During Don Sweeney’s tenure as general manager of the Boston Bruins, one thing has repeatedly become evident: the NHL Entry Draft hasn’t been a strong suit for him or his scouting team. While Boston has occasionally struck gold in the later rounds—uncovering some mid-draft gems—the frequent fate of their first-round selections tells a different story. Often, these picks have been surrendered at the trade deadline in hopes of bolstering a Stanley Cup run. In some years, that strategy hasn’t panned out, and the result has been clear: a noticeably sparse pipeline of emerging talent awaiting its chance to step onto the NHL stage.
To be fair, Sweeney’s willingness to gamble on those early picks does reflect a front office focused on immediate success. Yet the downside of that approach has surfaced repeatedly—most notably through high-profile draft misses. One infamous example is the 2015 Entry Draft, where a particularly disappointing first-round selection left Bruins fans shaking their heads. Against that backdrop, the 2016 draft is often overlooked—but taking a closer look, that year holds its own layer of what-ifs and near-misses.
The 2016 Draft: A Road Not Taken
Back in 2016, as the first round drew to a close, Sweeney chose forward Trent Frederic with a late first-round pick. Frederic wasn’t widely regarded as a locked-and-loaded prospect at that stage, raising eyebrows among draft-watchers. Meanwhile, available on the board remained Jordan Kyrou—a dynamic center later selected in the early second round by another franchise. Looking backward with today’s knowledge, one can’t help but wonder: what if Boston had opted for Kyrou instead?
Frederic arrived in Boston’s system and showed flashes of promise—enough that the team retained him through multiple coaching regimes. Although he didn’t always thrive under former coach Bruce Cassidy, he found some rhythm with Jim Montgomery. Still, that momentum didn’t last; by March of the season in question, the Bruins packaged Frederic in a trade to Edmonton. Now firmly entrenched in Oilers colors, Frederic recently earned a contract extension, signaling Edmonton views him as a steady piece in their future.
Kyrou’s trajectory, however, matters more in this “what-if” scenario. Rapidly emerging as a prominent offensive talent in the NHL, Kyrou—rumored to be available in trade markets—has become exactly the kind of difference-maker Boston lacked. If the Bruins had drafted and developed him, his playmaking and scoring prowess would have filled a crucial void, especially with the recent departures of long-standing pillars like Patrice Bergeron and David Krejci.
At those critical forward positions, Boston has often found themselves scrambling. The departure of Bergeron and Krejci left them bereft of elite center depth—and, importantly, without the elite distributor that a player like Kyrou could have offered. Team star David Pastrnak, for example, might have benefited greatly from a top-tier playmaking pivot. Instead, the front office has been left chasing solutions, hoping to remedy the gap at center through trades or free agency.
A Pattern of Passing Up Potential
Sweeney passing on Kyrou is hardly an isolated oversight. It’s part of a pattern that stretches back to the mid-2010s, most notably the more scrutinized 2015 Draft. Each missed opportunity adds weight to the argument that Boston’s top-end draft misses have mired the organization in reactive roster construction, leaning on trades instead of homegrown talent.
By comparing Kyrou’s evolution since 2016 to where Boston stands today, the magnitude of the misstep becomes clear:
Depth at Center: A player like Kyrou would’ve shored up the Bruins’ center corps during a turbulent period, providing internal support during playoff runs and bridging the gap left by departing veterans.
Qualitative Fit: His strengths align with the type of skill set Boston needs—dynamic offense, strong transition play, and a balance of creativity and scoring instinct.
Long-Term Value: Had Boston drafted and cultivated Kyrou, there’s a hypothetical scenario in which he remains a core contributor, either in a Bruins jersey or as a trade chip of equal or greater value.
Instead, the Bruins have repeatedly found themselves in the market—investing draft capital or trading for the missing blueprint parts with no guarantee of success. The irony is that the cost of acquiring external forward talent often amounts to far more than what Boston surrendered when they swapped away those draft positions in the first place.
Why Mid-Round Success Can’t Mask Early-Round Misfires
Let’s be clear: Boston hasn’t entirely failed in drafting under Sweeney. The front office has unearthed legitimate contributors in rounds two, three, and beyond. These players have bolstered the roster, filled out depth charts, and occasionally contributed meaningfully to postseason runs.
Still, those second-tier finds haven’t counterbalanced the missed opportunity cost of top-tier selections. Every misfire in the first round doesn’t just represent that pick—it erodes organizational depth, limits future trade chips, and perpetuates a culture rooted more in short-term gains than sustained stronghold through drafting.
That pattern is precisely why the Kyrou scenario sticks: on paper, he wasn’t a massive reach—he was there, available, and suited Boston’s style. Yet the Bruins overlooked him, tilted by a mindset focused squarely on immediate help rather than long-term development.
What If Boston Drafted Kyrou?
If Boston had selected and developed Jordan Kyrou starting in 2016, how might their landscape look now?
1. Center Corps Boost
A natural center, Kyrou would have been groomed in Providence or Boston shortly after. As Krejci and Bergeron wound down, Kyrou steps into a growing role—lessening the urgency for high-dollar trade chips or risky acquisitions.
2. Locker Room Continuity
Rather than having to replace two generational talents in Houston and Krejci with a smattering of journeyman fits or piecemeal deals, Kyrou becomes that internal bridge, maintaining the offense’s rhythm and retaining core chemistry.
3. Strategic Asset Flexibility
If the Bruins were already loaded up front, Kyrou could’ve morphed into a valuable trade piece—one whose market logic transcends his on-ice value, bringing back multiple assets in return. The alternative? Boston sold high on future picks that never matured.
4. Playoff Tenacity
With Kyrou in the mold of a Pastrnak-compatible center, Boston’s offense gains a new threat—an unpredictable, electric playmaker emerging at crunch time. That element could have made the difference in closely contested playoff series.
In essence, Kyrou could’ve smoothed Boston’s transition from a legacy-laden roster to their post-Bergeron era. Instead, at times the Bruins have looked disjointed, scrambling for elite forwards, and relying on Soglin-shaped band-aid fixes to paper over the gap.
The Opportunity Cost—Missed Value That Still Lingers
Under Sweeney, Boston’s draft board has often prioritized immediate upside over nascency. Even when the front office later strikes gold in later rounds, those draftees typically fill support roles, not fill the vacuum left by franchise icons. The organization has paid a price:
Diminished top-end depth
Without first-round floor picks or standout foundation pieces, Boston’s system lacks homegrown candidates for top-line or top-six roles—which in turn has forced the team to make aggressive, expensive moves.
Roster volatility
When core veterans retire or depart, the Bruins scramble for replacements rather than relying on internal transitions. The result? A team that’s inconsistent across key cycles.
Boston’s success hasn’t been halted by these drafting missteps—it’s a Stanley Cup contender—but there’s a pervasive question: what might they achieve with a homegrown star in the mold of Kyrou or a similar talent? Those first-round misses may be the hidden barrier between perennial contender and long-term dynasty.
Concluding Thoughts: The Importance of Balanced Draft Strategy
The Boston Bruins under Don Sweeney have traveled a familiar route: short-term gain over long-term cultivation. While that pathway is understandable—no one sacrifices winning today for uncertainty tomorrow—the draft is where foundation meets future. In Kyrou’s case, Boston held the chance to land a dynamic center that fit exactly where they needed reinforcement. Opting for Frederic—a mid-to-late first-round hopeful with a different upside profile—reveals the friction between development philosophy and immediate needs.
Our strongest takeaway? For the Bruins to elevate from “always in the hunt” to “dynasty-level benchmark,” they must fully embrace the draft’s potential. That means harnessing first-round selections not just to trade, but to build pillars—players who grow from prospectdom into franchise linchpins. Because the alternative—continuing to trade away those picks, only later piecing together makeshift assets—is simply unsustainable at the highest level.
In summary, the path not taken in 2016 isn’t just a footnote; it’s a blueprint for reassessing a culture. Jordan Kyrou’s rise is the living proof that sometimes the obvious choice on draft day matters most when the future is written.
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