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Boston Celtics shock fans: Jrue Holiday heads back to Trail Blazers, ‘Anfernee Simons deal saves millions

Celtics trade defensive ace Jrue Holiday to Portland for Anfernee Simons and picks, reshaping roster amid Jayson Tatum injury concerns.

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Boston Celtics Trade Jrue Holiday to Trail Blazers: Simons Deal Saves Millions | Daily Global Diary
Jrue Holiday during a Celtics game — now set to bring his defensive tenacity back to Portland.

In a move that has already sent ripples through the NBA community, the Boston Celtics have agreed to trade veteran guard Jrue Holiday back to the Portland Trail Blazers in exchange for scoring dynamo Anfernee Simons and two future second-round draft picks, multiple sources told ESPN late Monday.

The trade comes just two years after Portland flipped Holiday to Boston as part of the blockbuster Damian Lillard deal. Now, the Blazers are betting on Holiday’s championship grit and elite perimeter defense to solidify a promising young core.

For the Celtics, the swap is equally strategic. By moving Holiday, Boston will reportedly save nearly $40 million in luxury tax next season, as detailed by ESPN’s Bobby Marks. Simons, 26, arrives on an expiring contract but fits perfectly into coach Joe Mazzulla’s three-point-heavy offensive scheme. The guard has averaged nearly nine attempts from deep per game across his last three seasons — a stat Celtics fans will eagerly embrace.

Holiday’s impact in Boston was undeniable. He was named to the NBA’s All-Defensive Team and shot a career-high 42.9% from three during the 2023-24 campaign. More impressively, he maintained elite shooting splits — 50% from the field, 40% from three, and 90% from the free-throw line — while helping Boston claim another title run before a devastating Jayson Tatum Achilles injury derailed their playoff hopes.

Meanwhile, Portland’s front office has signaled they’re not done yet. Bringing Holiday back reunites them with a seasoned floor general just as they attempt to push past rebuilding status. From January 19 onwards, the Blazers quietly posted a 23-18 record, boasting the league’s third-best defensive rating and suffocating transition defense. Holiday’s presence only strengthens these defensive credentials.

For fans, this trade is more than just numbers. It hints at a busy offseason for the Celtics, who now have added flexibility to shuffle the roster around stars like Tatum and Jaylen Brown. Expect more fireworks as Boston eyes reinforcements to stay in title contention.

One thing’s certain: whether you’re Team Green or a Rip City faithful, Jrue Holiday’s latest twist keeps the NBA rumor mill buzzing — and the Eastern Conference power balance just got a lot more interesting.

Sports

Caleb Williams Impresses, but the Bears’ Late-Game Decisions Raise Eyebrows

One impossible touchdown changed everything — but Chicago’s season may have been decided by what happened next

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Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years

For one breathtaking moment, football stopped making sense.

With seconds left in a divisional-round playoff game, Caleb Williams launched a prayer — a 50-plus-yard, off-balance, back-foot moon shot — and somehow, impossibly, it found Cole Kmet in the end zone. It was the kind of touchdown that instantly joins NFL folklore, the sort of play fans remember for decades.

Suddenly, the Chicago Bears were one extra point away from tying the Los Angeles Rams — a scenario no one could have imagined just moments earlier.

And that’s when the question arrived, loud and unavoidable:

Why not go for two?

The dream-big argument

If Chicago converts the two-point try, the Rams are done. Season over. The Bears move one game away from the Super Bowl, potentially facing either a second-year quarterback or an injury replacement in the AFC. No matchup in the NFL is easy, but this was a window — and those windows don’t stay open long.

Ask Aaron Rodgers or Dan Marino how rare Super Bowl chances truly are. Between them, 38 seasons, one Super Bowl appearance each. Even greatness doesn’t guarantee multiple shots.

Momentum, belief, shock value — everything screamed end it now. One play. One decision. Push all the chips to the middle.

But football decisions aren’t made in the clouds. They’re made in film rooms.

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years


Why Chicago didn’t gamble

Offensive coordinator Ben Johnson didn’t flinch. Replays showed him calm, unmoved, almost indifferent to the miracle unfolding. He knew the touchdown created options — but also responsibility.

Because miracles don’t stack.

Just minutes earlier, Chicago had first-and-goal at the Rams’ 5-yard line. Three ineffective runs by De’Andre Swift and a failed fourth-down pass told Johnson everything he needed to know about his short-yardage confidence.

After the game, Johnson explained it plainly.

“Our goal-to-go situations hadn’t gone very cleanly,” he said. “Our inside-the-5 plan hadn’t worked out like we hoped. I just felt better about taking our chances in overtime.”

There was also time left — 13 seconds and two Rams timeouts. One explosive play, maybe a penalty, and Los Angeles could still have stolen it with a field goal even after a failed conversion.

So Chicago chose survival over glory.

How it unraveled anyway

The Bears lived to fight in overtime — and then watched their season collapse anyway. A brutal interception. A defensive breakdown. Game over.

And just like that, Williams-to-Kmet joined a heartbreaking fraternity: iconic plays that didn’t change the ending. Think Kurt Warner to Larry Fitzgerald in Super Bowl XLIII. Think Julio Jones and that impossible toe-tap in Super Bowl LI.

Legendary moments — frozen in time — attached to losses.

So… was it the wrong call?

Emotionally? Maybe.

Strategically? Probably not.

Coaches don’t get paid to chase vibes. They get paid to trust evidence. And Chicago’s evidence said a single, all-or-nothing snap wasn’t the best bet.

That doesn’t make it satisfying. It just makes it honest.

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years


What this moment really means for Chicago

The Bears don’t leave this game empty-handed. They leave with something rarer than a win: belief.

You can’t build a franchise on miracle throws — but you can build a culture on refusing to quit. This team fought until the very last second, and that matters more than fans often admit.

Williams will be just 24 entering the 2026 season. Think about what he might look like at 27, 28, 29. There are no guarantees — Rodgers and Marino taught us that — but this is as good a foundation as any team could ask for.

Years from now, if Chicago is lucky, Williams-to-Kmet won’t be remembered as a cruel “what if.”

It will be remembered as the beginning.

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Sports

A Strong Night for Caleb Williams Ends With Doubts About the Bears’ Late Decisions

One impossible touchdown changed everything — but Chicago’s season may have been decided by what happened next

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Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years

For one breathtaking moment, football stopped making sense.

With seconds left in a divisional-round playoff game, Caleb Williams launched a prayer — a 50-plus-yard, off-balance, back-foot moon shot — and somehow, impossibly, it found Cole Kmet in the end zone. It was the kind of touchdown that instantly joins NFL folklore, the sort of play fans remember for decades.

Suddenly, the Chicago Bears were one extra point away from tying the Los Angeles Rams — a scenario no one could have imagined just moments earlier.

And that’s when the question arrived, loud and unavoidable:

Why not go for two?

The dream-big argument

If Chicago converts the two-point try, the Rams are done. Season over. The Bears move one game away from the Super Bowl, potentially facing either a second-year quarterback or an injury replacement in the AFC. No matchup in the NFL is easy, but this was a window — and those windows don’t stay open long.

Ask Aaron Rodgers or Dan Marino how rare Super Bowl chances truly are. Between them, 38 seasons, one Super Bowl appearance each. Even greatness doesn’t guarantee multiple shots.

Momentum, belief, shock value — everything screamed end it now. One play. One decision. Push all the chips to the middle.

But football decisions aren’t made in the clouds. They’re made in film rooms.

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years


Why Chicago didn’t gamble

Offensive coordinator Ben Johnson didn’t flinch. Replays showed him calm, unmoved, almost indifferent to the miracle unfolding. He knew the touchdown created options — but also responsibility.

Because miracles don’t stack.

Just minutes earlier, Chicago had first-and-goal at the Rams’ 5-yard line. Three ineffective runs by De’Andre Swift and a failed fourth-down pass told Johnson everything he needed to know about his short-yardage confidence.

After the game, Johnson explained it plainly.

“Our goal-to-go situations hadn’t gone very cleanly,” he said. “Our inside-the-5 plan hadn’t worked out like we hoped. I just felt better about taking our chances in overtime.”

There was also time left — 13 seconds and two Rams timeouts. One explosive play, maybe a penalty, and Los Angeles could still have stolen it with a field goal even after a failed conversion.

So Chicago chose survival over glory.

How it unraveled anyway

The Bears lived to fight in overtime — and then watched their season collapse anyway. A brutal interception. A defensive breakdown. Game over.

And just like that, Williams-to-Kmet joined a heartbreaking fraternity: iconic plays that didn’t change the ending. Think Kurt Warner to Larry Fitzgerald in Super Bowl XLIII. Think Julio Jones and that impossible toe-tap in Super Bowl LI.

Legendary moments — frozen in time — attached to losses.

So… was it the wrong call?

Emotionally? Maybe.

Strategically? Probably not.

Coaches don’t get paid to chase vibes. They get paid to trust evidence. And Chicago’s evidence said a single, all-or-nothing snap wasn’t the best bet.

That doesn’t make it satisfying. It just makes it honest.

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years


What this moment really means for Chicago

The Bears don’t leave this game empty-handed. They leave with something rarer than a win: belief.

You can’t build a franchise on miracle throws — but you can build a culture on refusing to quit. This team fought until the very last second, and that matters more than fans often admit.

Williams will be just 24 entering the 2026 season. Think about what he might look like at 27, 28, 29. There are no guarantees — Rodgers and Marino taught us that — but this is as good a foundation as any team could ask for.

Years from now, if Chicago is lucky, Williams-to-Kmet won’t be remembered as a cruel “what if.”

It will be remembered as the beginning.

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Sports

Caleb Williams Did His Part But Did the Bears Overthink the Finish

One impossible touchdown changed everything — but Chicago’s season may have been decided by what happened next

Published

on

By

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years

For one breathtaking moment, football stopped making sense.

With seconds left in a divisional-round playoff game, Caleb Williams launched a prayer — a 50-plus-yard, off-balance, back-foot moon shot — and somehow, impossibly, it found Cole Kmet in the end zone. It was the kind of touchdown that instantly joins NFL folklore, the sort of play fans remember for decades.

Suddenly, the Chicago Bears were one extra point away from tying the Los Angeles Rams — a scenario no one could have imagined just moments earlier.

And that’s when the question arrived, loud and unavoidable:

Why not go for two?

The dream-big argument

If Chicago converts the two-point try, the Rams are done. Season over. The Bears move one game away from the Super Bowl, potentially facing either a second-year quarterback or an injury replacement in the AFC. No matchup in the NFL is easy, but this was a window — and those windows don’t stay open long.

Ask Aaron Rodgers or Dan Marino how rare Super Bowl chances truly are. Between them, 38 seasons, one Super Bowl appearance each. Even greatness doesn’t guarantee multiple shots.

Momentum, belief, shock value — everything screamed end it now. One play. One decision. Push all the chips to the middle.

But football decisions aren’t made in the clouds. They’re made in film rooms.

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years


Why Chicago didn’t gamble

Offensive coordinator Ben Johnson didn’t flinch. Replays showed him calm, unmoved, almost indifferent to the miracle unfolding. He knew the touchdown created options — but also responsibility.

Because miracles don’t stack.

Just minutes earlier, Chicago had first-and-goal at the Rams’ 5-yard line. Three ineffective runs by De’Andre Swift and a failed fourth-down pass told Johnson everything he needed to know about his short-yardage confidence.

After the game, Johnson explained it plainly.

“Our goal-to-go situations hadn’t gone very cleanly,” he said. “Our inside-the-5 plan hadn’t worked out like we hoped. I just felt better about taking our chances in overtime.”

There was also time left — 13 seconds and two Rams timeouts. One explosive play, maybe a penalty, and Los Angeles could still have stolen it with a field goal even after a failed conversion.

So Chicago chose survival over glory.

How it unraveled anyway

The Bears lived to fight in overtime — and then watched their season collapse anyway. A brutal interception. A defensive breakdown. Game over.

And just like that, Williams-to-Kmet joined a heartbreaking fraternity: iconic plays that didn’t change the ending. Think Kurt Warner to Larry Fitzgerald in Super Bowl XLIII. Think Julio Jones and that impossible toe-tap in Super Bowl LI.

Legendary moments — frozen in time — attached to losses.

So… was it the wrong call?

Emotionally? Maybe.

Strategically? Probably not.

Coaches don’t get paid to chase vibes. They get paid to trust evidence. And Chicago’s evidence said a single, all-or-nothing snap wasn’t the best bet.

That doesn’t make it satisfying. It just makes it honest.

Caleb Williams’ miracle touchdown gave the Bears hope — and a decision that will be debated for years


What this moment really means for Chicago

The Bears don’t leave this game empty-handed. They leave with something rarer than a win: belief.

You can’t build a franchise on miracle throws — but you can build a culture on refusing to quit. This team fought until the very last second, and that matters more than fans often admit.

Williams will be just 24 entering the 2026 season. Think about what he might look like at 27, 28, 29. There are no guarantees — Rodgers and Marino taught us that — but this is as good a foundation as any team could ask for.

Years from now, if Chicago is lucky, Williams-to-Kmet won’t be remembered as a cruel “what if.”

It will be remembered as the beginning.

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