Because prior to the 2013/14 season the Flyers offered Cleary a 3 year deal. Cleary turned it down for a 1 year deal with the Wings on a handshake agreement that he would get a deal in each of the next two off seasons (equaling the Flyers 3 year deal). Holland is simply keeping his word which he should. Signing Cleary now is not a mistake, if anything the handshake deal was the mistake.
Philly denies ever having offered any contract, only a tryout. The only ones talking about the rumored 3-year Philly deal are Cleary and Holland. Also, how is the "handshake deal" and "promise to take care of" Cleary allowed under the CBA? Teams are not allowed to discuss multiple one-year deals. Could be considered cap circumvention.
Besides, it's plainly obvious to everyone except Cleary and Holland that Cleary is DONE, and has been for 3 years.
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