Santiago is wearing 2 citation bars that are not issued by the NYPD. Also, NYPD regulations require that the American Flag bar be worn as the highest citation bar - something Santiago would have known.
Holt wears his Commendation breast bar above his World Trade Center Breast Bar. When the WTC bar is worn, it is worn above all other medals, but below the American Flag bar.
There's a piece of Hitchcock's first gay divorce cake visible on the bar during his second divorce party.
Holt tells Terry that the only muscle he wants to work out is his brain. The brain is not a muscle. Someone as intelligent as Holt would know that.
Holt compares walking his beat to being Sisyphus, "condemned to push the same boulder up the same hill, day in and day out." Sisyphus only pushed the same boulder up the same hill during the day. It was during the night, while Sisyphus rested, that the boulder rolled back down the hill, requiring him to restart his task each day.