Alex Hassan tried giving up on baseball. It lasted seven months.
The Milton native and former Boston College High School star was drafted by the Red Sox in 2009 and played professionally through 2016, bouncing to the Blue Jays, Rangers, Athletics, and Dodgers along the way.
He appeared in three major league games for the Sox in 2014, making his debut at Fenway Park in the same lineup as Dustin Pedroia and David Ortiz on June 1.
Hassan singled off Erik Bedard in the fourth inning and came around to score on Brock Holt’s double.
“One of the greatest days of my life,” Hassan said. “I have the ball from my first hit and the lineup card.”
Later that season, he pinch hit for Ortiz after Big Papi was 4 for 4 with a home run.
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“He hit four of the loudest balls I’ve ever seen hit and then they sent me up there and I grounded out,” Hassan said.
It proved to be his last major league game. There are no regrets.
“I made it to the majors, and it was such a good experience with the Sox,” Hassan said. “I was able to see how Terry Francona managed when I was called up for games in spring training, and I was around a lot of special players.”
Hassan tried to make it back, but after two seasons with four other organizations in Triple A, he decided it was time to go in another direction.
“The writing was on the wall,” Hassan said. “It was clear my playing career was winding down. My Triple A manager with the Dodgers, Bill Haselman, was encouraging me to potentially pursue a career in baseball.
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“He would talk to me about his lineup decisions and how he handled certain situations. I learned a lot being around him.”
Another former Red Sox player, Gabe Kapler, was with the Dodgers as director of player development. Hassan also got to know assistant farm director Jeremy Zoll.
Those connections led to a six-month internship with the Dodgers front office in 2017 while he was completing his degree from Duke.
“It was a stroke of luck,” Hassan said. “I knew what playing was like and I was able to see it from the other side. It was an immersive experience.”
But once the internship was over, it was time to step away from baseball and come home.
With their first child on the way, Hassan and his wife, Carolyn, decided to settle down in West Roxbury. He put his new degree to use and entered Dell’s sales and marketing training program.
“It’s what made sense for our family,” Hassan said. “Dell was a good company with good people. It was a great experience. I learned a lot.”
But baseball hadn’t given up on Hassan.
Zoll took a job with the Twins as director of minor league operations in 2018. He offered Hassan a position as his assistant.
Had the Twins viewed Hassan as a better fit coaching one of their minor league teams, he likely would have stayed in the corporate world.
But a front-office position intrigued him and Hassan accepted the job.
“Being a coach would have been hard for me at that moment, jumping back into the minor league lifestyle with a young child,” Hassan said. “Going into the front office was something different.”
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Hassan and his family moved to Minnesota. He was assistant director of minor league operations for two seasons, then director of player development from 2020-22 before moving up to vice president of hitting development and acquisitions in 2023.
His latest promotion came in January, when he was named assistant general manager under Zoll.
“Alex has been a great addition,” president of baseball and business operations Derek Falvey said. “He’s brought something to every role he’s had with us.”
In an information-driven industry, Hassan is one of those valued executives who can effectively blend major league playing experience with the data.
“I’ve tried to broaden my areas of focus,” Hassan said. “Whether it’s scouting amateur players, MLB roster discussions, free agency or trades, there’s a lot to learn.
“In terms of player development, it’s not just the plan you have for the player. It’s the person, too. You have to consider that. I try to put myself in the shoes of the player who is trying to execute that plan at 7 p.m. You have to find the best balance.”
At 37, Hassan naturally hopes to advance as an executive, though he doesn’t have any particular job in mind. Maybe he will be a general manager someday, but his goals aren’t that specific.
“If you work hard, good things generally will happen. That’s always been the best mentality for me. I don’t have long-term goals. I just want to get better and see where that takes me,” he said.
“I’ve had different roles and enjoyed them all. It seems silly to say, but I really just want to help as many players as I can because I had a lot of people do that for me.
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“That’s all I can ask. I think about all the times I was in the minor leagues in the cage trying to figure it out. You don’t do that just because you want to be rewarded. You do that because you love it. I love being in baseball.”

DEPTH DILEMMA
Do the Red Sox need
another first baseman?
The Red Sox have enviable depth in the outfield, at shortstop, at second base, and even in the rotation, for the first time in a few years.
They also addressed their catching depth by signing veteran Yasmani Grandal to a minor league contract.
What they lack are options at first base beyond Triston Casas.
Utility player Romy Gonzalez is the only other first baseman on the major league roster. Triple A Worcester is using catcher Nathan Hickey there and trying middle infielder Vaughn Grissom to see how that looks.
Casas is off to a slow start, but the Red Sox will give him plenty of runway. The bigger concern is injury. If Casas lands on the injured list, Gonzalez and his 23 games of major league experience at first base are the only choice.
Alex Cora has said Rafael Devers will not play the field this season. It might not be a bad idea to have him take some grounders at first base and see what it looks like.
Maybe the Sox could have Marcelo Mayer give it a shot in Worcester.
A few other observations on the Red Sox:
⋅ The Sox took advantage of the Brewers’ desperate need for pitching with the trade of Quinn Priester last week.
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In addition to a legitimate prospect in 19-year-old outfielder Yophery Rodriguez, the Sox received a competitive-balance draft pick, No. 33 overall.
Now the Sox will pick 15th, 33rd, 75th, and 87th in the draft, making up for the pick they lost to the Astros for signing Alex Bregman.
The Sox took Michael Kopech the last time they had the 33rd pick. That was in 2014.
That the Sox were willing to trade Priester speaks to the much better job they’ve done building starter depth under Craig Breslow.
⋅ Entering the weekend, the Red Sox had nine players with at least one stolen base. The only team with more was the Mariners with 12.
⋅ Here’s another one you didn’t expect. There are only three Red Sox pitchers in the last 30 years who pitched at least five innings in each of their first six major league games. They are Daisuke Matsuzaka (2007), Justin Masterson (2008), and Richard Fitts (2024-25).
⋅ Roman Anthony, who turns 21 on May 13, is the youngest player in Triple A, which is roughly 850 players at a given time. Mayer, 22, is the 15th youngest.
⋅ Kristian Campbell reached safely in his first 13 career games. He was 14 of 44 (.318) with 10 runs, eight walks, six extra-base hits, and five RBIs.
Since 1920, only two Red Sox players age 22 or younger had longer streaks.
Ted Williams reached in 15 straight games in 1939. He went on to drive in 145 runs, have a 1.045 OPS, and finish fourth in the MVP voting behind Joe DiMaggio, teammate Jimmie Foxx, and Bob Feller.
The other was George Scott, who reached in his first 26 games in 1966. The Boomer was an All-Star and finished third in the Rookie of the Year voting behind Tommie Agee and Jim Nash.
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⋅ Campbell’s brother, Kayden, is a junior infielder at Pope High in Marietta, Ga. He’s receiving recruiting attention from several Division 1 schools, TCU among them.
Kayden made it up to Boston for the press conference announcing his brother’s new contract despite having played a game the night before.
⋅ Sam Bregman, Alex’s father, is running for Governor of New Mexico as a Democrat. He will oppose former Secretary of the Interior Deb Haaland in the June 2026 primary.
Bregman is the District Attorney of Bernalillo County.
ETC.
Guerrero took his biggest swing
Vladimir Guerrero Jr. had all the leverage and he sure used it.
After taking a shot but failing to sign free agents Shohei Ohtani and Juan Soto when they were available, the Blue Jays had little choice but to retain their homegrown star first baseman who was born in Canada.
Guerrero and his agents knew he was worth more to the Blue Jays than any other team. They also knew the Jays couldn’t take the chance of allowing Guerrero to become a free agent at a time the Yankees and the Red Sox could use a power-hitting first baseman.
His age — the deal begins next season, when Guerrero will be 27 — also made the deal more palatable.
That led to a 14-year, $500 million contract with no deferrals. Guerrero also landed an incredible $325 million signing bonus spread out over 15 installments.
The structure of the contract protects Guerrero in several ways. Under an international tax agreement, signing bonuses are taxed at a far lower rate in Canada than salary is. (Guerrero saves further as a resident of Florida, which has no state income tax.)
He also would receive the signing bonus payments even in the event of games being canceled because of a work stoppage.
That could prove important with the league and the Players Association already preparing for a fight for when the collective bargaining agreement runs out after the 2026 season.
It speaks to how much baseball has changed that Vladimir Guerrero Sr. made $125.5 million over his 16-year Hall of Fame career. His son will make that every 3½ years through 2039.
The other winner in this deal is Cubs outfielder Kyle Tucker, who now will be the premier hitter on the free agent market this winter.
If the Cubs hope to retain Tucker, it might be wise to act soon. The price is only going to go up.
Extra bases
Octavio Dotel, who died in the nightclub collapse in the Dominican Republic, was one of those players who always seemed to be having a good day. From New York to Los Angeles and 10 cities in between, he arrived with a good fastball and a big smile. Junior Pepén, who calls Red Sox games in Spanish on the radio, said the Jet Set nightclub was a popular spot for Dominican players during the offseason. Dotel and former Nationals player Tony Blanco were among the dead. Blanco reportedly saved the life of former major leaguer Esteban Germán by pushing him away from the collapse … The Twins went into the weekend not having won three consecutive games since Aug. 15-17, 2024 … Javy Baéz played center field for two innings against the White Sox last Sunday. He’s become a utility player for the Tigers at 32 and still has $48 million due from 2026-27 … The “Don’t Call Us Sacramento” Athletics sold out their first home game, then drew fewer than 9,600 for three of the next five games. The team is set to break ground on its new stadium in Las Vegas in June. Plans are for it to open in 2028 … Mike Trout played every inning of the first 12 games for the Angels. He hit only .205, albeit with an .895 OPS, five home runs, and 11 RBIs. “It’s Mike Trout,” manager Ron Washington said. “It will get better. The more he sees pitches, the better it’s going to get. I’m not worried about Mike. As long as we can keep him on the field and keep his presence around here, he’s going to be Mike.” Trout played only 266 games from 2021-24 because of injuries … The Yankees and Adam Ottavino seem to have arrived at a mutually beneficial agreement. Ottavino signed with the Yankees on April 1, appeared in two games, and was designated for assignment on April 4. He elected free agency and was signed again on April 7. He pitched that day, was designated for assignment the next day, and became a free agent. How long before he signs again? … Ian Seymour could soon be making his major league debut with the Rays. The 26-year-old lefthander from St. John’s of Shrewsbury is off to a good start with Triple A Durham, using an effective changeup to complement his modest (90-93-mile-per-hour) fastball … Kaiden McCarthy of Chester, Vt., is one of the best high school players in the Class of 2027, according to Baseball America. The righthander at Vermont Academy has a mid-90s fastball with a curveball and occasional changeup … The annual ALS Awareness Game will be at Fenway Park on April 27 at noon when Boston College hosts Miami. The game has been played annually to honor former BC captain Pete Frates, who died of ALS in 2019. Go to redsox.com/alsgame to purchase tickets … Major League Baseball held a baseball development camp at the Jackie Robinson Training Complex in Vero Beach, Fla., on Friday and Saturday for girls ages 12-14. Participants included Clara Ciampa (Newton), Joanne Nunes (Sandwich), Lilly Silva (Providence), and Mia Sodre (Dracut) … Happy birthday to 2018 World Series MVP Steve Pearce, who is 42. The Red Sox acquired Pearce from the Blue Jays on June 28, 2018. He had a .901 OPS over 50 games and drove in 26 runs. Pearce was then 11 of 38 with six extra-base hits and 11 RBIs over 10 postseason games. He homered twice and drove in three runs in Game 5 of the World Series as the Sox clinched the championship. A knee injury limited Pearce to 29 games in 2019, and he retired before the 2020 season. Also happy birthday to the founding father of this column, Peter Gammons. He turned 80 on Wednesday. “Legend” as Alex Cora appropriately calls him.
Peter Abraham can be reached at peter.abraham@globe.com. Follow him @PeteAbe.