Thanks AntSamuel but I didn't say gov agencies but instead I said politicians. Here's one timeline on how the massacre and some of the investigations went down, which might clear things up for you:


A meeting occurred in late October, 1928, in the Chicago Heights area, which was a place that Al Capone often used as a hide out. Capone gathered his men at the house of the new rising boss of the Chicago Heights faction, Vincenzo Ammirato a.k.a. Jim Emery. Other gangsters who attended this meeting were Frank LaPorte, second in command of Emery, Sam Costello, the boss of the Sicilian faction in the Heights, James Summons, a known murderous Capone associate, Louis Campagna, Rocco DeGrazia, and "Circus gang" leaders and associates from the North Side area Claude Maddox and Willie Heeney. There were possibly two agendas at this mob convention, one was the placement of Emery as the new acting boss of the Chicago Heights since the previous boss Dominic Roberto was having deportation problems, and the second agenda was the problem with the Northsiders and how to solve it. These are obviously only speculations because most of the men who attended this so-called Mob meeting, including Heeney, Summons, Maddox and DeGrazia, all were current enforcers and had more muscle than brains. Maybe some of these guys were only there as Capone’s personal security but coincidentally was that all of them were also good logisticians and simply there were too many of them in one place at the same time.


In late November 1928, Capone called for another meeting with the boys from out of town and this particular meeting took place at a house on Cranberry Lake, six miles north of Couderay, Wisconsin. Allegedly present at the meeting besides Capone were Frank Nitto and Louis Campagna, with Fred Burke, Gus Winkler and Fred Goetz on the opposite side of the table. Now for these types of killers and shooters to seat with the top Italian crime brass of Chicago at the time, was almost unthinkable only if there was obviously something important to be further proceeded. So here’s where the political connection comes in, meaning two other individuals who also attended the meeting were the First Ward Republican committeeman and possible Capone member Daniel Serritella and also North Side politician William Pacelli, who in turn was probably brought by Serritella regarding the police protection in his territory, which is a possible answer on why they would bring a North Side politician to this particular meeting?! This organized crime convention lasted for almost two weeks and the men were hunting, fishing while allegedly planning the elimination of the Northsiders and the logistics during the execution, obviously with the help of the so-called “out of town boys” who would all receive a $5,000 payment for the job and the task for the crooked politicians was to take care of the law during and after the hit. Also since he was America’s most famous mobster and was usually blamed for every single crime which occurred in his city, Al Capone decided that it’s better to leave town during the operation and to enjoy his summer home in Miami, Florida, which would also be his main alibi. This testimony comes from Byron Bolton who allegedly also attended the meeting but his role was to serve the big shots with drinks and prepare meals.


Now I believe that the close police connection and the ideas of using police cars and uniforms comes in early December, 1928, when one William Davern Jr was shot and killed by a member of the Moran gang during a fight in one shady hangout at the time which was known as the C&O Cabaret and Restaurant at 509 North Clark St. The biggest problem was that the late Davern was the son of a Chicago police captain and also the cousin of Capone member William “Three-Fingered Jack” White. So I personally believe that both, meaning the police captain and the ruthless gangster, were screaming for blood and were also somehow involved in the logistics of the future assassination. For example that same month, the boys bought a police Cadillac from an auto dealership on Irving Park Road and the car previously belonged to Cook County Commissioner Frank Wilson and the individual that was sent to buy the car identified himself under a different name such as “James Morton (Martin?) from Los Angeles”, which in reality was Byron Bolton. They also bought another car, Peerless Sedan, under the same false name. The plan was for Bob Carey to drive the false police car with Fred Burke and Fred Goetz dressed as cops and another gangster known as Rocco Belcastro would be driving the other car with the other two hit men, Gus Winkler and Ray Nugent, dressed as civilians.


On February 1, 1929, one member of Detroit’s Purple gang called the Northsiders and said that he had the shipment with booze ready and will deliver it on February 14, 1929, Valentine’s Day, between 10 and 11 a.m. They assured the caller that they would be there to help unload the truck in the gang’s garage on 2122 North Clark Street. It was allegedly a betrayal since after that the caller informed the Caponites that there will be a shipment of booze on Valentine’s Day at Northsiders’ hangout on N. Clark St. That’s the same moment when Byron Bolton, one Jimmy Moran and Jimmy McCryssen rented rooms along North Clark Street, across the garage which in fact was a regular hangout for the Northsiders. So Bolton and Jimmy Moran rented a room at 2119 N. Clark St. which was owned by Mrs. Michelle Doody and McCryssen accommodated himself on 2125 N. Clark St. at Mrs. Minnie Arvidson’s apartments. The three men represented themselves as cab drivers who worked the night shift and they insisted on rooms in the front, overlooking Clark Street. The three men rarely left their rooms and for the next ten days they constantly overlooked the area. Their job was allegedly to watch for Bugs Moran and to make a phone call to the Circus Café and to inform the hit squad the same second when Moran and his gang will enter the garage.


The morning on Thursday February 14, 1929, the temperatures were bellow zero and the streets were covered with snow and ice, thus causing a bad rush hour. The first North Side associate that came to the scene at about 8:30 a.m. was John May, then the two Gusenberg brothers, Frank and Pete, arrived at about 9:30 a.m. followed by James Clark, Adam Heyer and Dr. Reinhardt Schwimmer who was only a friend of some of the gang members. The last to enter the garage at 10:30 a.m. was probably Albert Weinshank, the man who very much resembled Bugs Moran and that’s when Byron Bolton from the lookout crew across the garage allegedly made a mistake. He thought that Weinshank was in fact Bugs Moran because from a distance he bore a big resemblance to Moran and so Bolton made the call to the boys at the Circus Café and informed them that their target has arrived. The killers were waiting in their cars in a rented garage at 1722 North Wood St. which was rented under a false name of “Frank Rogers”. With the signal from Bolton the killers headed for the SMC Cartage Company garage and took north along Wood Street for a mile to Webster Avenue, then east for two miles on Webster to Clark, which would have taken about fifteen minutes. The first car with the fake policemen arrived at 10:45 a.m. in front of the garage and the second car left the two killers in civilian clothes at the back of the establishment. The two “cops” entered the garage and their role was to persuade their victims to surrender their weapons without a fight, which was the reason behind the police uniforms. The “cops” rounded up the seven men up against the wall and then one of the “cops” opened the back door and let the other two men enter the garage. The two guys pulled out their two Thompson machine guns and the “cops” pulled out a shotgun and a revolver. Suddenly machine gun rifles were heard all around the neighbourhood and each Moran gang member was riddled with bullets. After the murder, the hit squad then staged their final part of the job and that was to confuse any witnesses as they reappeared on the street. The two hit men, who posed as policemen, took out the other two men as their prisoners, entered the fake police car and sped away. Also the lookout crew vanished at the same time and the killers returned to their previous location and left the fake police car at the rented garage on Wood St. and fled the area.


Eight days later, on February 22, the so-called “cleanup crew” which included Tony Capezio, Joseph Lolordo and Raymond Schulte, needed to get rid of the getaway cars. First they dynamited one of the cars in west suburban Maywood, the area where Claude Maddox and his family lived at the time and than they came back to the garage at 1723 North Wood St., to demolish the second getaway car, the phoney police black Cadillac. They mainly used acetylene torch, axes and hacksaws but Capezio allegedly made a mistake that nearly cost his life. While he was cutting through the gas tank with the acetylene torch, a fire broke out and blew him to the ceiling, while knocking him unconscious. The reason was that he forgot to empty the gas tank and so Capezio burned his arms and hands. His two companions took him to the North Avenue clinic, but when they arrived there they suddenly ran back out because they realized that someone might’ve heard the blast and might be calling the cops. This stunt allegedly earned Capezio’s nickname “Tough Tony.” Several years later bank robber Alvin Karpis, who was a close friend of Capezio's, also confirmed the story. So when the fire broke out in the garage the firemen who answered the call discovered the black Cadillac that had been partially demolished and called the cops. Some of the witnesses said that three men were seen leaving the burning garage after the car exploded and at least one was said to be injured.


The Chicago Association of Commerce immediately posted a reward of $50,000 for the arrest and conviction of the killers. And additionally the angry public collected another $10,000 for the reward. The city council and the state’s attorney’s office each added $20,000, bringing the total to $100,000, the biggest price ever put on the heads of gangsters. The main Capone connection within the investigation started when the cops found out that the man who rented the fake police car under the false name “Frank Rogers” also gave his address as 1859 W. North Avenue, which was a place just few doors behind the infamous Circus Café. That’s when the cops suspected that the Capone gang or the so-called Circus gang, which was a name invented by the newspaper men, had a hand in the bloody situation. They immediately arrested Claude Maddox who was found in his Circus Café and they searched the place and found a Thompson drum full of cartridges and also many overcoats strewn about the back of the joint and they even found a loaded .45 in one of the overcoats. Maddox was brought in the police station for questioning, but he was later released when he showed his alibi by being in court on an unrelated charge at the same time when the massacre occurred. Judge Peter H. Schwaba later confirmed Maddox presence in his court from 9:30 to 12:15 o’clock on the same day of the murders, which took at about 10:45 a.m. The investigation on Maddox didn’t really stopped since later they also found out that Maddox was once implicated in the collecting of a defence fund to pay the bail for three Capone gang associates Harry Burton, Frank Carlson and James O’Brien were arrested in a house near Crystal Lake for the kidnapping of some wealthy automobile dealer and the interesting thing was all three defendants were once suspects in a similar massacre that occurred in Ohio, when three hit men dressed as policemen entered a garage and killed five members of a beer gang. After collecting the so-called defence fund, Maddox obviously managed to sent the cash to the right places since during the trial of the three defendants, Burton was acquitted but the other two guys were sent to 5 years in jail. This action called for an investigation of the jury and one juror was sent to six months in jail for taking a bribe. Two weeks after the release of Burton the massacre of the Northsiders gang occurred, which throws the theory that Burton might’ve been one of the shooters.


The investigation continued with questioning all of the residents in the neighbourhood and the people who lived around the garage where the massacre occurred. When they questioned Mrs. Michelle Doody, she said that there were two guys in her rented apartment on the second floor, who constantly overlooked the street and rarely got out. The cops felt suspicious and decided to check out the apartment. During the search, they found a letter and a prescription bottle with the name of Byron Bolton. They didn’t thought about the significance of this clue until years later. But either way they started a search for Bolton for any possible explanation. But the thing was that by this time the out of town hit squad and Bolton fled the city and they were hiding out from any possible questionings by the police.


On February 26, 1929, Deputy Police Commissioner John Stege issued an order for the arrest of 17 well known criminals in the Chicago area. He believed that some of the men on the arrest list may have been the actual killers and the other might have knowledge about the situation. The first one to be arrested was Rocco Belcastro because his description given by a witness corresponded with the description of a man with a missing finger on his hand that drove the getaway car. Second on the list was Vincenzo Gibaldi a.k.a. Jack McGurn but he had a strong “Blond” alibi. His girlfriend backed his story and the cops found room service orders from the time when the massacre occurred. Again Claude Maddox found himself at the top of the suspect list and was taken for questioning. Maddox was a major hope for the investigation but he disappointed the cops because he kept his mouth shut and they had nothing on him since he again used his court alibi. The cops also arrested Joseph Lolordo because he lived next door to the garage where the demolished car has been found and another Capone member Danny Vallo, it was said, had voluntarily appeared at police headquarters when he previously heard about the arrests and warrants. Others arrested were Willie Heeney, Raymond Schulte, Tony Capezio, Rocco Fanelli, Tony Barone, Frank Diamond and also Bugs Moran and some of his friends and allies, including Sam and Joe Aiello, Rocco Griffo, William Rode, Charles Kakel, Frank Milici and George King. The cops also questioned the Jewish mob boss and Capone’s right hand man Jake Guzik. They had records that Guzik called Capone in Florida from The Congress Hotel shortly before, and after the massacre went down. In the end, no one dared to talk.


During another raid on a roadhouse in Forest Park, which was owned by the Capone gang, the cops also found a police star. The star no. 65 was issued to D. Alzell and it was very strange for the investigators because the killers in the massacre were dressed as policemen with police stars and the uniforms were never to be found. Also on March 5, 1929, the cops raided a liquor depot on the North Side which was operated under the auspices of Claude Maddox and Danny Vallo. During the raid, on the wall of the garage the cops noticed a paper with the names, home addresses, telephone numbers of two police officers and also information where they might be reached in ant hour of the day. But for unknown reasons Police Commissioner John Stege decided to ignore these two cases. My own believe is that these two obviously corrupted cops were the ones who provided the police uniforms and also information about one of the cars that was used in the hit. Since this was a big case and the public was outraged, maybe the Police Commissioner didn’t want any bad reputation for the Chicago police or even possible involvement in the massacre to be uncovered during this period. So he decided to push forward the idea that only paid killers from out of town were involved in the multiple murder case. So an angry group of wealthy Chicagoans decided to put up a large sum of cash for a scientific crime detection laboratory to be installed at Northwestern University. This lab, which was first of its kind, was completed by the end of 1929 and its first case was the St. Valentine’s Day Massacre. So they acquired guns and bullets from the police stations to determine whether the actual shooters were in fact real police officers. But the results came out negative and the forensic ballistics showed that in no instance was found a duplication of markings to indicate that any police weapons had been employed in the killings.


But the investigation really started changing that same time period or when Fred Burke killed a police officer and managed to elude the government for over a year. When the cops raided Burke’s house, they found a bullet-proof vest, two Tommy guns, pistols, and thousands of rounds of ammunition. Ballistics tests proved that both of Burke's Tommy guns had been used in the St. Valentine's Day massacre. The same tests showed that one of them had been used in the murder of gangster Frankie Yale. So now everyone who was allegedly involved in the Saint Valentine’s Day murders became too hot for the syndicate to deal with. The up and coming Chicago criminal administration decided to start a clean up, meaning to get rid of all of these hot heads that didn’t generate high sums of cash and were involved in unsanctioned robberies and hits that also might affect their illegal enterprises. But Burke managed to escape the wrath of the new up and coming gangsters because he was arrested back in 1931 at a farm near Green City, Missouri and was sentenced to life in prison. In October 1931, Fred Burke was visited by Capone’s old bodyguard and trigger man Phil D’Andrea at Marquette prison in Michigan. According to the prison’s Warden James Corgan, D’Andrea simply exchanged just few words with Burke and than left. Obviously D’Andrea’s visit was to make sure that Burke will keep his mouth shut about his previous involvements with the Capone mob or else. After that Burke was never pressed to answer any questions about the St. Valentine’s Day Massacre. In 1931 Nugent disappeared and legend goes that he had become a liability to the Outfit and had been taken out into the Everglades and fed to the alligators. Bob Carey heard about the news so in 1932 he decided to leave town together with his wife and headed to New York. According to police reports, on the night of July 29, 1932, Carey shot his wife to death, after which he turned the gun on himself. Some investigators believe that Carey and his wife were in fact killed by the mob. Fred Goetz also managed to remain as criminal force in Chicago. At first he controlled some of the rackets in Cicero for the Outfit under the auspices of Claude Maddox and Willie Heeney. After a while he wanted to claim independence which was his biggest mistake. Also one of his close associates Verne Miller was accused of helping gun down three policemen and a federal agent in an attempt to free bank robber Frank Nash during the infamous Kansas City Massacre. Story goes that Winkler gave information about the massacre to FBI’s Chicago field office. Goetz forgot about being constantly watched by the new organization and so on March 20, 1933 he was murdered in a drive-by shooting outside of a closed Cicero restaurant, the Minerva. Gangster Alvin Karpis believed that Frank Nitto ordered the murder and Maddox together with Heeney delivered it. Gus Winkler also remained as force for the Chicago Outfit by controlling the rackets on the North Side. And he also tried to gain independence from the Outfit. So on October 9, 1933 Winkler was headed to the beer distribution office of Charles Weber at 1414 North Roscoe Avenue. Upon his arrival Winkler was hit with 72 shotgun pellets by mob assassins. As he lay down in his own pool of blood, Winkler managed to gasp out the Lord’s Prayer before he died. William White's body was found in his Oak Park apartment, suffering gunshot wounds to the head and body, after a gunfight with two unidentified gunmen seen fleeing from the building on the night of January 3, 1934.


On January 8, 1935, FBI agents surrounded a Chicago apartment building at 3920 North Pine Grove, looking for few members of the infamous Barker-Karpis Gang, in connection with the kidnapping of banker Edward Bremer. After a brief shootout which resulted with the death of gangster Russell Gibson Bremer was rescued and the kidnapping gang was arrested. Among those taken into custody was also Byron Bolton. During the questioning, to the agents surprise, Bolton started talking. He pointed out the Barker gang’s main hideout in Florida and among other things he also claimed to have taken part in the infamous St. Valentines Day massacre. According to Bolton the main people involved in the massacre were Burke, Goetz, Winkler, and Nugent. But some of Bolton’s claims didn’t add up because he started throwing names like Maddox, Humphreys and Carey and these guys already had their own alibis. The problem was that most of these fellas were dead or in jail by now. Burke was sent to jail for the rest of his life and Humphreys was serving an 18 month term in Leavenworth prison for income tax evasion. The only suspect who was named in Bolton’s testimony and was still free on the streets of Chicago was again 35 year old Claude Maddox. On January 25, 1935, Maddox was arrested as he walked in his home at 2240 S. Oak Park Avenue, Berwyn and was brought to the police station for questioning again regarding the massacre. But a strange thing happened at the station. No one wanted to question Maddox regarding the slayings. It looked like every cop in the station was afraid of Maddox. The only cop who had the courage to ask him a few questions was Chief Detective John Sullivan. But Maddox didn’t say much except that he was in court during the time of the massacre or in other words he used his old alibi which was very useful. Bolton claimed that Maddox was indeed in court but he paid the corrupt judge to let him sneak for a while at 9 a.m. to accomplish the task with the other killers and than again returned to the court room before noon when his case was called. But Bolton’s testimony on Maddox was very unbelievable and if it was true it was very hard to prove it. Maddox’s court statement was supported by his attorney Tyrell Richardson and also by government officials. So Detective Sullivan had no other choice except to hold Maddox for the night and to release him the next day. The detective told the reporters “So far as I know, Maddox has no connection with the massacre and he’s not wanted here in Chicago for any crime”.


When the cops raided Bolton’s home they found numerous pictures of him together with Al Capone and other gangsters such as Fred Burke and Fred Goetz, which confirmed the Mob conference which occurred back in 1928. A veteran of the police force in Chicago Sergeant Samuel Loftus said that “Every detail that Bolton pointed out is true to my personal knowledge. I lived that case and as a matter of fact I’m still working on it. The Maddox angle is not only possible but I believe that is the answer to the puzzle of his alibi. We know that Maddox was involved but couldn’t prove it”. While leaving the police station Maddox allegedly said to his attorney “Well that’s one rap they can’t hang on me”. The shady director of the Federal Bureau of Investigation J. Edgar Hoover immediately dismissed Bolton’s testimony by saying “There’s not a word of truth in it” but the agent in charge of Chicago’s Division of Investigation D. M. Ladd said that “The Federal Agents haven’t even questioned Bolton regarding the massacre”. The only gangster that wasn’t mentioned in Bolton’s testimony, but was believed by every cop in Chicago that he had some involvement in the massacre, was Jack McGurn. The strange thing was that in 1936 the evening before Saint Valentine’s Day, or in other words the Massacre’s seventh anniversary, McGurn was killed by his peers while bowling and celebrating and that’s why I believe that McGurn’s demise on the same day when the massacre occurred 7 years ago wasn’t a coincidence, but it was a straight message from the boys. And that’s how it all ended.