Paul Toboni laughs when he thinks about it now. As a young professional looking to break into the baseball business out of graduate school, he reached out to then-Red Sox general manager Ben Cherington in 2015 to apply for one of the club’s front office internships.

A former Division 1 player at the University of California who’d already interned for a few months with the Oakland Athletics, Toboni’s qualifications were strong but he didn’t feel like a slam dunk. Yet he got the job, and upon joining the organization he learned he’d come highly recommended by Cherington himself.

At least that’s what the hiring managers believed, after Cherington forwarded them his resume.

“I think by Ben forwarding the email I sent to him they kind of took it as an endorsement from Ben when I’m not sure it was,” Toboni said. “I think luck was on my side there.”

Lucky or not, Toboni made the most of his big opportunity and has quickly risen through the ranks in the Red Sox front office. Within a few years he’d become an integral part of the club’s scouting operation and by age 30 he was overseeing the entire draft. Thanks in part to his efforts and the talent he helped identify, the Red Sox now boast one of the best farm systems in baseball and this past offseason he even earned an interview for Boston’s vacant head of baseball operations job.

That position wound up going to Craig Breslow, but after only a few weeks working together he decided to promote Toboni to assistant general manager, cementing the 33-year-old’s status as a rising star in the front office world.

“He thought it made the group better, and I was obviously extremely grateful,” Toboni said of the promotion, which made him one of four assistant GMs in the front office. “It’s one of the areas where I’m maybe most grateful having worked with the Red Sox, I’ve worked with some really cool people that I’ve learned a tremendous amount from. Honestly thinking back, Ben was here, Dave (Dombrowski) when he was here, Chaim (Bloom) and (Brian O’Halloran), of course, and Bres in a short period of time, I’ve learned a lot from all these people.”

Originally from San Francisco, Toboni grew up steeped in the Bay Area sports scene at a time when it was entering a golden era. As he entered young adulthood, the San Francisco Giants were on the verge of winning three World Series titles in five seasons, the Golden State Warriors were laying the foundation of their eventual dynasty and the San Francisco 49ers had turned the corner and re-emerged as Super Bowl contenders.

“That community is very important to me,” Toboni said, noting his excitement for next weekend’s Super Bowl. “I’m one of five and my folks and my siblings, but also the greater community, they did a tremendous job in my opinion of showering kids with love but also holding really high expectations for how you should carry yourself and how you should go about your work.”

During that time Toboni also starred on the baseball diamond and earned the opportunity to play at Cal alongside future big leaguers like Marcus Semien and Mark Canha, but a series of hip surgeries limited him to just 25 games over four years. Upon graduating in 2012 he decided to pursue an MBA from Notre Dame, but after initially thinking he might want to get into finance or consulting, he eventually felt the pull back to baseball.

“One of the trainers that rehabbed two of my hip surgeries was working for the Oakland A’s, so I reached out to him asking if there were any internships available. There was, I interviewed for it and I got it,” Toboni said. “So I did a three-month internship there, then I went back to graduate school and when I was in my second year there I interviewed for more internship opportunities, at which point the Red Sox offered an internship, and I took it.”

After 10 months as an intern Toboni earned a full-time job with the Red Sox as an area scout, and roughly a year later he was promoted to assistant director of amateur scouting. Towards the end of the 2019 season he was promoted again to director, and in that role he led the drafts that brought top prospects like Marcelo Mayer, Roman Anthony and Nick Yorke into the organization.

Last year Toboni was elevated again to vice president of amateur scouting and player development before receiving his current title as senior vice president and assistant general manager. Toboni said his focus will remain primarily on amateur scouting and that his responsibilities won’t significantly change, but that he’ll now be more involved with the major league team and how it’s being run.

“It’s not to say I wasn’t before, Chaim was great with that and very inclusive as it relates to all this, but I think formally it’s acknowledged in a way that it wasn’t before,” Toboni said.

Arguably Toboni’s biggest contribution to the Red Sox so far has been his involvement in bringing aboard Mayer and Anthony. Along with last year’s first-round pick Kyle Teel, they are now viewed as foundational pillars of the next great Red Sox team, and this winter the club’s top decision-makers haven’t been shy about saying so.

Though they’re still only in Double-A, the emerging core of prospects have so far become everything the Red Sox could have hoped for, and Toboni said he’s taken a lot of pride and joy in watching them develop.

“It’s been super fun to watch their trajectories on the field,” said Toboni, who lives in Charlestown and is a father of three young kids. “I’ll tell you what’s far more gratifying though is just being around all of them. Seeing, one, their love for the game, but two, their love for each other and the way they go about conducting themselves. They’re incredibly mature for the ages they are, and from my vantage point they go about their work the right way.”

Toboni’s time leading the Red Sox scouting department has also been marked by a heavy emphasis on position players, particularly middle infielders. The club has invested significant draft resources shoring up that area over the past four years, and as a result the organization is now brimming with talent up the middle.

But with Breslow now leading baseball operations and the club’s renewed emphasis on pitching development, is it possible we might see a change in the way Boston conducts its drafts?

“It’s surely a possibility,” Toboni said. “The bottom line is we’re in a different position now than we were three years ago, which is a different position than we were last year. Not only is the makeup of our farm system different but our concentration of talent is closer to the major leagues. That all informs how we’re going to go about valuing prospects.”

Top Red Sox prospect Roman Anthony makes a throw while playing for the Greenville Drive. (Kelly O’Connor photo)

No matter what path the Red Sox front office charts in the months and years ahead, it looks as if Toboni’s place in Boston is secure. He’s survived three changes in baseball leadership in less than a decade, quickly earned the backing of his newest boss, and if the Red Sox emerge as contenders in the coming years his fingerprints will be all over the roster.

Whether through hard work, talent, luck, or a combination of all three, Toboni says he’s grateful to have walked this path and that it wouldn’t have been possible without all the people he’s worked with along the way.

“Whether it was my time as a scout, or when I came back to the front office I’ve been exposed to some awesome people and I’m fortunate to have been able to learn from them,” Toboni said. “At different parts along the way I’ve found ways to hopefully contribute to the group and it’s recognized in my title, but more importantly it’s become part of what I’ve done as part of this larger group working towards this shared goal and vision.”

O’s sale bad news

This past week news broke that the Baltimore Orioles are being sold, and that in the coming years the Angelos family will hand over control to a group led by hedge fund billionaire David Rubenstein for $1.7 billion. Rubenstein’s group will initially buy a 40% stake in the club and will assume control of the rest following the death of 94-year-old Angelos family patriarch Peter Angelos.

The news was greeted with widespread jubilation among Orioles fans, but it should also send a chill down the spine of everyone else in the AL East.

Over the past two decades the Orioles’ payroll has consistently ranked in the bottom half of the league, and since John Angelos took over for his father as control person in 2018, the club has slashed salaries to the bone. Baltimore has consistently ranked last or bottom three in payroll while undergoing an aggressive rebuild, and this past season the Orioles boasted an Opening Day payroll of just $60.7 million, ahead of only the moribund Oakland Athletics.

Yet thanks to the smorgasbord of young talent they’ve amassed, the Orioles still won 101 games. Imagine what they could do if they start spending too?

With deep-pocketed owners, the Orioles could triple their previous payroll and still only rank near the league average. The first order of business would no doubt be to sign homegrown stars like Adley Rutschman and Gunnar Henderson to long-term extensions, ensuring they remain in Baltimore much like the Atlanta Braves have locked up their own core.

Milwaukee Brewers starter Corbin Burnes adjusts his hair as he pitches against the Pittsburgh Pirates during the first inning of a game on Tuesday, Aug. 2, 2022 in Pittsburgh. He’s now a member of the Orioles. (AP Photo/Keith Srakocic)

Then, the Orioles could make like the Los Angeles Dodgers and start splurging in free agency, signing multiple top starting pitchers and shoring up any conceivable weakness they might still have. They just traded for Brewers ace Corbin Burnes, and while before the idea of Baltimore signing an ace like him to a long-term deal would have been inconceivable, now it’s a real possibility he could pitch in Baltimore the rest of his career.

Baltimore was already going to be a problem for the rest of the division as it is, and now with money to spend they could potentially emerge as a powerhouse for the rest of the decade and beyond. That’s bad news for Boston, because even when the Red Sox do get back off the mat, they aren’t going to have the Orioles to kick around like they could for most of the 21st century.

Pelham native climbing

This past Thursday the Red Sox announced their minor league coaching staffs, and among the numerous moves and changes that were made official, one local resident earned himself a big promotion.

Juan Rivera, a Pelham, N.H., native who previously served as an assistant coach at St. John’s Prep, has been elevated to pitching coach for the Low-A Salem Red Sox. Rivera spent the last two years as a development coach with Salem, a job that encompassed both analytics and on-field coaching to help young prospects take the next step as players.

Rivera’s elevation was one of numerous changes to the organization’s pitching infrastructure, with the most notable being the hiring of Justin Willard as Director of Pitching. In addition, Dan DeLucia has been hired as Triple-A pitching coach and Shawn Haviland, previously Director of Pitching Development, has been named Special Assistant, Player Development.

Among the notable new hires to the Red Sox system: Former New York Yankees hitting coach Dillon Lawson will serve as Hitting Coordinator with a focus on the upper minors, former Old Dominion assistant Nick Murray will serve as Minor League Rehab Pitching Coach, former Houston Astros head of strength and conditioning Nick Shedd will become Minor League Strength and Conditioning Coordinator, and Driveline Baseball’s JP Fasone will join the organization as High-A Greenville’s hitting coach.