Brian Cashman has made some gutsy trades in his time with the New York Yankees, but nothing compares to his latest stunt for the holidays.

New York Yankees General Manager Brian Cashman has sat through endless winter meetings in his career, so it is no surprise that he is seeking a little excitement during this off-season.

Cashman spent Friday morning rappelling down the 22-story Landmark Square building in Stamford, CT with plenty of press on hand to witness the event.

As you can see in the video, Cashman delivers no hesitation when it comes to making the drop down the building. Maybe that’s why he’s such a stone-cold negotiator for the New York Yankees; he simply has no fear.

Cashman’s daredevil act is one that has done several times. In fact, this practice is in anticipation of Stamford’s annual “Heights and Lights” event that will take place on Sunday. This will be his seventh year participating in the event, according to the New York Daily News.

His practice prepares him for Sunday’s event, where he will rappel down the building in costume along with Santa Claus and a varied cast of Christmas characters.

The event is a family-friendly celebration of the Christmas holiday, which will also include live music and the annual lighting of the town’s Christmas tree, according to Stamford’s town website.

Cashman’s bold move left people in awe at just how daring this mild-mannered GM is. Hopefully, his daring act out of the office points towards gutsy moves coming up this off-season for the Yankees.