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Two men face multiple felony charges after prosecutors allege they robbed an off-duty police officer at gunpoint in Dublin and fled into Oakland before ultimately being caught last Friday in yet another armed Rolex watch theft reported in the Bay Area this summer.

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Raymond Barbosa and Daryl Caldwell were ultimately arrested after crashing their car into a utility box and trying unsuccessfully to run away in the area of Stanley and 98th avenues in Oakland, according to Dublin police.

“The victim’s Rolex watch was recovered along with a handgun believed to have been used in commission of the crime,” Lt. Jared Hattaway told the Weekly.

The Alameda County District Attorney’s Office charged Barbosa, a 21-year-old Oakland resident, and Daryl Caldwell, 23, of Antioch on Monday with second-degree robbery among several felonies and special allegations among the pair.

It was not immediately clear whether the defendants were represented by an attorney, or if they had yet entered a plea to the charges against them.

The situation began unfolding around 12:30 p.m. Friday in the Hacienda Crossings Shopping Center on Dublin Boulevard. An off-duty police officer — whose agency was not revealed — reported having just been robbed at gunpoint outside of the Baron’s Jewelers, according to Dublin police.

The off-duty officer told police investigators that an armed assailant stole his Rolex watch and jumped into the passenger seat of a newer-model Kia Optima that drove away at a high rate of speed, according to probable cause declaration written by Dublin police Officer Thomas Nelson.

The victim provided a detailed description of the robber, saying he was “a Hispanic male adult, approximately 6-foot-3, with an athletic build, holding a black semi-automatic handgun, wearing a black ski mask and all black clothing,” according to Nelson.

The Kia sedan was later spotted on Interstate 580 and Alameda County sheriff’s deputies pursued the vehicle after the driver initially failed to yield. The car got off the freeway but crashed into a utility box on 98th Avenue in Oakland, rendering it inoperable and leading to the two occupants fleeing on foot, according to Nelson.

The passenger — later identified as Barbosa — was allegedly seen by witnesses holding a handgun as he ran. Deputies caught him on Stearns Avenue without further incident and a handgun and ski mask were found in bushes near where he was detained, according to Nelson.

The victim subsequently confirmed Barbosa was the robber during a field identification, Nelson said.

Caldwell — identified as the driver — was detained on Stanley Avenue and had a black ski mask in his possession at the time, according to Nelson. “While on scene, Caldwell spontaneously admitted to driving the Kia and he did not stop due fearing the police,” Nelson said.

Both men were charged with felony counts of second-degree robbery and assault with a semiautomatic firearm.

Barbosa also faces felony charges of carrying a concealed weapon in a vehicle and having a loaded gun on his person in a city, as well as special allegations including personal use of a firearm, having a loaded concealed gun and having an unregistered loaded gun.

Prosecutors additionally charged Caldwell with a felony count of evading police as well as special allegations of weapon use and having two prior felony convictions — grand theft cases in Contra Costa County in 2019 and Alameda County in 2020, respectively.

The Dublin case was the latest in a series of Rolex watch thefts at gunpoint reported in the Bay Area in recent months, including a pair of high-profile incidents in Danville in July and earlier this month.


Jeremy Walsh is the editorial director of Embarcadero Media Foundation's East Bay Division, including the Pleasanton Weekly, LivermoreVine.com and DanvilleSanRamon.com. He joined the organization in late...

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28 Comments

  1. Thug life.

    I wonder where the anti-cop crowd is? Not a word from them in defense of thug life.

    Let’s see, we’ve got three people dead in yesterday’s shooting in Oakland. Then we had a shooting on a BART train. Lots of violence going around in these parts, folks.

    This violence will continue until we enact legislation that will put thug life behind bars for a very long time. The thug life are an opportunistic bunch of cowards run amok. But Malcolm is here to provide a remedy.

    1. First offense: Use of a gun in the commission of a crime, without discharging – 5 years state prison.No good time.

    2. Second offense: Use of a gun in the commission of a crime, without discharging – 10 years state prison.No good time.

    3. Third offense: Use of a gun in the commission of a crime, without discharging – 30 years state prison.No good time.

    4. Use of a gun in the commission of a crime, where suspect discharged weapon at victim – 30 years state prison.No good time.

    5. Use of a gun in the commission of a crime resulting in death of victim, life in prison and no parole. However, should the suspect have a lengthy history of violence, the death penalty should be enforced, and thug life get on chance to appeal.

    Thug life are not the best educated folk out there, but they have the ability to understand that their actions come with consequences when the law is enforced.

  2. @Malcom Hex

    (1) If a crime is committed without the use of a gun, is probation adequate punishment?

    (2) Why are Rolex watches in such demand among inner city thieves? Are they being stolen for resale or for personal use/wear?

  3. The officer must be from an affluent community that pays well.

    Most of the law enforcement officers I have encountered wear Casio G-Force watches.

    @Malcom Hex

    In your case/scenarios (1 through 3), if the gun used is not an actual firearm (and incapable of being discharged), would a stark warning or citation be suitable punishment?

  4. What is the allure of Rolex watches?

    Is it based on some sort of pseudo prestige pecking order as there is with certain car brands (i.e. Mercedes, BMW etc.)?

    I wear a Swiss-made Audemars Piguet which is 10 times more costly than any Rolex and I have never been accosted by street ‘thugs’.

    And like Johnny Cash sings, “I’ve been everywhere, man” including inner city ghettos, barrios, and high-end shopping centers/restaurants.

    I suspect that high visibility and brand recognition contributes to these crimes.

  5. @ Gary,

    My answer to your question #1 is this:

    Just about anything can be used as a weapon; such as a knife, baseball bat, hammer, etc. The difference is that the assailant has to be up close an personal when using those types objects. Having said that, a weapon of any kind used in the commission of a crime that results in a homicide should be treated the same.

    My answer to your question #2 is this:

    You answered your own question.

    @Teresa

    You stated the following: “if the gun used is not an actual firearm (and incapable of being discharged), would a stark warning or citation be suitable punishment?”

    Answer NO. And here’s why: Robbery has to have at least one of two elements to make it a crime, force or fear. If thug life sticks a gun in my face and demands money, I’m going to assume his gun is real. As a result, the fact that I fear for my life constitutes the action by the suspect as robbery – which of course is a felony. I would mention the second element, but I think you get the picture.

  6. @Teresa Klein
    If one uses a toy gun (or even a squirt gun) and tries to rob a bank, when/if apprehended, they will be arrested for attempted or armed robbery regardless of the weapon in question.

    Malcom Hex defined the elements. Even an index finger in concealed in an overcoat pocket can be construed as a weapon if used during the course of a robbery. Intent is another element.

    As for the Rolexes, some consumer goods are considered desirable/luxury items and are coveted by both victims of robberies and thieves alike…one of the reasons jewelry stores, Apple stores, and high-end boutiques are often targeted.

    This in itself is a sad commentary on a society that places far too much emphasis on superficial appearances.

  7. > 5-10-30 years state prison
    @Malcom Hex
    In Connecticut (along with a few other states), imprisoned convicts are charged $269.00 per day for room & board during their incarceration.

    The concept is called ‘pay to stay’ by prison officials.

    This measure was designed to relieve state taxpayers from supporting the full costs of prison incarcerations.

    Depending upon sentence length, some prisoners upon release can end-up owing the state anywhere from $50,000.00 and upwards.

    Prisoner rights activists in Connecticut are trying to repeal this law as it leaves many former convicts with an extensive reparations billing that can often lead to foreclosures, attached wages, and homelessness.

    Question…is this repayment concept draconian and does it only lead to more crime in the long run?

  8. @Malcom Hex
    Should minors (18 and under) committing various examples of the crimes you listed be tried as juveniles or adults?

    And should the sentencing guidelines be less because they are younger and more impressionable than most adults?

    Emotional and mental maturity factors also need to be considered as adolescents are not fully developed in these capacities oftentimes resulting in reckless and irresponsible behavior.

    Can convicted youthful offenders be detoured from a further life of crime by cutting them some slack?

  9. In the case of ‘pay to stay’ incarceration, when the penal system makes it even more difficult for released convicts to assimilate back into mainstream society, crime will continue and everyone pays in the long run.

    As for juvenile offenders of a certain age, they should be offered the choice of incarceration or joining the U.S. military.

  10. @Neil

    Vermont’s repayment concept regarding state prisoners was not just intended to relieve tax payers of the burden of incarcerating inmates, it was also intended to pursued inmates from coming back to prison. Whether or not this concept works isn’t an issue as far as I’m concerned, and here’s why. I’ll use California as an example.

    The recidivism rate among California’s prison population is over 60%. It’s a revolving door. Now, who’s fault is that? Are you going to blame society for the numerous felonies a prison inmate commits? If you do, then you have the same mindset of a career criminal. In other words, it’s always the fault of the other guy, right? Look, prison inmates are people who are opportunistic in the criminal sense. They prey on others people. And by the way, I’m talking about felons who commit violent crimes (rape, murder, robbery, arson, pedophilia, etc). As far as I’m concerned, if you commit a violent crime where death or disablement occurs to the victim, one of two things should happen: life imprisonment or death.

    @Janine

    Let me ask you a question: at the age of, let’s say 16, did you understand what the word murder meant? I did. Now, I didn’t know the elements of murder at that age, but I knew it was very serious and wrong. And please don’t factor in lack of maturity as an alibi for 16 year olds that commit violent crime. Some people are violent. Period.

    @Taylor

    Ah, so now it’s the fault of the penal system as to why violent criminals can’t assimilate back into society? Finger point much, do you? Not the fault of the violent criminal, huh? Well, I don’t feel sorry for people who commit violent crime. I don’t feel sorry for criminals who abuse children. Evil is evil.

    Juveniles of a certain age? Juveniles can’t join the U.S armed services. Furthermore, federal law bars people from enlisting if they have been convicted of any felony. .

  11. “The recidivism rate among California’s prison population is over 60%. It’s a revolving door. Now, who’s fault is that?”

    It is the system’s fault because modern day prisons are supposedly designed to rehabilitate criminals rather than create repeat offenders. The loss of dignity in prisons and abusive treatment by the guards often prompts released inmates to walk out with a chip on their shoulder.

    Improved vocational training is also needed. Instead of training inmates to be cooks and laundry workers upon release, other far more attractive professional options should be made readily available and certain inmates convicted of non-violent crimes (i.e burglary, embezzlement, fraud, etc.) should be allowed to attend courses at local junior colleges and universities to fulfill their academic ambitions.

    If military service is an option for certain inmates, all criminal records of earlier non-violent arrests and convictions should be expunged.

    Starting off with a clean slate can decrease crime providing there are other professional avenues made available.

  12. > certain inmates convicted of non-violent crimes (i.e burglary, embezzlement, fraud, etc.) should be allowed to attend courses at local junior colleges and universities to fulfill their academic ambitions.

    ^ We do not need any more lawyers.

  13. When I was 19, I got busted and convicted for Grand Theft Auto (joyriding). It involved a green ’61 Buick Wildcat convertible in a used car lot that had the keys left in the ignition after hours.

    The superior court judge (Criminal Division) gave me choice of incarceration in state prison or voluntary military service. There were no diversion programs back in the day.

    Long story short, I enlisted in the Navy where I served as a Corpsman in Viet Nam and upon honorable discharge, I used the GI Bill to attend JC and then transferred to UCB where I majored in Human Biology.

    Today I am a retired Physician’s Assistant and had I not stolen that car, things might have turned out differently.

    @Malcom Hex…I believe that violent repeat offenders should be put away for life as their bad genes aren’t going anywhere productive.

    On the other hand, all non-violent offenders deserve a second chance as their energies are simply being diverted towards counterproductive ends.

  14. Let’s take Jerry’s comments by the numbers.

    Point 1: Jerry stated the following: “It is the system’s fault because modern day prisons are supposedly designed to rehabilitate criminals rather than create repeat offenders.” Uh Jerry, what modern day prisons here in the United States are you referring to? Are you talking about new prisons in California? Hope not, because Gavin Newsom’s new budget proposal suggests California could close three more prisons in the next three years.

    Point 2: Jerry stated the following: “The loss of dignity in prisons and abusive treatment by the guards often prompts released inmates to walk out with a chip on their shoulder.” And you know this how? After all, by your reasoning, if an inmate gets his feelings hurt in prison, that makes the inmate commit more crimes? Once again, you blame the system, but not the inmate. Interesting, I’m starting to see a pattern here.

    Point 3: The military is not an option for prison inmates because they are all convicted felons. The United States military does not take convicted felons. Period.

  15. Taking both Mr. Steinburg’s and Malcom Hex’s points into consideration…

    Yes, it is the responsibility of the prison system to rehabilitate its prisoners but the desire to reform has to come from within.

    Yes, prison guards are oftentimes abusive because they are in the position to do so and in many instances, they have psychological issues and demons of their own to contend with. No different than some rogue police officers.

    Very few individuals would actively seek employment as a corrections officer in a prison and therein lies the problem…the applicant pool is very limited with flawed candidates.

    Both inmates and prison guards should consider becoming active members of the prison ministries program, sharing an opportunity to pray together and to seek salvation from a higher authority.

    When prison guards and inmates come to the realization that they are all in the same boat, only then will we begin to see a healing process and ideally, an overall reduction in street crime.

  16. “Gavin Newsom’s new budget proposal suggests California could close three more prisons in the next three years.”

    @Malcom Hex….will the prisoners be transferred to other corrections facilities in CA?

    Another consideration might be to ‘farm out’ inmates to other remote prisons in the United States.

    Nevada and Oklahoma could provide ideal sites as would the Territory of Puerto Rico.

  17. Kyle Ryan stated the following:

    “Both inmates and prison guards should consider becoming active members of the prison ministries program, sharing an opportunity to pray together and to seek salvation from a higher authority.”

    What if the correctional officer and inmate don’t believe in God? Are you going to force them to pray together? Better yet, Jews, Christians, and Muslims are quite different from one another in the spiritual sense. Furthermore, prison ministries is where inmates seek out religion, not from correctional officers. C’mon man, you truly must have posted your piece in jest. Having a little fun with sexy Hexy, are we? That’s okay, a sense of humor is a good thing. But let’s get back to reality.

    The role of a correctional officer is to maintain order, enforce rules, and laws in a state prison. Second, correctional officers are not not counselors, therapists, or doctors. Personal relationships between inmates and correctional officers is strictly forbidden. Do a little research on the role on the role of a correctional officer at CDCR – California Department of Corrections, because you have absolutely no idea what you’re talking about..

    Correctional officers and inmates are not in “the same boat.” Inmates in state prison are convicted felons, who are incarcerated there because they broke the law. Your utopian concept about how both guard and inmate can reach communal bliss is one of the silliest things I have ever heard.

  18. • The military is not an option for prison inmates because they are all convicted felons. The United States military does not take convicted felons. Period.

    Well they should. Though it was just a movie, remember The Dirty Dozen?

    While imposing discipline could pose a problem, why not pardon certain convicts and allow them to fight America’s overseas battles?

    Instead of being outcasts, inmates could become heroes.

  19. Jayson Layne…the U.S. military is actively turning to drone warfare rather than relying on ‘boots on the ground’ and further risking American lives.

    I imagine prison inmates (providing they had the aptitude and general interest), could learn how to operate drones for military purposes but they would first have to be cleared for active military duty by an Executive Order.

    One drone-assisted weapon of interest…

    The ‘Ginzu Knife’ (Hellfire) missile is a non-explosive weapon launched from drones on specific targets to avoid broad collateral damages in civilian areas.

    It is comprised of rotating razor sharp blades that can chop down a two story building and was used to take out 9/11 mastermind Al Zwahiri last month in Afghanistan.

  20. Malcom Hex…you brought up some valid points regarding prison guards but there is room for improvement on their part.

    All correction officers should be college graduates with advanced coursework in psychology and social welfare as this type of education would make them better suited towards dealing with a diverse inmate population.

    The success of a rehabilitation program requires both compassion and an understanding of inmate backgrounds to fully assist them in successfully transitioning into mainstream society if/when their release is granted.

    Simply having a high school diploma or a two-year degree in Criminal Justice from a JC is inadequate.

    A master’s degree should be a prerequisite for either a police officer or a prison guard.

  21. @Malcom Hex

    It is a shame that so many incarcerated individuals return to a life of crime upon release.

    You mentioned that there is currently a CA bill to close down three state prisons and this measure could prove problematic if some convicts are granted early release or cannot be housed elsewhere.

    One option might be to create a number of small towns, preferably in remote rural areas where inmates can experience a living environment similar to life in the outside world.

    Prison guards would be assigned the tasks of the local PD and to emphasize the importance of democracy and freedom, the inmates could be given an opportunity to create and elect their own form of local government to oversee daily matters and concerns and to prevent various malfeasances, it would be more along the lines of a parole board approved steering committee.

    Establishing a variety of jobs and small businesses within this encased community would also generate income and stimulate its own individualized economy.

    To effectively rehab certain convicts requires some latitude and a firm belief that that they can be reformed.

  22. “Instead of being outcasts, inmates could become heroes.”

    @Jason Layne

    We are all inmates to a certain extent perpetually bound by the expectations of a demanding and oftentimes superficial society.

    Some folks are outcasts and true heroes are relatively few these days.

    The question is…do you want to be a prisoner or a guard?

  23. * Do a little research on the role on the role of a correctional officer at CDCR – California Department of Corrections…

    @Malcom Hex…
    I would imagine that correctional officers serving at state prisons are a cut above their counterparts performing similar duties at a county jail.

    Most county jail officers are just one step above a security guard at a shopping mall and seem to enjoy their false sense of empowerment.

  24. @ Malcom Hex/Ray Kendall

    CA state and county correction officer capabilities and skill sets aside, most convicts prefer state prison over county jail because the food is considerably better and various ‘affiliations’ can be renewed along with easier access to contraband.

    And unlike many county jails where inmates are housed in barracks, in CA state prisons inmates are issued a private cell which affords one more privacy and personal space.

    As they say in Motel 6 advertisements, “We’ll leave the light on.”

  25. @Ray,

    Ray said he thinks that correctional officers serving at state prisons are a cut above their counterparts performing similar duties at a county jail. Is that so?

    A Basic Police Academy in California is 24 weeks in length, for a total of 942 hours of training. The schedule may change slightly during some weeks to accommodate training needs (range, emergency driving course, etc.).

    The Basic Correctional Officer Academy in California provides 13 weeks of training for correctional officer cadets in preparation for employment at adult prisons throughout the State of California.

    Lots of law enforcement jobs out there, Ray. Think you can make the grade?

  26. @Ron,

    Most county jails in California house inmates in direct supervision environments based on their security level. You are correct about the fact that most state prison inmates prefer prison to county jails.

  27. “Most county jails in California house inmates in direct supervision environments based on their security level. ”

    ^ Malcom Hex is correct and perhaps speaking from prior experience as a corrections officer.

    There are three main categories or ‘levels’ housed at the county jail…the general population, violent offenders, and the mentally unstable.

    Each group is housed separately and are often assigned different colored jail attire
    for quick identification.

    The general population category is very broad in terms of inmate crimes committed and kept separate from the truly violent and/or mentally-ill inmates in different units.

    The three groups of inmates are often kept separate during bus transfers to criminal court hearings (but not always) as all inmates are waist-chained and handcuffed during the ride to court.

    County jail is usually a holding facility for those awaiting the final outcome of arraignment, pre-trial, trial, and sentencing hearings and if convicted, inmates receive credit for time served prior to the final outcome of their cases.

    County jail is also used to house inmates convicted of lesser crimes and misdemeanors with shorter sentences (one month to a year).

    I am speaking from personal experience having been arrested on a bench warrant for a failure to appear traffic violation.

    Though I was wrongfully arrested, there is usually no recourse in these situations as the police and court officials are granted ‘qualified immunity’ even if their actions are attributable to clerical errors and/or oversights.

  28. “Lots of law enforcement jobs out there…Think you can make the grade?”

    @Malcom Hex…

    Making the ‘grade’ is immaterial to most people because the pay grade for a typical CA county correctional officer is nothing to write home about…around $3,300.00 a month to start and then upwards to about $80,000.00 per year.

    There are better paying jobs out there which might explain the inherent limitations of the hiring pool for this particular occupation.

    County road workers and heavy equipment operators make far more than a county corrections officer as do most county administrative positions.

    And let’s not even get into the private sector.

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