Pete Crow Armstrong Girlfriend: Her Career, Education and Relationship With the Cubs Star
Chicago Cubs center fielder Pete Crow-Armstrong recently celebrated another major achievement in his baseball career, winning his second consecutive Gold Glove Award and the National League Platinum Glove following a historic 40-home-run, 40-stolen-base season. His girlfriend, Madeline Kennedy, joined him for the Gold Glove celebrations in New York, attracting attention after the couple shared photographs from the event on social media. Their appearance has renewed interest in Crow-Armstrong’s romantic life and his previous relationship with Hailey Lavelle.
Pete Crow-Armstrong’s girlfriend is Madeline Kennedy, a Chicago-based business professional who works in advertising and client development. The couple publicly appeared together at the MLB All-Star Game in July 2026, confirming a new chapter in the baseball player’s personal life. Crow-Armstrong previously dated Hailey Lavelle, whom he met at Vanessa Hudgens and Cole Tucker’s wedding in December 2023.
Who Is Pete Crow-Armstrong’s Girlfriend Madeline Kennedy?
Madeline Kennedy is an American business professional with experience in advertising, marketing, public relations and client management.
She is based in Chicago, Illinois, where she has developed a career working with companies in digital marketing and business development.
Kennedy currently works as a client growth executive at Epsilon, a marketing and advertising technology company.
Her professional responsibilities involve supporting client relationships and developing business opportunities.
Although she has established a career outside professional sports, Kennedy has attracted attention through her relationship with the Chicago Cubs outfielder.
Her appearances alongside Crow-Armstrong at major baseball events have introduced her to a wider audience.
Madeline Kennedy Attends the Gold Glove Awards With Pete Crow-Armstrong
Pete Crow-Armstrong and Madeline Kennedy attended the Rawlings Gold Glove Award ceremony in New York City on November 6, 2026.
The event celebrated outstanding defensive performances across Major League Baseball.
Crow-Armstrong received recognition after winning his second consecutive National League Gold Glove Award.
He also earned the National League Platinum Glove, an additional honor recognizing exceptional defensive performance.
Kennedy accompanied him to the ceremony, wearing a navy ribbed knit maxi dress.
Crow-Armstrong wore a navy cable-knit cardigan, white shirt and patterned tie.
The baseball player later shared photographs from the evening through his Instagram Stories.
Their appearance offered fans another glimpse into a relationship that has become increasingly visible during the season.
When Did Pete Crow-Armstrong and Madeline Kennedy Start Dating?
Pete Crow-Armstrong and Madeline Kennedy became publicly associated as a couple during the summer of 2026.
They attended the MLB All-Star Game red carpet together in Philadelphia on July 14.
The appearance attracted attention because Crow-Armstrong had previously attended the same event with his former girlfriend, Hailey Lavelle.
Although the couple’s exact relationship starting date has not been publicly established, their All-Star Game appearance confirmed that they were spending time together romantically.
Since then, Kennedy has appeared in additional photographs connected to Crow-Armstrong’s baseball career.
Their relationship has remained relatively private despite growing public interest.
Neither has provided an extensive account of how they first met.
Madeline Kennedy’s Education and Career
Madeline Kennedy attended Indiana University Bloomington, graduating in 2017 with a degree in communication and media studies.
During her studies, she participated in student organizations and gained experience in public relations.
She also spent time studying abroad at the Universidad de Sevilla in Spain.
Before beginning her professional career, Kennedy attended Joliet Catholic Academy in Illinois.
She participated in track and field during her school years.
Following graduation, Kennedy worked in several marketing and client-focused positions.
Her early professional experience included working with the Chicago Bulls in ticket sales.
She subsequently pursued opportunities in public relations and digital advertising.
Kennedy later held positions at PerkSpot and Aditude before joining Epsilon in January 2023.
Her professional background reflects an established career independent of her relationship with Crow-Armstrong.
Pete Crow-Armstrong and Madeline Kennedy at the MLB All-Star Game
The couple made one of their first widely reported public appearances together at the MLB All-Star Game red carpet in Philadelphia.
Crow-Armstrong attended the July 2026 event after earning his second consecutive All-Star selection.
Kennedy accompanied him wearing a brown satin halter dress and carrying a pink handbag.
Crow-Armstrong chose a black leather jacket, beige trousers and glasses.
Their appearance attracted attention from baseball fans who had followed his previous relationship.
The Chicago Cubs also shared photographs and videos from the red carpet through the team’s social media accounts.
For Kennedy, the event represented an important introduction to the public side of Crow-Armstrong’s professional career.
Who Is Pete Crow-Armstrong’s Ex-Girlfriend Hailey Lavelle?
Before dating Madeline Kennedy, Pete Crow-Armstrong was in a relationship with Hailey Lavelle.
Lavelle is a licensed esthetician who has worked in the beauty and skincare industry.
Their romance became widely known during the 2025 baseball season.
Crow-Armstrong previously revealed that he met Lavelle at the wedding of actress Vanessa Hudgens and former professional baseball player Cole Tucker.
The wedding took place in Tulum, Mexico, in December 2023.
Crow-Armstrong attended because of his friendship with Cole Tucker’s younger brother, Carson.
The unexpected meeting eventually developed into a romantic relationship.
The couple dated for approximately a year and a half before their relationship ended.
Pete Crow-Armstrong and Hailey Lavelle’s Relationship Timeline
Crow-Armstrong and Lavelle began dating after meeting in December 2023.
They occasionally shared photographs and affectionate messages through social media.
Their relationship attracted greater attention as Crow-Armstrong became one of the Chicago Cubs’ most recognizable young players.
In July 2025, Lavelle accompanied him to his first MLB All-Star Game in Atlanta.
The couple walked the red carpet together, wearing coordinated outfits.
Crow-Armstrong joked during an interview that he was happy to have an attractive partner beside him while navigating his first major red-carpet appearance.
Their appearance became a popular moment among Cubs supporters.
However, by July 2026, Crow-Armstrong was publicly appearing with Madeline Kennedy.
Neither Crow-Armstrong nor Lavelle has provided a detailed public explanation for their breakup.
Why Did Pete Crow-Armstrong and Hailey Lavelle Break Up?
The specific reason Pete Crow-Armstrong and Hailey Lavelle ended their relationship has not been publicly confirmed.
The former couple appeared together at the 2025 MLB All-Star Game and were still being described as partners in media coverage during the following months.
However, Crow-Armstrong’s appearance with Madeline Kennedy at the 2026 All-Star Game established that his romantic life had changed.
Neither party has publicly discussed the circumstances surrounding the separation in detail.
There is also no verified information establishing that a particular disagreement or incident caused the breakup.
For that reason, claims about the reasons behind their separation should be treated cautiously.
Madeline Kennedy’s Friendship With Other Cubs Families
Madeline Kennedy has also spent time with people connected to the Chicago Cubs organization.
In September 2026, she appeared in a social media photograph shared by Reagan Bregman, the wife of Cubs infielder Alex Bregman.
The two women enjoyed an outing on Lake Michigan with the Chicago skyline visible in the background.
Kennedy wore a navy bikini top and a patterned wrap skirt.
The photograph attracted attention because it suggested that she had become familiar with other members of the Cubs’ extended social circle.
Reagan Bregman is an entrepreneur and wellness personality who frequently shares family and lifestyle content online.
Their outing offered another glimpse into Kennedy’s life beyond public appearances with Crow-Armstrong.
Who Is Pete Crow-Armstrong?
Pete Crow-Armstrong is an American professional baseball player who serves as a center fielder for the Chicago Cubs.
He was born on March 25, 2002, in Sherman Oaks, California.
He is 24 years old as of November 2026.
Crow-Armstrong attended Harvard-Westlake School in Los Angeles, where he developed into a highly regarded baseball prospect.
The New York Mets selected him with the 19th overall pick in the 2020 MLB Draft.
In July 2021, he was traded to the Chicago Cubs as part of a deal involving shortstop Javier Báez.
Crow-Armstrong made his Major League Baseball debut on September 11, 2023.
His combination of speed, defensive ability and improving offensive production helped establish him as an important member of the Cubs.
Pete Crow-Armstrong’s Family Background
Pete Crow-Armstrong comes from a family with connections to the entertainment industry.
His mother is actress Ashley Crow, known for her appearances in television and film.
His father is actor Matthew John Armstrong, who has also worked in television.
Growing up in Los Angeles, Crow-Armstrong was familiar with the entertainment industry through his parents.
However, he developed his own professional interests through baseball.
He attended Harvard-Westlake School, which has produced several notable professional athletes.
His family has supported his development throughout his baseball career.
Despite his parents’ entertainment backgrounds, Crow-Armstrong has built his public identity primarily through his achievements in Major League Baseball.
Pete Crow-Armstrong’s Historic Baseball Season
Crow-Armstrong enjoyed a remarkable 2026 season with the Chicago Cubs.
He became the first player in franchise history to record at least 40 home runs and 40 stolen bases in a single season.
The achievement placed him among a small group of Major League Baseball players to reach the milestone.
He finished the regular season with 45 home runs, 41 stolen bases and 107 runs batted in.
His defensive performances were equally impressive.
He earned his second consecutive Gold Glove Award and was recognized with the National League Platinum Glove.
The achievements strengthened his reputation as one of baseball’s most exciting young outfielders.
Earlier in the year, Crow-Armstrong signed a six-year, $115 million contract extension with the Cubs.
His growing success has also increased public interest in his life away from baseball.
Is Pete Crow-Armstrong Married?
Pete Crow-Armstrong is not publicly known to be married.
He has been romantically linked to Madeline Kennedy since their appearance together at the 2026 MLB All-Star Game.
The couple has not announced an engagement or wedding.
Crow-Armstrong was previously in a relationship with Hailey Lavelle.
Although his romantic life has attracted increasing attention, he has generally avoided discussing private relationship details extensively.
His current relationship with Kennedy appears to be an important part of his personal life, but no verified announcement has established plans for marriage.
Pete Crow-Armstrong and Madeline Kennedy’s Relationship Today
As of November 2026, Pete Crow-Armstrong is dating Madeline Kennedy, a Chicago-based marketing and business development professional.
The couple attended the MLB All-Star Game together in July and appeared at the Gold Glove Awards in November.
Kennedy has also developed connections with other people associated with the Chicago Cubs.
Crow-Armstrong previously dated Hailey Lavelle, whom he met at Vanessa Hudgens and Cole Tucker’s wedding in 2023.
Their relationship ended before he publicly appeared with Kennedy in 2026.
For readers searching for Pete Crow-Armstrong’s girlfriend, Madeline Kennedy is his current publicly identified partner. While the couple keeps many aspects of their romance private, their appearances at major baseball events have confirmed their relationship and introduced Kennedy to Cubs fans.
