# Bears trade for Jeffrey Simmons

Sports · Heat 10.0 / 10 · 16 shows · 3h 29m airtime

The Tennessee Titans traded Jeffrey Simmons to the Chicago Bears on October 29, 2026, for 2027 and 2028 first-round picks and a 2027 fourth, with a 2028 fifth going to Chicago. Simmons is the first defensive tackle in the common draft era traded for multiple firsts and the oldest defensive player ever traded for multiple firsts. He had 11 sacks and first-team All-Pro honors last season and ranks first among defensive tackles since 2025 in sacks, tackles for loss, pressures, quick pressures and third-down sacks. The Bears, last in defensive tackle production and 23rd in interior pass rush win rate, are treating this year and next, while Caleb Williams is cheap, as their window. The Titans now hold four first-round…

Page: https://boilpoints.com/point/bears_trade_for_jeffrey_simmons_4050386863

## Segments

- [First Take](https://boilpoints.com/u/firsttake), 2026-10-29, 23:58 to 32:21: **Breaks the Simmons trade and its full terms**. Breaks the Simmons-to-Chicago trade on air and works through the full terms once Schefter tweets them: two firsts and a fourth to Tennessee, a 2028 fifth back. Argues the move makes the Bears the NFC North favorite and puts them neck and neck with San Francisco, framing Simmons as the closer Dennis Allen's defense lacked. New angle: The Titans traded Jeffrey Simmons to the Bears for 2027 and 2028 firsts and a 2027 fourth, with a 2028 fifth going to Chicago.
- [First Take](https://boilpoints.com/u/firsttake), 2026-10-29, 0:48 to 2:14: **Reads the trade details and notes the Sweat reunion**. Reads out the Schefter trade details and debates whether the move makes Chicago the NFC's team to beat, weighing the 49ers and the Ben Johnson and Dennis Allen builds. It stays inside the trade already on the record, adding only that Simmons reunites with Montez Sweat.
- [The Right Time with Bomani Jones](https://boilpoints.com/u/therighttimewithbomanijones), 2026-10-29, 30:20 to 33:31: **Reacts to Simmons fitting Allen's front**. Reacts to the Simmons trade, calling him the one difference maker on Tennessee and arguing he fits Dennis Allen's front-dependent defense. Frames it around Caleb Williams' improvement and the Bears' trip to Seattle, staying inside the trade reaction already on the record.
- [The Dan Patrick Show](https://boilpoints.com/u/thedanpatrickshow), 2026-10-29, 13:42 to 14:59: **Questions whether the Titans reach for a QB**. Pivots off the Simmons trade to the Titans' quarterback question: with extra and likely high picks, will Tennessee draft a quarterback, and the warning is against reaching for one the way teams did with Richardson or Locker. Speculation, no new reporting.
- [The Dan Patrick Show](https://boilpoints.com/u/thedanpatrickshow), 2026-10-29, 36:16 to 37:45: **Adds contract and production detail to the trade**. Reports the Simmons trade and adds contract and production detail: he is 29, signed through 2030, and coming off a first-team All-Pro season with 11 sacks. Frames it as a good deal for both sides, with the Bears' picks likely late in the first round. New angle: Simmons is under contract through 2030 and had 11 sacks and first-team All-Pro honors last season.
- [The Athletic Football Show: A show about the NFL](https://boilpoints.com/u/theathleticfootballshowashowaboutthenfl), 2026-10-29, 2:21 to 3:19: **Frames the deal as another Poles swing**. Opens the emergency episode with birthday banter and a quick framing of the Simmons deal as a massive, unsurprising swing for a Bears team with Ryan Poles' history of aggressive trades. Sets up the discussion without adding anything to the record.
- [The Athletic Football Show: A show about the NFL](https://boilpoints.com/u/theathleticfootballshowashowaboutthenfl), 2026-10-29, 3:19 to 6:35: **Argues tackle was the splash spot, not edge**. Argues defensive tackle, not edge, was Chicago's splash spot, and frames Simmons as a top-10 defensive player and Defensive Player of the Year candidate. Compares the price to the Dexter Lawrence and Quinnen Williams deals and notes he turns 30 next summer. Analysis and context, not a new development.
- [The Athletic Football Show: A show about the NFL](https://boilpoints.com/u/theathleticfootballshowashowaboutthenfl), 2026-10-29, 6:35 to 9:33: **Explains the two-year window while Williams is cheap**. Explains the timing of the Simmons trade: a soft-looking NFC and a roster whose premium positions are already filled by young, cheap players, with Williams cheap for at least three more years. Frames it as a two-year window rather than a one-season push. New angle: The Bears see this year and next, while Williams is cheap, as their window.
- [The Athletic Football Show: A show about the NFL](https://boilpoints.com/u/theathleticfootballshowashowaboutthenfl), 2026-10-29, 9:33 to 12:39: **Debates the price against the Colts' precedent**. Calls the Simmons trade an overpay in a vacuum but a defensible one, arguing the Bears have more evidence of readiness than the Colts did when they traded for Daniel Jones. Stays inside the price-and-window argument already on the record.
- [The Athletic Football Show: A show about the NFL](https://boilpoints.com/u/theathleticfootballshowashowaboutthenfl), 2026-10-29, 12:39 to 15:32: **Rewatches Williams' growth to justify the swing**. Rewatches the Bears' previous game and argues Williams has improved his ball placement, rhythm, timing and pocket sense while keeping elite escapability and arm strength, which makes an aggressive move like the Simmons trade easier to justify. Reaction and framing, not a new development.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-29, 5:18 to 18:42: **Reacts to the deal as a win-now signal**. Reacts to the Simmons trade and frames it as the Bears declaring now is the moment, with a Ben Johnson soundbite on Caleb Williams and a replay of Simmons' 2024 visit. Stays inside the deal already on the record.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-29, 35:16 to 36:51: **Jokes with Saturday about Burrow's relief**. Jokes with Jeff Saturday about Joe Burrow's relief that Simmons is no longer on the Titans line, and Saturday's admission that no lineman wants to face him at full strength. Light reaction to the trade, no new development.
- [The Pat McAfee Show](https://boilpoints.com/u/thepatmcafeeshow), 2026-10-29, 10:21 to 25:12: **Retells the Simmons trade and Colts fire sale**. Rapoport walks through the Simmons trade and the Colts' fire sale around it: Chicago pivoted off Buckner once Buckner would only go to San Francisco, and the expiring contracts on Buckner and Nelson explain the smaller returns. Retells the day's reporting with the Bears' odds move as the one fresh figure.
- [The Ryen Russillo Show](https://boilpoints.com/u/theryenrussilloshow), 2026-10-29, 3:41 to 7:42: **Reacts to the Simmons price tag**. Reacts to the Simmons trade with Damien Woody calling it an all-in move and Russillo questioning the price. Adds the contract figure: an extension averaging four years for $109 million, framed against the Sauce Gardner deal. New angle: Simmons' extension averages four years for $109 million.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-29, 42:00 to 44:13: **Recaps a fan's office taunting and Simmons stats**. A Bears fan caller in Seattle recounts the office taunting after the Nelson trade and his celebration when the Simmons news broke, then cites Simmons' defensive tackle rankings since 2025 to argue the first-round picks were worth it. New angle: Since 2025, Simmons ranks first among defensive tackles in sacks, tackles for loss, pressures, quick pressures and third-down sacks.
- [The Shotgun Start](https://boilpoints.com/u/theshotgunstart), 2026-10-29, 0:47 to 3:44: **Frames the Simmons trade as Bears going all in**. Opens the episode with a Victory Friday riff on the Simmons trade - the Bears going all in, the biggest-market debate, the pick-game contrast with the Jets - then pivots to congratulating the Brewers. Reaction and framing, no new development.
- [PTI](https://boilpoints.com/u/pti), 2026-10-29, 11:14 to 16:46: **Calls Simmons the best defensive tackle**. Booger McFarland gives the Simmons trade a full segment, calling him the best defensive tackle in football and the move a Super Bowl-caliber upgrade that puts Chicago alongside Seattle in the NFC. Then a quick run through Browns-Steelers, Packers-Panthers and USC-Ohio State.
- [First Things First](https://boilpoints.com/u/firstthingsfirst), 2026-10-29, 20:24 to 27:19: **Works through non-quarterbacks dealt for two firsts**. Reacts to the Simmons trade and works through the history of non-quarterbacks dealt for multiple firsts, from Mack to Adams to Ramsey. Adds two Bears fan polls and the note that Simmons is the oldest defensive player ever to fetch multiple firsts. New angle: Simmons is the oldest defensive player ever traded for multiple first-round picks.
- [First Things First](https://boilpoints.com/u/firstthingsfirst), 2026-10-29, 1:30:44 to 1:40:41: **Revisits the trade through pre-trade rankings**. Revisits the Simmons trade through the Bears' pre-trade numbers: the 23rd-ranked interior pass rush win rate and the league's worst defensive tackle production. Parkins frames it as all-in on a Super Bowl during Caleb Williams' rookie deal; the dissent runs through the other multi-first trades for defensive players. New angle: The Bears ranked 23rd in interior pass rush win rate and last in defensive tackle production before the trade.
- [The Herd with Colin Cowherd](https://boilpoints.com/u/theherdwithcolincowherd), 2026-10-30, 3:54 to 6:37: **Debates the rookie-contract logic behind the trade**. Reacts to the Simmons trade as breaking news, with Millman cheering the aggression and his co-host arguing the rookie-contract window logic is wrong because Darnold and Hurts won without one. Stays inside the day-one coverage.
- [The Bill Simmons Podcast](https://boilpoints.com/u/thebillsimmonspodcast), 2026-10-30, 4:14 to 10:31: **Adds the Titans' two-first asking price**. Pelissero walks through the Simmons trade from the Titans' side: the two-first asking price that scared teams off, the 49ers checking in before Buckner, and the $57 million guaranteed left on the deal. Adds the Bears' pre-season Dexter trade and Williams' extension eligibility as the clock on the window. New angle: Simmons is due $57 million guaranteed over 2027 and 2028, and the Titans had told teams it would take at least two firsts.
- [The Bill Simmons Podcast](https://boilpoints.com/u/thebillsimmonspodcast), 2026-10-30, 34:28 to 39:05: **Recounts breaking the trade from a stationary bike**. Pelissero tells how he broke the Simmons trade from a stationary bike, then the conversation turns to how a floated price signals a team will sell. Anecdote and market theory, no new development in the trade itself.
- [The Bill Simmons Podcast](https://boilpoints.com/u/thebillsimmonspodcast), 2026-10-30, 53:25 to 56:45: **Debates whether Simmons lifts Chicago to the top tier**. Weighs what Simmons does for a Bears run defense that has held them back two seasons, then argues over whether that lifts Chicago into the NFC's top tier. Dabbundo keeps San Francisco, Seattle and Los Angeles ahead of them; House wants to see it against Seattle first.
- [Pardon My Take](https://boilpoints.com/u/pardonmytake), 2026-10-30, 31:57 to 36:30: **Debates the Simmons trade from the Bears' side**. Debates the Simmons trade from the Bears' side, arguing the two firsts were always going to be spent on defensive line and that Simmons makes the rest of the unit better. Adds one figure not yet on the record: the Titans now hold four first-round picks over the next two years. New angle: The Titans now hold four first-round picks over the next two years.
- [The Herd with Colin Cowherd](https://boilpoints.com/u/theherdwithcolincowherd), 2026-10-30, 2:37 to 13:14: **Runs the history of firsts for defenders**. Runs through the history of teams trading multiple firsts for defensive players - Adams, Ramsey, Mack, Gardner, Parsons, Williams - and reads the Simmons deal as a win-now push around Caleb Williams' rookie contract. Opinion and framing, with the trade terms as background.
- [Nightcap](https://boilpoints.com/u/nightcap), 2026-10-30, 33:26 to 43:32: **Reacts to the Simmons trade and its firsts**. Reacts to the Simmons trade as an all-in Bears move and works through the compensation, then puts a new marker on the record: Simmons is the first defensive tackle in the common draft era traded for multiple firsts. The rest is retelling - his stats, the contract, the Titans' 1-6 record - plus a detour into what Quentin Nelson and… New angle: Simmons is the first defensive tackle in the common draft era traded for multiple first-round picks.
- [Nightcap](https://boilpoints.com/u/nightcap), 2026-10-30, 43:32 to 48:34: **Debates whether Simmons puts Chicago over the top**. Debates whether Simmons puts Chicago over the top in the NFC North and what he unlocks for the defensive coordinator, then runs through the Titans' trades, firings and hires since the 2022 playoff loss. Opinion and recap, with no new development.
- [The Herd with Colin Cowherd](https://boilpoints.com/u/theherdwithcolincowherd), 2026-10-30, 18:44 to 34:21: **Frames the deal as Bears preying on Titans**. Middlekauff frames the Simmons deal as a well-run Bears team preying on a dysfunctional Titans franchise, with the Khalil Mack trade as the comparison. Adds contract specifics: Simmons runs through 2031 at roughly $27 million next year and $29 million the following, with Tennessee already having paid much of this year's salary. New angle: Simmons is under contract through 2031 at about $27 million next year and $29 million the year after.
- [The Herd with Colin Cowherd](https://boilpoints.com/u/theherdwithcolincowherd), 2026-10-30, 1:05:55 to 1:13:14: **Questions the Simmons haul against past trades**. Mailbag answer on the Simmons return: Middlekauff doubts the haul, compares it to the A.J. Brown trade that became Treylon Burks and to the Raiders' Mack and Cooper deals, and says picks do not matter without a quarterback. Stays inside the trade's known terms.
- [Yesterday in Sports](https://boilpoints.com/u/yesterdayinsports), 2026-10-30, 2:36 to 3:47: **Recaps the Simmons trade terms and extension**. Recaps the Simmons trade in about a minute: the pick swap, the 2025 All-Pro nod, the June extension and the win-now framing for a 5-2 Bears team. Stays inside the terms already on the record, then pivots to Brian Thomas Jr. as a deadline name to watch.
- [First Take](https://boilpoints.com/u/firsttake), 2026-10-30, 6:51 to 12:50: **Debates the Simmons trade against Chicago's defense**. Reacts to the Simmons trade and debates whether Chicago is now the NFC's most complete team, splitting over the 49ers, Seahawks and Rams. The one figure not yet on the record: the Bears' defense gives up over six yards per play, the worst in the NFL. New angle: The Bears' defense allows over six yards per play, the worst in the NFL.
- [The Dan Patrick Show](https://boilpoints.com/u/thedanpatrickshow), 2026-10-30, 1:57 to 3:35: **Recaps the Simmons trade and pivots to the Vikings**. Opens the hour with a quick recap of the Simmons trade and the Packers' 27-19 Thursday night win over Carolina, then pivots to the Vikings' NFC North odds and a Jason Garrett story about Joe Montana tape. Passing mention, no new ground.
- [The Dan Patrick Show](https://boilpoints.com/u/thedanpatrickshow), 2026-10-30, 38:14 to 40:21: **Recaps the Simmons trade and caller theories**. A Nashville caller floats a stadium-money conspiracy behind the Simmons trade; Dan calls it a rebuild, doubts the quarterback and runs through the Titans' lost core since 2019. Reaction and theory, no new development.
- [Nightcap](https://boilpoints.com/u/nightcap), 2026-10-30, 14:01 to 20:59: **Debates both sides of the Simmons trade**. Debates the Simmons trade from both sides: Haden calls it a clear Chicago win, Harrison argues Tennessee got the better end given Simmons' age and contract through 2030. Ties it to the Myles Garrett trade and the Rams' record, and stays inside the deal's terms and the stats already on the record.
- [The Dan Le Batard Show](https://boilpoints.com/u/thedanlebatardshow), 2026-10-30, 28:38 to 30:21: **Argues Miami is rebuilding, not tanking**. Turns to the other side of the Simmons trade: with the Dolphins finally winning a game, the Titans are now the worst team in football and the frontrunner for the top draft pick. Zaslow argues Miami is rebuilding, not tanking. New angle: The Titans are now the worst team in football and the frontrunner for the top draft pick.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-30, 8:25 to 12:44: **Argues Simmons is the deadline's biggest move**. Sean McDermott picks the Simmons trade as the most impactful of the deadline line-of-scrimmage moves, arguing the Bears need to get home with four rather than live on Dennis Allen's third-down blitzes. He also floats a Khalil Mack reunion in Chicago. Analysis, not new reporting.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-30, 6:29 to 9:12: **Adds the Giants' prior inquiry and Borgonzi ties**. Fowler's deadline tour lands on the Simmons trade: the Giants had inquired before Tennessee moved him, and Borgonzi's Kansas City ties to Poles may have eased the deal. Also flags Khalil Mack as the buzzing edge name and says Crosby does not want out of Vegas. New angle: The Giants inquired about Jeffrey Simmons before the Titans traded him.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-30, 18:42 to 21:06: **Plays Karras and Nelson reacting to the trade**. Plays clips of Bengals center Ted Karras and new Seahawk Quenton Nelson reacting to the Simmons trade, with Karras saying two hours of anxiety are gone and Nelson saying he cannot get away from Simmons. Reaction, not new reporting.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-30, 20:58 to 23:21: **Argues the price was worth the Super Bowl odds**. Rich spends two minutes on the Simmons price through a shopping analogy: you get what you pay for, and the Bears paid it to raise their Super Bowl odds. Opinion and framing, no new reporting.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-30, 23:24 to 24:45: **Plays Poles explaining the red-level lineman search**. Plays Bears GM Ryan Poles explaining the Simmons trade in his own words: every Super Bowl team since 2018 has had what he calls a red-level interior defensive lineman, and Chicago had been searching for one because the draft and free agency rarely supply it. New angle: Poles says every Super Bowl team since 2018 has had a red-level interior defensive lineman.
- [The Rich Eisen Show](https://boilpoints.com/u/thericheisenshow), 2026-10-30, 24:58 to 28:59: **Frames the deal against the Bengals' Lawrence trade**. Frames the Simmons deal against the Bengals' own decision to flip the 10th overall pick to the Giants for Dexter Lawrence, and notes the Giants are still hunting interior line help after that trade. Closes on whether NFC North rivals answer the Bears' move. New angle: The Bengals sent the 10th overall pick to the Giants for Dexter Lawrence and are 4-2.
- [The Herd with Colin Cowherd](https://boilpoints.com/u/theherdwithcolincowherd), 2026-10-30, 4:28 to 10:22: **Argues late firsts are bust-prone**. Defends the Simmons price by arguing late first-round picks are red-flagged or bust-prone, citing Josh Simmons and Keon Coleman, and says the Bears would pick 28th. Frames the deal as a Powerball-ticket spend around a young coach and a cheap quarterback. Argument and framing, not new reporting.
- [The Herd with Colin Cowherd](https://boilpoints.com/u/theherdwithcolincowherd), 2026-10-30, 11:49 to 15:12: **Defends the Simmons price with draft math**. Brings on a former lineman to defend the Simmons price: most drafts have only about 16 or 17 true first-rounders, and the picks Chicago sent are likely in the high 20s. Frames the trade as championship or bust and praises Williams for playing in structure. New angle: Most GMs say a draft has only about 16 or 17 truly graded first-rounders.
- [PTI](https://boilpoints.com/u/pti), 2026-10-31, 11:07 to 13:30: **Weighs Simmons against Nelson as the bigger addition**. Weighs the Simmons and Nelson trades against each other and lands on Simmons as the more impactful player right away, with a stat line on his pressures this season. The comparison is new; the compensation is a recap. New angle: Simmons has 21 pressures this season, 18 of them against double teams.