| "Tuesday May 16, 7:54 am Eastern Time Company Press Release
 
 Web Street Thanks Clients With First Free Trading Day On the Internet
 
 Thanks Loyal Clients and Celebrates Upcoming Self-Clearing With One Full Day of Commission Free Internet Trades on May 30th
 
 DEERFIELD, Ill.--(BUSINESS WIRE)--May 16, 2000-- Web Street, Inc., parent company of Web Street Securities, Inc., (NASDAQ: WEBS - news), a leading online brokerage firm recently awarded a five star customer service rating in Money Magazine's ``Best Online Brokers of 2000'', today announced its first ever day of free Internet trading for all of its clients. To thank its loyal customers for their business and to celebrate the company's upcoming move to self-clearing, Web Street will be offering its account holders one full day of unlimited, commission free Internet trading on Tuesday May 30th 2000.
 
 Joseph J. Fox, Co-Chief Executive Officer of Web Street, commented, ``With the company riding on the heels of a successful quarter, and with self-clearing and international trading on the way, we are very pleased to announce this free trading day to our customers as a token of our gratitude for their continued business and support. In the online brokerage industry, success is a two-way street. By maintaining strong and responsive relationships with our clients, we are confident in a bright future for both Web Street and our customers.''
 
 The upcoming trading day will give all Web Street customers an unlimited number of commission free Internet trades on May 30th 2000. The free offer applies to both market and limit orders of stock and options trades executed on that day. This free trading day represents a valuable offer to the Company's customers and is yet another in a succession of industry innovations, which includes Web Street's Mutual Fund SuperSite(SM), offering access to over 4,000 commission free mutual funds every day.
 
 Much of Web Street's impressive growth has been driven by an expanding client base, achieved by increased marketing and customer referrals in the United States and abroad. Due to these new clients, all of Web Street's key operating metrics increased significantly in the first fiscal quarter ended March 31, 2000, including total revenues, total customer accounts, total customer assets and total trades executed.
 
 Mr. Fox continued, ``We are very happy to be offering this free trading day to our customers to kick off the exciting events in the coming months. With our new brick and mortar locations in San Francisco, Denver and Boston opening later this summer, and our expanded portfolio of services made possible by self-clearing, Web Street's customers can look forward to a greater range of financial products available through both online and retail channels.''
 
 About Web Street
 
 Web Street, Inc., based in Deerfield, Illinois provides online brokerage services to individual investors in the United States, Europe, Asia and Latin America, through its wholly-owned subsidiary, Web Street Securities, Inc., which was founded in 1996. Web Street has been rated highly in numerous publications, including Money Magazine's ``Best Online Brokers of 2000'', four star ratings by Barron's in 1998 and 1999, and ranking as one of SmartMoney's top three online brokers in 1998 and 1999. Web Street offers 24 hours a day customer service, low-price commissions, and real time account information via multiple channels - online, touch-tone telephone, person-to-person via telephone, and face-to-face onsite through its existing and future brick-and-mortar branches. For more information on the Company's products and services, visit us at www.webstreet.com or call us at 1-800-WEBTRADE.
 
 Cautionary Note Regarding Forward-Looking Statements
 
 This news release includes forward-looking statements that reflect Web Street's current expectations about its future results, performance, prospects and opportunities. Web Street has tried to identify these forward-looking statements by using words such as ``may,'' ``will,'' ``expect,'' ``anticipate,'' ``believe,'' ``intend,'' and ``estimate'' and other similar expressions. These forward-looking statements are based on information currently available to Web Street and are subject to a number of risks, uncertainties and other factors that could cause Web Street's actual results, performance, prospects or opportunities in the remainder of 2000 and beyond to differ materially from those expressed in, or implied by, these forward-looking statements. These risks, uncertainties and other factors include, without limitation, Web Street's ability to establish and maintain international relationships and relationships with content providers, intense price and other competition among companies providing online financial services, Web Street's need to maintain and increase its customer accounts, Web Street's ability to successfully implement self-clearing operations, Web Street's ability to obtain required regulatory approvals for and successfully implement self-clearing operations, volatility in the securities markets, Web Street's ability to develop and enhance its services and products, risk of system failures, and existing and future regulations affecting the online brokerage industry or the Internet generally. For further information about these and other risks, uncertainties and factors, that could affect Web Street's future results, performance, prospects and opportunities, please review the disclosure included under the caption ``Business-Risk Factors'' in Web Street's annual report on Form 10-K for the year ended December 31, 1999, as filed with the Securities and Exchange Commission. Except as required by the federal securities laws, Web Street undertakes no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events, changed circumstances or any other reason after the date of this news release.
 
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 Contact:
 
 Investor Contact:
 Cheryl Schneider/Hulus Alpay
 or
 Press Contact:
 Blake Eastman/Laura Novak
 Morgen-Walke Associates
 212-850-5600"
 
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