropped because the price had been supported by the high likelihood of the transaction being completed. I speculated once on what I thought was a "sure deal": a large and popular Canadian company that was going to be taken private in a leveraged buyout by some large institutional investors with the support of major banks. Then the Global Financial Crisis happened and the banks were let off the hook by a solvency opinion. Read the details here, and here. What looked like a sure thing wasn't. The shares fell considerably when the deal fell apart, and took about four years to get back to the deal price.